Handbook of Ultraviolet andVisible Absorption Spectraof Organic Compounds

Kenzo HirayamaFuji Photo Film Research LaboratoriesOdawara, Japan

PLENUM PRESS DATA DIVISION NEW YORK 1967

Library of Congress Catalog Card Number 66-24948

1967 Plenum Press Data DivisionA Division of Plenum Publishing Corporation227 West 17 Street, New York, N. Y. 10011All rights reserved

No part of this publication may be reproduced in anyform without written permission from the publisherPrinted in the United States of America

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Contents

Introduction ......................................................................................................................... 1

Explanation on Notation and Arrangement ...................................................................... 4

Table 1. Absorption Maximum from Chemical Structure ................................................ 9 Abbreviations and Symbols .............................................................................................................. 9 List of Chromophores ........................................................................................................................ 10 1. No Chromophore ....................................................................................................................... 20 2. (C:C)-Chromophores ................................................................................................................. 23 3. (C:C)-Chromophores and Cumulenoid Chromophores ............................................................ 31 4. (N:N)-, (O-N:N)-, and (N:N:N)-Chromophores .......................................................................... 35 5. (N:C)-Chromophores ................................................................................................................. 36 6. (N:C),- (N:C:N)-, and (N:N:C)-Chromophores ........................................................................... 50 7. (O:C)-Chromophores ................................................................................................................. 51 8. (O:C-N)-Chromophores ............................................................................................................. 69 9. (O:C-O)-Chromophores ............................................................................................................. 71 10. Other (O:C-X)-Chromophores and (O:C:C)-Chromophores ..................................................... 82 11. (O:N)- and (O:N-O)-Chromophores .......................................................................................... 84 12. Other Aliphatic Chromophores .................................................................................................. 87 13. Metallocene- and (X:X:5:X)-Chromophores .............................................................................. 88 14. (6)-Chromophores without Other Conjugated Unit Chromophores .......................................... 89 15. (6)(C:C)-, (6)(C:C)-, and (6)(Cumulenoid)-System ................................................................... 120 16. (6)(N:N)-, (6)(O-N:N)-, and (6)(N:N:N)-System ......................................................................... 128 17. (6)(N:C)-System ......................................................................................................................... 142 18. (6)(N:C)-, (6)(N:C:C)-, and (6)(P:P)-System ............................................................................. 153 19. (6)(O:C)-System ........................................................................................................................ 155 20. (6)(O:C-N)-System .................................................................................................................... 182 21. (6)(O:C-O)- and Other (6)(O:C-X)-Systems .............................................................................. 184 22. (6)(O:N)-System ........................................................................................................................ 200 23. (6)(O:N-O)-System .................................................................................................................... 202

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24. Other Aromatic Systems with (6) ............................................................................................... 225 25. (X:6:X)-Chromophores .............................................................................................................. 226 26. (7:X)- and (X:X:7:X)-Chromophores .......................................................................................... 233 27. (65:X)-, (66)-, and (X:66:X)-Chromophores .............................................................................. 238 28. Other Chromophores Consisting of 2 Carboaromatic Condensed Rings ................................ 267 29. Chromophores Consisting of 3 Carboaromatic Condensed Rings .......................................... 274 30. Chromophores Consisting of 4 Carboaromatic Condensed Rings .......................................... 292 31. Other Carboaromatic Chromophores ........................................................................................ 308 32. (N5)-Chromophores ................................................................................................................... 319 33. (N6)-and (N6:X)-Chromophores ................................................................................................ 322 34. (N65)-, (N65:X)-, and (X:N65:X)-Chromophores ...................................................................... 338 35. (N66)-, (N66:X)-, and (X:N66:X)-Chromophores ...................................................................... 345 36. Other N1 Aromatic Chromophores ............................................................................................ 362 37. (N25)-, (N25:X)-, (X:N25:X)-, and (X:X:N25:X)-Chromophores .................................................. 372 38. (N26)-, (N26:X)-, and (X:N26:X)-Chromophores ........................................................................ 376 39. Other N2-Aromatic Chromophores ............................................................................................ 401 40. N3-Aromatic Chromophores ...................................................................................................... 415 41. N4-Aromatic Chromophores ...................................................................................................... 423 42. Other Aromatic Chromophores with N Hetero-atoms ............................................................... 441 43. Aromatic Chromophores with P or As Hetero-atom(s) ............................................................. 443 44. (O5)-and (X:O5:X)-Chromophores ............................................................................................ 444 45. (O6)-and (O6:X)-Chromophores ............................................................................................... 453 46. Other Aromatic Chromophores with O Hetero-atom(s) ............................................................ 457 47. Aromatic Chromophores with O and N Hetero-atoms .............................................................. 469 48. Aromatic Chromophores with S Hetero-atom(s) ....................................................................... 480 49. Aromatic Chromophores with S and N Hetero-atoms .............................................................. 492 50. Other Heteroaromatic Chromophores ....................................................................................... 506

Table 2. Absorbing Chromophore from Absorption Maximum ...................................... 509 max.:

INTRODUCTION

Ultraviolet and visible absorptions of organic compounds are characteristic ofabsorbing systems that consist of a so-called chromophore group and the auxochromic groupsbonded to it, rather than the chemical structure of the molecule as a whole.

For example, the ultraviolet absorption maximum of the cholestadienone isomer (I) isclose to that, of (II), but entirely different from those of the other isomers, (III), (IV),and (V)o However, it is very close to the absorption maximum of a nonsteroidal,4-methyl-6-(2,6,6-trimethyl-2-cyclohexenyl)-3,5-hexadien-2-one (VI). This is naturalbecause the absorbing system is the same in (I), (II), and (VI), but is quite differentfrom those of (III), (IV), and (V)0

(I) cholesta-4,6-dien-3-one

*max* 285m^

In that publication, rules were proposed for notation and for the order of the ab-sorbing systems. The collection of data was certainly useful in utilizing ultraviolet andvisible absorption spectra, but it included only a table for identifying absorption maximafrom absorbing systems and no table in which the absorbing systems could be found fromthe absorption maxima, which would be the most convenient method for structural identifi-cation.

This shortcoming has now been corrected, and the revised and enlarged version that hasbeen compiled for the present edition does contain a tabulation according to absorptionmaxima.

Table I is a list from which absorption maxima can be found from the absorbing systems,i.e., from the chemical structure. In general, the absorption of strongest intensity in arange of about 50my in wavelength was taken as the absorption maximum. Consequently, thedistance between two absorption maxima is usually more than 50my.

This table is used in the following manner. To look for the absorption maximum ofO' C~C' C~-C' C-C

cholesta-4,6-dien-3-one (I), we look under the absorbing system 'i *The order of the arrangement of absorbing systems is explained in detail under "Explanationof Notation and Arrangement." The desired absorbing system can be found directly fromTable I by following this order of arrangement, or the chromophore group in this absorb-ing system (O!C-C'.CC'.C in the above example) can be found from the "List of Chromophores"from which the compound number of (0:C)(C:C)2 is found as 772-831.

Table II is a reverse index of Table I. It is a list of absorbing systems to befound from the wavelengths of absorption maxima.

Ultraviolet and visible absorptions of organic compounds can be determined approxi-mately from the absorbing system, but the solvent used and measurement error must also betaken into account. Consequently, it is better to examine the wavelength regions aroundthe desired wavelength.

For example, if an unsaturated ketone having no substituent other than one ketogroup has an absorption maximum at 285my (loge 4.42) in ethanol, the following absorptionmaxima in a range of 2855my can be found from Table II.

(0:C)(C:C)

Examination of the absorbing system of these compounds from compound numbers in TableI shows that the (0:C)(C:C) group, and compounds 783, 827, and 828 in the (OrC)(CrC)2 groupare not the desired systems, because they have auxochromesjoined to the chromophore. The (OrC)(CrC)^ group has astronger absorption maximum at 393my (loge 4.8) and isnot the desired system. Further, compounds 793, 794, 795,797, and 799 of the (0:C)(CrC)2 group are dienal and aretherefore unsuitable. Consequently, the absorbing systemsthat remain are those which include compounds 804, 805, 806,

807, 808, 812, 813, and 815, i.e., a dienone of :9":C~~:C type, with two or three

alkyl auxochromes, or a trienone of type (VII) with a steric hindrance like compound 850.

These conclusions are based on the chemical observation that there is no hetero-atomin the molecule other than the oxygen atom in the keto group and on spectral observationsof the absorption maximum and intensity, but the possible absorbing systems can be furthernarrowed by comparing ultraviolet absorption curves.

Grateful acknowledgement is made to Dorothy U. Mizoguchi for her cooperation in pre-paring the manuscript.

Kenzo Hirayama

EXPLANATION ON NOTATION AND ARRANGEMENT

ABSORBING SYSTEMAn absorbing system consists of a chromophore or conjugated chromophores, printed in

bold face type in Table I, and an atom or atoms, if any, joined to the chromophore or con-jugated chromophores, and sometimes, consists merely of auxochromic atoms.

e.g. compound absorbing system notation

Rules determine the notation and sequence of absorbing systems, as mentioned below.

PRINCIPLE OF CITING AND ARRANGING ABSORBING SYSTEMSRule 1. The more predominant factor in an absorbing system is cited as early as

possible. Absorbing systems having a more predominant factor are placed later in thetables.

For example, C:C predominated over C:C as mentioned in Rule 3, and therefore thechromophore of butenyne is denoted such as CiC-CiC (not CiC-CiC), and CiC precedes CiCin the tables.

PREDOMINANCY OF ATOMS AND BONDSRule 2. The order of increasing predominancy of atoms or elements is as follows:H,C, and other atoms in the order of ascending group number of the Periodic Table

and increasing atomic number in the group.

Rule 3. The order of increasing predominancy of bonds is as follows:single bond < coordinate bond < double bond < triple bond

(An expression a < b indicates that b predominates over a.)

NOTATION OF UNIT CHROMOPHORE1. Aliphatic chromophores are denoted by atomic symbol and sign of unsaturated bonds.

e.g. CiC CiC CiCiC NiN N i N i N NiC NiC NiCiNPiP OiN OiCiC OiAs SiC SiCiS SiCiN SiCiO

Nitro and azoxy chromophores are denoted as QiN an respectively. Chromo-O O

phores of carboxylic acid (including ester), and its derivatives of type -CO-X such asamide, halide, and thiolic acid (including ester) are regarded as an unit chromophoreand denoted as:

OiC OiC OiC OiC6 ft 61 s

Chromophores of carbonic acid (including ester), and its derivatives such asH2N-CO-NH2, H2N-COOH, (HS)2CO, COCl2 are regarded also as an unit chromophore and denoted

as OiCO2, 0'.CN2, OiCON, OiCS2, OiCCI2.

2. Benzene chromophore is denoted by Arabic numeral 6, and carboaromatic condensedchromophores are denoted by Arabic numerals with or without subscript Arabic numerals,respectively indicating the number of atoms in each ring and the number of rings, citedin the decreasing order of the numerals denoting number of atoms.

e.g. naphthalene 66, azulene 75, indacene 655, anthracene and phenanthrene 63

3. Heteroaromatic chromophores are denoted by atomic symbol with or without sub-script Arabic numerals, respectively indicating the kind and number of the hetero-atom,and the notation of the corresponding carboaromatic chromophore.

e.g. thiophene S5, pyridine N6, indene N65, pyrimidine N26, purine N^ 65,thiazole SN5, benzothiazole SN65

4. Fulvenoid, quinonoid, and tropoquinonoid structures are denoted by symbols re-presenting the corresponding genuine aromatic chromophore, the exocyclic double bond(s),and the atom(s) joined to the exocyclic double bond(s).

e.g. methylenecyclopentadiene (fulvene) 5*.C, dihydropyridinone (pyridone) NGiO,pyranone (pyrone) 06.'O, tropone 7iO, methyleneindole N65iC, benzoquinone di-imine N'.6iN, naphthoquinone Oi66iO, dihydromethylenefuranone (methylene-

crotonolactone) 0.05.C, tropoquinone ^i 7!O

PREDOMINANCY OF UNIT CHROMOPHORERule 4. The predominancy of unit chromophores is determined by applying the follow-

ing criteria in series until-a decision is reached.

a) Heteroaromatic unit chromophores predominate over carboaromatic unit chromo-phores, which predominate over aliphatic unit chromophores.

e.g. CiC < 66 < N6

b) The predominancy of heteroaromatic unit chromophores is determined first byhetero-atoms contained in the ring, from the point of (i) the predominancy of the mostpredominant hetero-atom and, if there is a choice, of the subsequent predominant hetero-atom(s), (ii) a larger total number of hetero-atoms, and (iii) a larger total number ofthe most predominant hetero-atom and, if there is a choice, the subsequent predominanthetero-atom(s).

Examples for (i) : N6iS < 05, N665 < 065 < S5, 06 < ON5, ON5 < OP5for (ii): SN65 < SN265for (iii): SN265 < S2NSS, SeSN2665 < SeS2^ eS

c) The most predominant is that containing a larger total number of rings.e.g. 6 < 75 < 63, SN5 < SN65, Oi6iO < 66

d) The most predominant is that containing a larger ring.e.g. 5iO < 6 < 7iO, 55 < 65iO < 66 < 75 < 76iO, N5 < N6 < N7iO

e) The predominancy increases with the sequence of genuine aromatic, fulvenoid,quinonoid, and tropoquinonoid structures.

e.g. 6 < 0.6.0, 7iO < i7iO, N6 < N6iO < OiN6iO

f) The predominancy of aliphatic unit chromophores is determined first by compo-nental atoms, from the point of (i) the predominancy of the most predominant componentalatom and, if there is a choice, of the subsequent predominant componental atoms(s), (ii)a larger total number of componental atoms joined with unsaturated bond(s), and (iii) alarger total number of the most predominant componental atom and, if there is a choice,of the subsequent predominant componental atom(s).

Examples for (i) : CiC < NiN < NX < OiC < OiN < OiCiN < OiAsfor (ii): CiC < CiCiC, OiC < OiCiC, OiC < OiCiO, NiC < NiCiNfor (iii): NiCiC < NiCiN

g) The most predominant is that containing a more predominant bond.e.g. CiC < CiC, NiC < NiC

h) The more predominant is that containing a larger total number of a more pre-dominant componental atom(s) joined with coordinate bond(s) or a single bond(s) to theatom joined with unsaturated bond(s) and, if there is a choice, the subsequent predomi-nant componental atom(s) similarly joined.

e.g. OiC < OiC < OiCN2 < OiC < OiCON < OiC < OiCS2 < OiCSO < OiC < OiCCI2,

OiN < OiN, NiN < NiNA O

NOTATION OF CONJUGATED CHROMOPHORESConjugated chromophores are denoted by the notation of componental unit chromophores

joined by a hyphen.e.g. CiC-CiC, OiC-CiC-CiO, OiC-66-CiC, Q*.>N66-CiO

When there is a choice, the direction is so chosen as to make the most predominantchromophore and, if there is a choice, the subsequent predominant chromophore(s) comeas early as possible.

N * r*e.g. CiC-CiC, OiC-6

ing criteria in series until a decision is reached.

a) The predominancy is determined first by the most predominant unit chromophoreand, if there is a choice, the subsequent predominant unit chromophore(s), contained inthe absorbing system, from the point of (i) being predominant, (ii) being larger in totalnumber, and (iii) being cited earlier.

Examples for (i) : CiC-CiC-CiC < CiC-CiC < CiC-CiC < NiC-CiC-CiC < 6 < S-C.O 65;o) 6068

Part 37. (N25)-, (N2SrX)-,(X:N25:X)-, andY (v;N25:X)-ChromophoresA '.

(N25) 6069-6070(N25)(0:C) 6071(N25)(6) 6072-6080(N25)(6)3 6081(N25)(6)4 6082(N25)(6)(0:C) 6083(N25)(6)(0:(j:) 6084(N25)(6)(0:C) 6085

(!)(N25) (6) (O :N) 6086-6091

6(N25:C)(6)4(0:C)2

6092-6093(N25:0)(6) 6094-6095(N25:0)(6)(0:N) 6096(0:N25:C) 6097-6099(0:N25:C) (6) 6100-6105(;N25rC)(6) 6106-6123

(SrN25;)(6) 6124-6129

Part 38. (N2G)-, (N26:X)-,& (X:N26:X)-Chromophores(N26) 6130-6361(N26) (N:N:N)2 6362-6365(N26)(N:C) 6366(N26) (NrC) 6367-6369(N26)(0:C) 6370-6372

6(N26) (Or(^ )2 6373

O(N26)(6) 6374-6384(N26)(6)(C:C) 6385(N26)(6)(C:C)2 6386(N26)(6)(C:C)3 6387(N26)(6)(C:C)4 6388(N26) (6) (CrC)5 6389(N26)(6)(C:C)6 6390(N26) (6) (CrC)7 6391(N26)(6)(NrN) 6392(N26) (6) (NrNrN)2 6393

chromophore no .

(N26) (6) (OrN) (NrC) 63946

(N26rO) 6395-6513(N26rO)(6) 6514-6526(N26rO)(6)2 6527(N26rO)(6)(NrN) 6528(N26rO)(6)(NrC) 6529(N26rO)(6)(OrN) 6530-6534

(N26rS) 6535-6564(OrN26rO) 6565-6600(OrN26rO) (OrC) 6601-6603

A(OrN26rO) (OrN) 6604-6606

6(OrN26rO)(6) 6607(SrN26rO) 6608-6623(SrN26rS) 6624-6629

Part 39. Other N2-aromaticChromophores

(N265) 6630-6645(N265) (NrC) 6646-6648(N265)(OrC) 6649-6651

6(N265)(OrN) 6652-6657

(OrN265rO) 6658(OrN265rO)(OrC) 6659

6(N266) 6660-6691(N266) (OrC)2 6692

6(N266)(OrN) 6693-6705

O(N266)(6) 6706-6707(N266)(6)2 6708(N266)(6)(CrC) 6709(N266) (6) (CrC)2 6710(N266) (6) (CrC)3 6711(N266)(6)2(CrC)2 6712(N266)(6)2(CrC)4 6713(N266)(6)2(CrC)6 6714(N266rO) 6715-6740(N266rO)(OrC) 6741-6742

6(N266 rO) (O rN) 6743-6754

O(N266rO)(6)(OrN)

O 6755-6758(OrN266rO) 6759-6760(OrN266rN) 6761(N275) 6762(N275)(6) 6763-6764(N2665) 6765-6787

chromophore no .

(N2665rO) 6788(N263) 6789-6822(N263)(OrC) 6823-6824

N(N263)(OrC) 6825-6826

6(N263)(6) 6827-6828(N263rO) 6829(N2635) 6830-6841(N264) 6842-6849(N264)(6) 6850(N264rO) 6851(N26352) 6852-6853(N265) 6854(N266) 6855(N26552) 6856

Part 40. Ns-Aromatic Chro-mophores

(N35) 6857-6859(N35)2 6860(N35)(OrC) 6861(N35)(6) 6862-6882(N35)(6)2 6883-6891(N35)(6)3 6892-6893(N35)(6)2(CrC) 6894(N35) (N6) 6895-6898(N35rO)(6) 6899(N36) 6900-6938(N36) (CrC) 6939(N36)(OrC) 6940

A(N36)(OrC) 6941-6942

O(N36)(6) 6943-6945(N36rO) 6946('N36rO)(6)3 6947(N365) 6948-6979(N365)(OrC) 6980(N365)(OrN) 6981-7002

6(N365)(6) 7003-7006(OrN365rO) 7007-7008(N366rO) 7009-7010(OrN366rO) 7011(N3665) 7012(N363)(OrC) 7013

O(N3635) 7014(N364) 7015

Part 41. N^-Aromatic Chro-mophores

(N45) 7016-7030

chromophore no .

(N45)(N:N) 7031-7035(N45)(6) 7036-7045(N45)(6)(OrN) 7046-7047

O(N4SrN) 7048-7053(N465) 7054-7170(N465)(6) 7171-7177(N465:0) 7178-7247(N465:0)(6) 7248(0:N465:0) 7249-7291(;N465rO) 7292-7305(N466) 7306-7315(N466:0) 7316-7320(N466:0)(0:C) 7321-7328

6(0:N466:0) 7329-7336(0:N466:0)(0:C) 7337-7341

(0:N466:0)(6) 7342(;N466rO) 7343-7346

(-N466rO)(OrC) 7347

(;N466;) 7348-7352(N4665) 7353-7356(0:N463:0) 7357-7360(N4635) 7361-7362(N4635)(6) 7363-7367(N4635)(6)(0:C) 7368

O(N465) 7369-7370

Part 42. Other aromaticChromophores withN Hetero-atoms

(N565) 7371-7379(N565)(6) 7380-7382(N565)(6)(0r(p 7383

(N565:0) 7384-7389(N565:0)(6) 7390(N565:0)(6)(0:C) 7391

ti(N565:0)(6)(0:C) 7392

O(0:N565:0) 7393-7395(N565) 7396-7397

Part 43. Aromatic Chromo-phores with P or AsHetero-atom(s)

(0:P665:0) 7398(0:As665:0) 7399

chromophore no.

Part 44. (05)- & (X:05:X)-Chromophores

(05) 7400-7410(05)(C:C) 7411-7413(05) (NrC) 7414-7423(05)2(N:C)2 7424-7426(05) (N:C) (C:C) 7427-7430(05)2(N:C)2(C:C)2 7431(05)2(N:C)2(C:C)4 7432(05)2(N:C)2(C:C)6 7433(05) (6) (NrC) (CrC) 7434(05)(0:C) 7435-7439(05) (OrC)2 7440(05)2(0:C)2 7441(05)(0:C)(C:C) 7442-7444(05) (OrC)(CrC)2 7445-7446(05) (OrC) (CrC)3 7447-7448(05)(0:C)(C:C)4 7449(05) (OrC) (CrC)5 7450(05) (OrC) (CrC)6 7451(05)2(OrC) (CrC) 7452(OS)2(OrC)(CrC)4 7453(05)2(OrC) (CrC)6 7454(OS)2(OrC)2(CrC)2 7455(OS)2(OrC)2(CrC)4 7456(05)2(OrC)2(CrC)6 7457(05) (Or(J:) 7458-7460

N(05) (OrC) 7461-7472

6(05) (OrC)2 7473-7476

O(05) (OrC) (CrC) 7477-7484

6(05) (OrC) (CrC)2 7485-7487

6(05) (OrC) (CrC)3 7488-7489

O(05)(0:C)2(C:C)2

O 7490-7491(05) (OrN) 7492-7495

O(05) (OrN)2 7496

O(05) (OrN) (CrC) 7497

(05) (OrN) (NrC) 7498-7506

(05) (O rN) (OrC) 7507-7508O

(05) (OrN) (OrC) 7509-7511

(05) (6) 7512(05)(6)2 7513-7524(05)(6)3 7525-7529

chromophore no .

(05) (6)4 7530-7542(05) (6) (NrC) (CrC)

7543-7544(05)(6)3(OrC) 7545-7546(05)(6)4(OrC)2 7547(05) (6) (OrC) (CrC)

7548-7549(05)(6)2(OrC) 7550-7551

6(05)(6)3(OrC)(OrC) 7552

6(05) (N26) (NrNrN) 7553(05)(OrN26rO) 7554(Or05rC)(6)2 7555-7562(Or05rO)(6)3 7563(Or05rO)(66)(6) 7564

Part 45. (06)- and (06:X)-Chromophores

(06)(6)3 7565-7581(06)(6)3(CrC) 7582-7585(06) (6)3(CrC)2 7586-7587(06)(6)4(CrC) 7588-7590(06rO) 7591-7606(06rO)(OrC) 7607-7610(06rO)(OrC) 7611-7620

6(06.-O)(OrC)2 7621-7622

6(06rO)(6)2 7623

Part 46. Other aromaticChromophores withO Hetero-atom(s)

(065) 7624-7629(065) (OrC) 7630

A(065) (6)2 7631-7632(065) (6)4 7633-7634(Or065rC)(6) 7635-7641(066) (6) 7642-7670(066rO) 7671-7679(066rO)(OrC) 7680-7683

6(066rO)(6) 7684-7745(066rS)(OrC) 7746

A(0665) 7747-7759(0665)(Or05rC)(6) 7760(Or0665rO) 7761-7762(063)(6)(0r9) 7763-7765

O(063rC)(6) 7766-7767(063rO) 7768-7774

chromophore no .

(063:0)(0:C) 7775-7776

(063:0)(6) 7777(063:0) (6) (0:C) 7778

(063:65;) 7779(063:N65) 7780(063:N665) 7781-778206-}: :0( o:N26:0>' 7783(0635) 7784(064) 7785(0645) 7786(065) 7787

Part 47. Aromatic Chromo-phores with O andN Hetero-atoms

(ON5)(0:C) 7788-7791(ON5)(6) 7792(ON5)(6)2 7793-7794(ON5:C)(N66) 7795(0:ON5:C)(6) 7796(0:ON5:C)(6)2 7797-7843(0:ON5:C)(6)2(C:C)2

7844-7845(0:ON5:C)(6)2(0:N)

7846-7886(0:ON5:C)(6)2(0:N)2

67887-7895

(0:ON5:C)(05)(6)7896-7897

(0:ON5:C)(05)(6)(C:C)7898

(ON65) 7899-7902(ON65)(0:N) 7903-7908

(ON65)(6) 7909-7921(ON65) (6) (0:N) 7922-7927

(ON65)(6)(0:N)2 7928-7929

(ON65:C)(N66) 7930(ON65:C)(ON65)(C:C)

7931-7934(ON65:C)(ON65)(6)2(C:C)

7935-7936(ON65.-0) 7937(ON66:0) 7938(ON63:N) 7939-7940(ON64:N) 7941(ON25:0) 7942

chromophore no .

(ON25:0)(6) 7943(ON25:0)(6)2 7944(ON265) 7945(ON265:0) 7946(ON265:0)(6) 7947-7948(ON2665) 7949-7950(ON365)(6) 7951-7952

Part 48. Aromatic Chromo-phores with SHetero-atom(s)

(S5) 7953-7976(SS)2 7977-7978(SS)3 7979-7982(S5)4 7983-7984(SS)5 7985(SS)(CiC) 7986-7988(SS)(CrC)2 7989(SS)(NiC) 7990(S5)2(N:C)2 7991(SS)(N-C) 7992(SS) (N-C)(CrC) 7993(SS) (0:C) 7994-8002(S5)(0:C)(C:C) 8003(SS)2(OiC) (C:C) 8004(SS) (O 19) 8005-8009

(SS)(OrC)2 8010-8021

(SS) (OrC) (CrC) 8022-8024

(SS)(OrN) 8025-8026

(SS)(OrN)2 8027-8029O

(SS) (OrN) (CrC) 8030-8031

(SS) (6) 8032-8040(SS) (6)2 8041-8043(SS) (6) 4 8044(SS) (6) (NrC) 8045(S5)2(6)2(N:C)2 8046(SS) (6) (OrC) 8047-8049(S5)(6)2(0:C) 8050(SS) (6) (OrC) (CrC)

8051-8052(SS) (6) (Or^) 8053

(SS) (N6)4 8054(SS) (N4S) 8055-8060(S5)(05)(0:C)(C:C)

8061-8062(SS) (OrOSrC) (6) 8063(S5)(0:ON5:C) 8064(SS) (0:ON5 rC) (6)8065-8073

chromophore no .

(S6)(6)2 8074-8075(S6)(6)3 8076-8086(S6)(6)3(CrC) 8087-8090(S6) (6)3(C:C)2 8091-8092(S6)(6)4(C:C) 8093(S6)(6)4(C:C)2 8094(S6rC) (06) (6)4 8095-8096(S6rC) (S6) (6)4 8097-8098(S6rC)(S6)(6)4(CrC)

8099-8100(S6.-0) 8101(S65) 8102-8108(86S)(NrC) 8109(86S)(OrC) 8110-8111

(865) (6) (NrC) 8112(S65)(0:ON5:C)(6) 8113(0:865:0) 8114-8115(0:S65:C) (S65) 8116-8126(0:S65:S65:0) 8127-8131(S66:0)(0:C) 8132

(S665) 8133-8138(S665)(0:C) 8139-8140

(S665)(0:N) 8141-8152

(S63:N65) 8153(S63:N665) 8154(S63;N26;) 8155(S635) 8156-8158(S255) 8159

Part 49. Aromatic Chromo-phores with S andN Hetero-atoms

(SN5) 8160-8183(SNS)(OrC) 8184-8189

(SNS)(OrC)2 8190-8193

(SN5)2(6)4 8194-8195(SN5)2(6)8 8196-8197(SNS) (6) (CrC) 8198-8199(SN5) (6)

2 (C r C) 8200-8202(SN5:C) (N:6:C) 8203-8204(SNSrC) (NSrC) (6)8205-8206(SN5:C)(N6) 8207(SN5:C)(N66) 8208-8209(SN5:C)(N63) 8210(SN5:C)(ON65)(C:C)

8211-8214(SN5:C)(SN5)(6)4(C:C)

8215-8217

chromophore no.

(SN5:N) 8218-8219(SN5:0) 8220-8223(SN5:0)(6)(C:C) 8224-8225(SN5rO)(6)2(C:C)

8226-8227(SN5:S) 8228(SN5:S)(6)(C:C) 8229(SN5:S)(6)2(C:C) 8230(0:SN5:C)(6) 8231

(jSN5rC)(6) 8232-8233

(OrSN5.'c)(6) 8234-8235

(SrSN5.:)(6) 8236-8237I Li

(SrSN5|)(66) 8238(SrSN5:)(S5) 8239-8245

LI

(SrSN5*;)(S65) 8246 LI

(S : SN5 : ) (SN5 : C) 8247-8248 LI

(SN65) 8249-8275(SN65)(0:N) 8276-8279

6(SN65) (6) 8280-8285(SN65)(6)(C:C) 8286(SN65) (6) (0:N) 8287-8290

4(SN65:C)(N:C) 8291(SN65:C) (NrC)(CrC)

8292-8293(SN65rC) (NrC) (CrC)2 8294(SN65rC)(6)(NrC)

8295-8297

chromophore no .

(SN65rC) (6) (NrC) (CrC)8298-8300

(SN65rC) (6) (NrC)(CrC)28301-8303

(SN65rC) (6) (OrC) (NrC)8304

(SN65rC) (6)(OrC)(NrC) (CrC)8305

(SN65rC)(6)(0 .-C)(NrC)(Cr C)28306

(SN65rC)(Nr6rC) 8307-8308(SN65 rC) (N66) 8309-8310(SN65rC)(N66) (CrC) 8311(SN65rC)(ON65)(6)(CrC)

8312-8313

(SN65rC)(;SN5rS65rO)L r8314-8317

(SN65rC) (SN65) 8318-8319(SN65rC)(SN65) (CrC)

8320-8329(SN65:C)(SN65) (CrC)2

8330-8331(SN65rC)(SN65) (CrC)3 8332(SN65rN) 8333-8336(SN65rN)(OrC) 8337(SN65rN)(6) 8338(SN65rO) 8339(SN65rS) 8340-8347(SN665) 8348-8352(SN665) (6) 8353(SN665rC) (N66) 8354-8357(SN665rC)(SN65) (CrC)

8358-8360(SN665rC)(SN665) (CrC)

8361-8366(SN63rN) 8367-8373

chromophore no .

(SN63rO) 8374-8377(SN63 rC) (N66) 8378-8379(SN635rC) (SN635) (CrC)

8380(SN25) 8381-8385(SN25)(6) 8386-8387(SN25rN) 8389-8390(SN25rN)(6) 8391-8393(SN2665) 8396-8398(OrSN2665rC)(6) 8394-8395(SN26655) 8399-8401(S2N26655) 8402

Part 50. Other heteroaroma-tic Chromophores

(S06) 8403(0:80655:0) 8404(Se5)(6)2 8405-8407(Se5)(6)2(OrC) 8408(Se665) 8409-8415(Se665)(OrN) 8416-8419

6(SeN5rC)(N66) 8420(SeN5:C)(SN65) (CrC)

8421-8423(SeN65) 8424(SeN65rC)(N66) 8425(SeN65rC)(ON65)(6)(CrC)

8426-8427(SeN65rC)(SeN65) (CrC)

8428-8432(SeN65rO) 8433-8435(SeN65rS) 8436-8438(SeN265) 8439(SeN265)(6) 8440(SeN265)(6)2 8441(SeSN26655) 8442-8443

PART 1 . NO CHROMOPHORE

system

C

C-C

B-C

N-C

0-C

0-0-C

S-S

S-C

S-S-C

^O

s

system

Cl-N-C

Cl-As-C

Cl-O

Cl-S

Cl-S-S

Cl-S-O

Br-C

I-C

I-C-F

I-C-C1

Cli-c

system

I-C-Br

compound

1 , 2-dichloro-l , 1 , 2-trif luoro-2-iodo-e thane

tribromoiodome thane

solv. max. loge ref. no.

L 283 2.5 H16 53

L 346 2.5 H16 54

PART 2. (CrC)-CHROMOPHORES

system

c.c

c-c:c

c-c : c-c

c2~c:c

c2-c:c-c

c2~c:c-c2

N-CiC-C

0-CiC

oc-cicS-CiC

s-cic-c

S-CiC-C2

compound

ethylene

2-propen-l-ol; allyl alcohol

3-octene

5a-cholest-2-ene

5a-cholest-6-ene-33,5-diol

5a-cholest-ll-ene-3a,24-diol

2-methylpropene; isobutene

2-methyl-2-butene

5a-cholest-4-ene

cholest-5-en-33-ol; cholesterol

24-methyl-5a-cholest-7-ene; ergost-7-ene

methyl 5a-chol-9 (ll)-enate

24-methyl-5a-cholest-14-en-33-ol;ergost-14-en-33-ol

5a-cholest-8-ene

5a-cholest-8(14)-en-33-ol

1-piperidino-l-butene

vinyl ether

vinyl acetate

2-ethoxypropene

methylthioethylene

vinyl sulfide

ethyl vinyl sulfone

2 , 3-dihydrothiophene

2,3-dihydrothiophene 1-dioxide

2 ,3-dihydro-4-methylthiophene 1-dioxide

s o Iv. max. loge ref. no.

V 175 4.0 P39 55

H M.89 3.9 L33 56

H 185 3.9 P22 57

203 2.8 B72 58

204 3.1 B72 59

203 3.4 B72 60

vL84 4.0 S61 61

H 234 2.8 L33 62

203 3.6 B72 63

203 3.5 B72 64

207 3.6 B72 65

206 3.5 B72 66

204 3.6 H72 67

208 3.7 B72 68

208 4.0 B72 69

H 228 4.0 B98 70

204 4.2 H8n 71

no C63u 72

no S43c 73

225 4.2 P40 74

A 255 3.8 M48 75275 3.7

A 2^1O 2.4 F8 76

no FlOg 77

no F6 78

no K47 79

system

ci-c:cCl-CiC-As

Cl-CX-S

Br 2-C!C-Br 2

c.c-c.c

c:9-c:cc-c:c-c:cc:n:c

c-c : c-c : c-c

c-c:c-c:cC

c-c:

system

c-c:^ :c

c2-c: c-c : c-c

c2-c: cnp: c

c2-c: c-c: c

c-c-.ff.c-c

C O ~"C . C~~C . C"~Co

c2-c: 0-9: c-cC

c2-c: c-c: c-c

compound

pregna-3 , 5 , 20-triene

androsta-4 , 6-diene-3 B, 17 3-diol

3a-acetoxy-5 |3-pregna-16 9 20-dien-ll-one

3 , 8-p-menthadiene

l-methyl-4- (1 , 5-dimethyl-2 , 4-hexadien-yl)cyclohexene; zingiberene

cholesta-2 , 4-diene

2 , 4-dimethyl-l , 3-pentadiene

3-methylenecholest-4-ene

7-methylenecholest-5-en-3 $-ol

l-methyl-2-vinylcyclohexene

l,l,3-triethoxy-2--methyl-4-(2,6,6-tri-me thy 1-2-cyclohexenylidene) butane

1 , 1 ! -bicyclohexene

5a-cholesta-7 514-dien-3-one

3-acetoxy-5a-cholesta-7 , 9 (11) -diene

2 , 5-dimethyl-2 , 4-hexadiene

3 , 8-dimethyl-l , 10-bis (2 , 2 , 6-tr imethyl-cyclohexylidene) -2 , 8-decadien-5-yne-4,7-diol

l-cyclohexylidene-2-(2-hydroxy cyclo-hexylidene) ethane

3B-hydroxy-53-carda-14,16-dienolide;dianhydrodihydrogitoxigenin

1,3-p-menthadiene; a-terpinene

24-methylcholesta-5 , 7 , 22-trien-3-ol ;ergosterol

abietic acid

33,7,203-trihydroxy-5a-pregna-8(14),15-diene

53-cholesta-6,8-dien-33-ol

solv. max. loge ref. no.

A 235 4.4 H26 106

A 240 4.4 N6 107

A 238 4.2 S7 108

A 235 4.0 B93 109

A 235.5 3.7 B93 110

A 275 3.8 B60 111

A 232 3.9 L31 112

cH 239 4.2 M66 113

A 236 4.3 B25 114

A 233 3.9 B93 115

PE 235 112 116

236 B93 117

A 242 4.0 F30 118

A 243 4.2 F20 119

A 241 4.4 B121n 120

M 250 4.6 14 121

A 248 4.5 H8u 122

262 3.9 T14 123

A 262 3.6 B93 124

A 282 4.1 H82 125

A 237.5 4.2 K54 126

A 247 3.9 L9 127

E 275 3.7 B36 128

system

c2-c: CHp: C-C2C

C2-C .-9-9: c-c

N-C : c-c : cc:9-9:c-cO C

c-c .-9-9: c-c2

o-c: CH:: C-C2C

oc-c : c-c: C-C2

oc-c .'cnp: c-c

oc-

c:fToc-c .'9-9: c-c

s c-c: CH^ : c-cC

compound

24-methyl-5a-choles ta-6 , 8 (14) , 22-trien-33-ol; ergosta-6,8(14) ,22-trien-33-ol

24-methyl-3 , 5-cyclocholesta-6 , 8 (14) , 22-triene; 3,5-cycloergosta-6,8(14) ,22-triene

63-acetoxy-5-methyl-19-nor-5(3-cholesta-9 , ll-dien-6-one

(2,6, 6-trimethyl-l , 3-cyclohexadienyl) -acetaldehyde

9(ll),12(23)-dehydronor-56-choladiene

5 3-choles ta-8 , 14-dien-3 j3-ol ;cholestadienol-B^

21-acetoxy-17a-hydroxy-8 (14) , 9 (11) -pregnadien-3 , 20-dione

1- (diethylamino) -1 , 3-butadiene

3$,20-diacetoxy-5a-pregna-16,20-diene

2 , 4 (8) -p-menthadien-3-ol[enol form of pulegone]

2- (2-ethoxyvinyl) -1 , 3 , 3-trimethylcyclo-hexene

2- (2-acetoxyvinyl) -1,3, 3-trimethylcyclo-hexene

5H-6 ,7,8, 8a-tetrahydro-2 ,5,5, 8a-tetra-methylchromene

3-ethoxy-3 , 5-androstadien-17-one

3-acetoxy-3 , 5-cholestadiene

3 , 8-p-menthadien-3-ol[enol form of isopulegone]

ethyl 3-acetoxy-ll-carbethoxy-3 , 5-eusantonadienate

3a, 7-diacetyl-5 3 , 22a-spirosta-7 , 9 (11) -diene

3- (2-hydroxyethylthio) androsta-3 , 5-dien-17-one

3-benzylsulf inylandrosta-3 , 5-dien-17-one

solv. Vax. loge ref. no.

E 248 W37 129

A 261 4.4 F33 130

IP 248 4.4 E13n 131

PE 267 3.6 112 132

E 242 4.3 B161 133

A 250 4.3 F30 134

M 271 3.7 G23g 135

H 281 4.4 B98 136

A 2^39 4.2 M44 137

H 238 3.6 S7n 138

PE 222 112 139

PE 232 112 140

A 286 3.9 B151 141

A 241 4.3 D32 142

C 238 4.2 W13 143

H 236 3.1 S7n 144

A 238-9 4.4 A2 145

A 242 4.2 R34 146

A 268 4.4 R33 147

A 258 4.4 R29 148

system

c.c-c.cCl

cic-c : c-c:c-cC

cic-c ic C : c-cicci2-c:c c:c-ci2BrC-C !CHp: C-C

C

"^fe

c.c-cic-cicc-c : c-c : c-c : c-c

c-c:c-c:9-c:c

c-c :c-9: c-c:c-c

c-c : c-c : c-c:c-cC C

c-c .'9-9.' c-Ci c-c

C2-C i c-c ic~9i c-cC

C2-C i C-C i9~C. C-CC

C2-Ci c-ci 9~cicC2-Ci c-c '.9-9! c-c

C2-C .'9-cic-9: c-cC C

compound

2-chloro-l , 3-butadiene ; chloroprene

3-chloroandrosta-3,5-dien-17-one

perchloro-1 , 3-cyclopentadiene

per chloro-1 , 3-butadiene

3-bromocholesta-3 , 5-dien-17-one

3-acetoxyergosta-6,8(14) ,9(ll)-triene

3,5-cycloergosta-6,8(14) ,9(11) ,22-tetraene

1,3, 5-hexatriene

2,4,6-octatriene

1,3, 5-cyclooctatriene

1- (l-hydroxy-2 , 2 , 6-trimethylcyclohexyl) -3 , 7-dimethyl-4 , 6 , 8-nonatrien-l-yn-3-ol

8- (l-hydroxy-2 , 2 , 6-trimethylcyclohexyl) -6-methyl-3 , 5 , 7-octatr ien-2-ol

3,7, 7-tr imethy 1-1 , 3 , 5-cycloheptatriene

22-isospirostatriene

5a-choles ta-6 , 8 , ll-trien-3-ol

2,3,7, 7-tetramethyl-l , 3 , 5-cyclohepta-triene

4 , 8-dimethyl-10- (2 , 6 , 6-trimethyl-l , 3-cyclohexadienyl) -4,6, 8-decatrien-l-yn-3-ol

choles ta-3 , 5 , 7-triene

ergocalciferol; calciferol; vitamin D2

3-methyl-5- (2 , 6 , 6-trimethyl-2-cyclo-hexenylidene) -3-penten-l-ol

24-methylcholesta-5 ,7,14, 22-tetraen-3$-ol ; ergos ta-5 ,7,14, 22-tetraen-33-ol

andros ta-5 ,7,9(11) -triene-33 , 173-diol

3-hydroxy-24-methyl-9 , 10-secocholesta-5(10) ,6,8,22-tetraene

solv. max. logs ref. no.

H 223 4.1 B98 149

E 238 4.4 D7 150

A 323 3.2 MIg 151

A 224 4.2 R27 152

E 238 4.4 D7 153

E 232.5 4.3 F29 154287.5 3.8

iO 244 4.2 N4 155295 4.1

cH 257.5 4.9 W46x 156

iO 270 4.3 W3 157

265 3.6 C96 158

H 270 4.6 A41 159

H 274 4.5 A41 160

268 3.6 C98 161

A 306 4.3 R28 162

325 Z5 163

275 3.7 C98 164

PE 284 4.7 111 165

iP 315 4.2 S28 166

A 265 4.3 R4n 167

M 284 4.4 14 168

A 319 4.2 B37 169

iO 324 4.0 N5 170

E 280 4.4 K47g 171

system

c-c : c-c : c-c:c-cC C

c-c : c-c : c-c:c-c

O-Ci C-Ci C-Ci C-C

0-CiC-CiC-CiC-C2C C

oc-c ic-9*. c-ci C-C2SC-CiC-CiC-CiC-C2

ci*-

c:torrci2C C'l:: >cic-cic-c2CiC-CiC-CiC-CiC

C-CiC-CiC-CiC-CiC-C

C-CiC-CiC-CiC-CiC-CC C

C-CiC-CiC-CiC-CiC-C

C2-C i C-C iCHpi C-Ci C-C

c-

c:r:n:

system

oc-c : c~c : c-c : c-Cic-c

QiC-CiC-CiC-CiQC-Q : c-c : c-c : c-c .9c-Cic-cic-c.c-Cidci-p : c-c : c-c : c-c .9Br-Q : c-c : c-c : c-c .9(c:5

(CiC)5-C2

(CiC)5-C4

(CiC)5-C5

(CiO5-C6

(CiC)6-C2

(CiC)6-C4

(CiC)6-C5

(CiO6-C6

(CiC)7

(CiC)7-C6

(CiC)8-C6

(CiC)9-C2

compound

1- (4-acetoxy-3-methyl-l , 3-butadienyl) -2,6, 6-trimethyl-l , 3-cyclohexadiene

3-acetoxy-24-methylcholesta-3,5,7,9(11) ,22-pentaene [enol acetateof ergosta-4,7,9,22-tetraene]

cyclooctatetraene

methylcyclooctatetraene

1 , 2-dimethylcyclooctatetraene

chlorocyclooctatetraene

bromocyclooctatetraene

1,3,5,7, 9-decapentaene

2,4,6,8, 10-dodecapentaene

3-methyl-l- (2,6, 6-trimethyl-l-cyclo-hexenyl) -1,3,5, 7-octatetraene

3 , 7-dimethyl-l- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) -1,3,5, 7-octatetraene

retinol; vitamin A

2 , 4 , 6 , 8 , 10 , 12-tetradecahexaene

2 , 6 , 11 , 15-tetramethyl-3 ,5,7,9,11,13-hexadecahexaenedioic acid; dihydro-crocetin

3 , 7-dimethyl-9- (2 , 6 , 6-trimethyl-2-cyclo-hexenylidene) -1 ,3,5, 7-nonatetraene ;anhydrovitamin A-^

3 ,4-dehydroretinol; vitamin A2

1,3,5,7,9,11 , 13-tetradecaheptaene

aurochrome

f lavoxanthin

dihydro-3-carotenone

2 , 4 , 6 , 8 , 10 , 12 , 14 , 16 , 18-eicosanonaene

solv. max. loge ref. no.

PE 245 4.1 112 191312 4.2

A 356 4.2 H42 192

A 280 2.6 M43g 193

280 2.5 C93 194

no C93 195

no C91 196

no C91 197

iO 230 3.3 M26 198334 5.1

M 326 4.9 B88 199343 4.9

A 342 4.6 S16n 200

348 4.7 S16n 201

H 325 4.7 A41 202

C 360 D18 203

H 379 KIl 204

A 370 4.9 19 205

A 288 4.3 F4 206352 4.6

iO 390 4.6 M26 207

CD 428 KIl 208

B 430 K68 209458.5

B 436 K66 210

B 412 5.3 B88 211

system

(CiC)9-C6

(CiC)9-C7

(CiC)9-C8

(CiO10-C8

(CiC)11-C9

(CiO11-C10

(CiO12-C10

(CiC)13-C8

(CiO13-C10

(CiC)13-O2C3

(CiO14-C10

(CiC)15-C10

(CiC)15-C12

(CiC)19-C14

compound

5 , 6-dihydro-a-carotene

rubichrome

8-apo-3-carotenol; 3-apo-2-carotenol

cryptof lavin

dihydrobisanhydro-3-carotenone

a-carotene

y-carotene

3-carotene

4,4 f-dehydro-3-carotene; isocarotene

3,4-dehydro-3-carotene

decapreno-e^-carotene

3,4,3f , 4 T-bisdehydro-3-carotene

rhodoviolascin

anhydroeschscholzxanthin

3 , 4 , 3 T , 4 f -bisdehydrolycopene

decapreno- 3-carotene

dodecapreno- 3-carotene

solv. max. loge ref. no.

B 453.5 K13 212

CD 476 K14 213

A 456 V8 214

B 470 K12 215

B 460 K63 216

CD 475 5.0 02n 217507 5.0

PE 475 5.0 M31n 218

H 461 5.2 Z4n 219

PB 280 4.3 110 220465 5.1

H 308 4.5 Z2 221382 4.4471 5.2

PE 461 5.1 111 222

cH 246 4.4 K8 223321 4.8392 4.4505 5.2

H 333 4.3 Zl 224404 4.6490 5.2

B 511 K20 225

H 352 4.1 Zl 226499 5.0

B 531 KIl 227

cH 328 4.5 K6 228405 4.2509 5.1

cH 372 4.4 K7 229444 4.5547 4.9

PART 3. (CiC)-CHROMOPHORES AND CUMULENOID CHROMOPHORES

system

CiC

c-cic

C-CiC-C

CiC-CiC

C-CiC-CiC

C-CiC-CiC-C

CiC-CiC-CiC

C-CiC-CiC-CiC-C

C-CiC-CiC-CiC-CiC-C

(CiC)5-C2

(CiC)6-C2

(CiC)7-C2

c:c-c:c

cic-c:c-c

c;c-c:c-c2

Ci C-C. C-C, C

CiC-CiC-C2C

C-CiC-CiC

C-CiC-CiC-C

compound

acetylene

1-octyne

2-octyne

butadiyne

1 , 3-pentadiyne

3 , 5-octadiyne-2 , 7-diol

hexatriyne

2,4,6-octatriyne

2,4,6 ,8-decatetrayne

2,4,6,8, 10-dodecapentayne

2 , 4 , 6 , 8 , 10 , 12-tetradecahexayne

2,2,17,17-tetramethyl-3,5,7,9,ll,13,15-octadecaheptayne

butenyne; vinylacetylene

2-penten-4-yne

5-chloro-3-hexen-l-yne

5-bromo-3-hexen-l-yne

3-methyl-3-hexen-5-yne-2-ol

3-methyl-3-penten-l-yne

2-ethynyl-l , 3 , 3-trimethylcyclohexene

2 , 7-octadien-5-yn-4-ol

3-decen-5-yn-2-ol

l-bromo-2-nonen-4-yne

solv. max. loge ref. no.

V 173 3.8 B113 230

V 185 3.6 P21 231222.5 3.7

V 177.5 3.8 P21 232222.5 3.7

A 234 B86 233

A 236.5 2.6 A33 234

A 242.5 2.5 A35 235

A 284 B86 236

A 207 5.1 A35 237268 2.3286 2.3

A 234 5.4 A36 238306 2.3328 2.3

A 260.5 5.5 C84 239324.5 2.4

A 284 5.6 C84 240

E 310.5 5.7 B90 241357.5 2.8

V 213 4.0 B113 242

A 222 4.0 A34 243

A 226 4.1 H44 244

A 237 4.2 H44 245

A 224 4.1 J29 246

H 219 4.0 B98 247

H 227 4.1 A41 248

A 224 4.2 H41 249

A 226 4.2 H38 250

H 242 3.9 B122 251249 3.9

system

c-c;c-c:c

C-C: C-C : C-CC

C-CiC-CiC-C2

Si-Ci C-C: C-C

c:c-c:c-c:c

c-c:c-c:c-c:c

c-c : c-c c-c:c-c

c-c:c-c;c-c:cC

C-C .C-CiC-C .C-CC

c-c:

system

(CiC)(CiC)4-C6

(CiC)(C .'C)6-C8

(CiC)(CiC)10-C10(CiC)(CiC)11-C10

(CiC)(CiC)12-C10CiC-CiC-CiC

CiC-CiC-CiC-C

C-CiC-CiC-CiC-C

C-C -9-CiC-Ci C-Ci C-CC C

(CiC)2(CiC)4-C

(CiC)2(CiC)4-C6

(CiC)2(CiC)6-C4

CiC-CiC-CiC-CiC-C

C-CiC-[CiC]3-CiC-C

C-[CiC]3-[CiC]2-C

(CiC)3(CiC)3-C

(CiC)4(CiC)2-C2

(CiC)5(CiC)2-C2

(CiC)6(CiC)2-C2

CiCiC

compound

3 , 7-dimethyl-9- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) -2 , 4 , 6-nonatrien-8-yn-l-ol ;7,8-dehydrovitamin A

3 , 8-dimethyl-l , 10-bis (2,6, 6-trimethyl-1-cyclohexenyl) -1,3,7, 9-decatetraen-5-yne

15 , 15 r -dehydro- 3-carotene

3 , 4 : 15 , 15 T -bisdehydro- 3-carotene

3,4:3' ,4f :15,15f-trisdehydro-B-carotene

l-buten-3 , 5-diyne ; vinyldiacetylene

2-hepten-4 , 6-diyne

cis-8-decene-4,6-diynoic acid

trans-8-decene-4 ,6-diynoic acid

l,4-di(l-cyclohexenyl)butadiyne

1,3,9, ll-dodecatetraene-5 , 7-diyne

1 , 8-di (1-cyclohexenyl) -2 , 7-dimethyl-1 , 7-octadiene-3 , 5-diyne

1 , 12-di (1-cyclohexenyl) -1 ,3,9, ll-dodeca-tetraene-5 , 7-diyne

2-nonaene-4,6,8-triyneyl acetate

di (1-cyclohexenyl) hexatriyne

3,5-tridecadiene-7 ,9,11-triynoic acid;isomycomycin

2,10, 12-tridecatriene-4 , 6 , 8-triynylacetate

l,14-diacetoxy-2,12-tetradecadiene-4,6,8,10-tetrayne

2,2,17,17-tetramethyl-3,15-octadeca-diene-5 ,7,9,11 , 13-pentayne

1 , 18-diacetoxy-2 , 16-octadecadiene-4,6,8,10,12, 14-hexayne

allene

solv. max. loge ref. no.

H 252 4.3 A41 273328 4.5

M 357 4.7 14 274

PE 431 5.0 110 275

PE 439 5.0 111 276

PE 449 5.0 111 277

A 262 A19 278

A 264 4.1 A33 279

H 265.5 A19 280

H 265.5 A19 281

A 237 4.5 B86 282291 4.4

307 B91 283

E 313 4.3 B85 284

E 374 4.8 B85 285

M 245 5.0 B91 286309 4.2

A 254 4.8 B86 287330 4.4

E 267 5.0 C22x 288324 4.6

PE 274 4.8 B91 289342 4.6

M 275 5.0 B91 290364 4.1

M 297 5.2 B90 291398 4.2

M 316 5.2 B91 292

V 'XL 71 S81 293

system

c-c:c:c

c-c : c:c-c

O-C:C:C-NC2-CiCiC-CiCiC-C2

c2-c:c:9 CiCiC-C2Br Br

(c:c:c) (CiC)2(CiO2-C

C2-CiCiCiC-C2

C2-CiCiCiCiCiC-C2

C2-[Ci]9C-C2

compound

1,2-pentadiene; ethylallene

2 , 3-pentadiene ; 1 , 3-dimethylallene

1- (tert-butylamino) -3-hydroxyallene

1,4 -bis (2,2,6, 6-tetramethylcyclohexyl-idene) -1 , 3-butadiene

2 , 3-dibromo-l , 4-bis (2 , 2 , 6 , 6-tetramethyl-cyclohexylidene) -1 , 3-butadiene

3,5,7,8-tridecatetraene-10,12-dioicacid; mycomycin

1 , 2 -bis (2 ,2,6, 6-tetramethylcyclo-hexylidene) ethylene

1 , 4-bis (2 , 2,6, 6-tetramethylcyclo-hexylidene)butatriene

1 , 8-bis (2,2,6, 6-tetramethylcyclo-hexylidene) octaheptaene

solv. max. loge ref. no.

V 177 4.4 J29n 294181 4.4227 1.7

V 171 4.3 J29n 295

287 4.8 W32n 296

E 224 4.7 B92 297

E 231 4.7 B92 298

281 4.8 C63 299

E 230 4.0 B92 300271.5 4.5

E 238 5.2 B92 301339 4.5

PE 325 5.4 B92 302390 4.2465 4.2

PART 4. (N:N)-, (N:N)-, AND (N: NrN)-CHROMOPHORE6

system

C-NiN-C

C-N: N-C6

C-N:N:N

compound

azome thane

azopropane

azoxyme thane

azoxy tr if luorome thane

azoxycyclohexane

azidoethane

solv. \nax. loge ref. no.

W 344 1.0 M20 303

cH 362 1.0 M20 304

V 221 3.8 J8 305

V 211 3.9 J8 306303 1.2

A 223.5 3.9 L2n 307

A 222 2.2 S41n 308287 1.3

PART 5. (NiC)-CHROMOPHORES

system

NiC-C2

N: C-N2

N: C-NC

NiC-O2

NiC-OC

NiC-ON

NiC-SN

C-NiC-N

C-NiC-NC

compound

3-iminobutanonitrile; diacetonitrile

guanidine

acetylguanidine

nitroguanidine

l-amino-3-nitroguanidine

acetamidine

ethyl carbonimidate

ethyl acetimidate; ethyl a-iminoethylether

methyl carbamidoimidate; 0-methylisourea

methyl carbamidoimidothiolate; S-methylisothiourea

l-isopropyl-4 , 4-dimethyl-2-imidazoline

2-methyl-2-imidazoline

4 , 4-dimethyl-2-propyl-2-imidazoline

l-isopropyl-2 , 4 , 4-trimethyl-2-imidazoline

solv. max. loge ref. no.

H 259 4.3 S32 309

6.2 no K39 310

*1 262 1.3 S32 311

6.1 220 2.8 M18 312

10.5. 229 4.1 M18 313

3.0 265 4.1 L25 314

7.0 265 4.1 L25 315

10.0 265 4.1 L25 316

W 214 3.7 L25 317267 4.1

7.0 1.6 M18 318

13.0 219 3.0 M18 319

M 225 1.4 S32 320

M 254 1.1 S32 321

7.5

system

C-NiC-S2

N-NiC

N-NiC-C

N-NiC-C2

compound

2-cyanomethyl-l-isopropyl-4 , 4-dimethyl-2-imidazoline

2- (ethoxycarbony !methyl) -1-isopropyl-4 , 4-dimethy 1-2-imidazoline

methyl N-methylcarbimidodithiolate ;(methylimino)dimethylthiomethane

formaldehyde 2 , 4-dinitrophenylhydrazone

propionaldehyde 2 , 4-dinitrophenyl-hydrazone

(2 ,6,6-trimethyl-2-cyclohexenyl) form-aldehyde semicarbazone;a-cyclocitral semicarbazone

(2,6, 6-trimethyl-l-cyclohexenyl) acet-aldehyde phenylsemicarbazone;3-cyclocitral phenylsemicarbazone

acetaldehyde thiosemicarbazone

acetone m-nitrophenylhydrazone

acetone p-nitrophenylhydrazone

acetone 2 , 4-dinitrophenylhydrazone

solv. Vax. loge ref. no.

A 258 4.4 F16n 332

*1 231 3.8 F16n 333

A 222 3.8 F16n 334271 4.4

*1 231 3.9 F16n 335

cH 217 3.9 A13 336

A 225 4.3 B120 337256 4.1348 4.4

C 258 4.1 B120 338348 4.4

*2 264 J26 339430 4.3

A 228 4.2 B120 340256 4.1357 4.3

C 252 4.1 B120 341361 4.3

*2 272 J26 342438 4.4

A 232 4,2 H45 343

PE 248.5 4.9 112 344

A 229.5 3.8 E22 345270 4.9

M 268 4.4 B84 346

M 250 4.1 B84 347392 4.3

A 228 4.3 B120 348255 4.1362 4.3

*1 acidified A *2 0.2N NaOH /AH-C (9 :1)

system compound

cyclopentanone 2 , 4-dinitrophenyl-hydrazone

cyclohexanone 2,4-dinitrophenyl-hydrazone

5a-cholestan-3-one 2 , 4-dinitrophenyl-hydrazone

hydroxyacetone 2 , 4-dinitrophenyl-hydrazone

1 , 3-dihydroxyacetone 2 , 4-dinitrophenyl-hydrazone

1 , 1 f -diacetoxyacetone 2 , 4-dinitro-phenylhydrazone

1,1, 1-trif luoroacetone 2 , 4-dinitro-phenylhydrazone

chloroacetone 2 ,4-dinitrophenyl-hydrazone

1 , 3-dichloroacetone 2 , 4-dinitrophenyl-hydrazone

bromoacetone 2 , 4-dinitrophenylhydrazone

acetone N~methyl~2 , 4-dinitrophenyl-hydrazone

5a-cholestan-3-one N-methyl-2 , 4-dinitro-phenylhydrazone

acetone semicarbazone

2-ethoxycarbonyl-2-(3-ethoxycarbonyl-1-methylallyl) cyclopentanone semi-carbazone

cyclohexanone semicarbazone

methyl 12a-bromo-4-methoxy-3,ll-disemicarbazono-5 (3-cholanoate

solv. Vax. loge ref. no.

C 258 4.1 B120 349366 4.4

*1 431 4.3 J26 350

A 363 4.4 B120 351

C 367 4.4 B120 352

A 363 4.4 B120 353

C 366 4.4 B120 354

A 370 4.4 C62 355

C 255 4.0 R9 356354 4.4

C 359 4.3 R9 357

C 255 4.0 R9 358351 4.2

327 3.8 K33 359

340-4 3.9 K33 360

337 4.0 K33 361

344 4.1 K33 362

M 375 4.3 B84 363

C 245 4.0 D32 364

A 225.5 4.0 G12 365

A 232.5 4.2 H55 366

A 229.5 4.0 G12 367

M 230 4.1 M22 368

*1 0.2N NaOH/A+C(9:l)

system

O-N:C-Co-N:c-c2

c-c : NHM: c-c

C-N: c-c : N-C

C-N !9-9: N-C

N-N: C-C:N-NC

N-N: c-c : N-N

O-N:C-C:N-O

compound

5-hydroxy-5a-cholestan-6-one semi-carbazone

acetone thiosemicarbazone

cyclohexanone thiosemicarbazone

acetaldehyde oxime

acetone oxime

acetone 2,4-dinitrophenyloxime

dibutylidenehydrazine ; acetaldehydeazine

bis (cyclohexylimino) ethane ; glyoxalbiscyclohexylimide

2,3-bis (butylimino) butane; diacetyldisbutylimide

D-glucose phenylosazone

3a-acetoxy-12a-bromo-20 , 21-bis (2 , 4-dinitrophenylhydrazono)-ll-oxopregnane

2,3-dihydrazonobutane; diacetyl di-hydrazone; butanedione dihydrazone

3a-hydroxy-ll , 21-hydrazone-5 B-cholanoicacid

2 , 3-butanedione bis (2 , 4-dinitrophenyl-hydrazone)

1 , 2-cyclobutanedione bis (2 , 4-dinitro-phenylhydrazone)

1 , 2-cyclopentanedione bis (2 , 4-dinitro-phenylhydrazone)

1 , 2-cyclohexanedione bis (2 , 4-dinitro-phenylhydrazone)

butanedione disemicarbazone; diacetyldisemicarbazone

bis (hydroxyimino) ethane ; glyoxime

solv. max. loge ref. no.

A 228 4.1 RlO 369

A 228.5 3.9 E22 370271 4.3

A 229.5 3.9 E22 371272 4.4

no L23 372

W 190 3.7 B113 373

242 5.1 C106 374

A 205 4.1 B26 375

M 217 4.3 C12 376267 2.4

A 209 4.3 B26 377

A 253 4.2 G23x 378394 4.4

B 354 4.5 F35 379398 4.4

A 265 4.2 B27 380

301 W42 381

C 395 4.6 R4 382440 4.5

C 352 4.5 R4 383440 4.4450 4.4

352 4.5 R4 384403 4.4452 4.4

C 352 4.5 R4 385

281 B87 386

A 236 4.2 B26 387

system

0-NiC-ciN-o

O-N: C-C:N-N

NiC-NiC-N9ri 2

C-NiC-CiC-C

N-NiC-CiC

N-NiC-CiC-C

N-NiC-CiC-C2

compound

2,3-bis(hydroxyimino)butane; dimethyl-glyoxime

1 , 2-bis (hydroxyimino) cyclohexane ;1,2-cyclohexanedione dioxime

2-hydroxyimino-3-thiosemicarbazonobutane

amidinoguanidine; biguanide

l-butylimino-2-butene ; crotonaldehydebutylimide

acrylaldehyde 2 , 4-dinitrophenylhydrazone

acrylaldehyde semicarbazone

crotonaldehyde p-nitrophenylhydrazone

crotonaldehyde 2 , 4-dinitrophenyl-hydrazone

crotonaldehyde N-methyl-2 , 4-dinitro-phenylhydrazone

crotonaldehyde semicarbazone

3-methylcrotonaldehyde 2 , 4-dinitro-phenylhydrazone

solv. ^max. loge ref. no.

A 227 4.3 B26 388

alk ^ 26O S54 389

M 237 4.1 S2g 390

M 294 S2g 391

ntr 231 4.0 Gl 392

A 220 4.4 B26 393

A 228 4.2 B120 394241 4.2251 4.2366 4.4

C 256 4.0 B120 395367 4.4

*1 459 4.5 J26 396

A 264.5 4.3 L33 397

M 285 3.9 B84 398400 4.5

*2 273 B84 399523

A 244 4.3 B120 400256 4.3373 4.5

C 256 4.3 B120 401372 4.5

*1 452 4.5 J26 402

*2 273 B84 403523

M 260 4.2 B84 404397 4.3

264.5 4.4 H24 405

A 256 4.3 B120 406381 4.5

*1 0.2N NaOH/A+C(9:l) *2 10% KOH/A

system

N-N: c-c : c-cC

N-N: c-c: c-c2C

compound

(2,6, 6-trimethylcyclohexylidene) -acetaldehyde 2 , 4-dinitrophenyl-hydrazone

3-methylcrotonaldehyde semicarbazone

cyclohexylideneacetaldehyde semi-carbazone

(2,2, 6-trimethylcyclohexylidene) -acetaldehyde phenylsemicarbazone

3-methyl-4- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) crotonaldehyde m-nitrophenylhydrazone

3-methyl-4- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) crotonaldehyde p-nitrophenyl-hydrazone

2-methylcrotonaldehyde 2 , 4-dinitro-phenylhydrazone; tiglinaldehyde 2,4-dinitrophenylhydrazone

2-methyl-4- (2,6, 6-trimethyl-l-cyclo-hexenyl) crotonaldehyde N-methyl-2 , 4-dinitrophenylhydrazone

2-methylcrotonaldehyde semicarbazone ;tiglinaldehyde semicarbazone

l-p-menthen-7-al semicarbazone;phellandral semicarbazone

2-methyl-4- (2 , 6 , 6-trimethy 1-1-cyclo-hexenyl) crotonaldehyde phenylsemi-carbazone

2-methylcrotonaldehyde thiosemi-carbazone; tiglinaldehyde thiosemi-carbazone

2-f ormyl-1 , 3 , 3-tr imethylcyclohexene 2 , 4-dinitrophenylhydrazone ; 3-cyclocitral2 , 4-dinitrophenylhydrazone

solv. max. loge ref. no.

C 260 4.3 B120 407382 4.4

C 260 4.2 H47 408380 4.5

A 273 4.5 E22 409

A 274 4.5 D19 410

PE 241 4.3 112 411284.5 4.2

M 248 4.1 B84 412314 4.6

M 283 4.1 B84 413406 4.5

A 376 4.5 J26 414

*1 258 J26 415458 4.5

M 267 4.3 B84 416404 4.4

A 264 4.3 E22 417

A 265 4.4 C85 418

PE 236 4.3 112 419282 4.5

A 248 3.9 E22 420299.5 4.5

A 225 4.1 B120 421255 4.2387 4.4

C 257 4.2 B120 422389 4.4

*1 0.2N NaOH/A+C(9:l)

system

N-N: c-c:c-cC

K-N:?1:c

N-NiC-CiC-C2C

compound

2-f ormyl-1 , 3 , 3-tr imethylcyclohexenesemicarbazone; $-cyclocitral semi-carbazone

2-f ormyl-1 , 3 , 3-trimethylcyclohexenepheny Isemicarbazone ; (3-cyclocitralphenylsemicarbazone

4- (2 , 6 , 6-trimethyl-2-cyclohexenyl) -3-buten-2-one 2 , 4-dinitrophenylhydrazone ;ot-ionone 2 , 4-dinitrophenylhydrazone

4-cyclohexyl-2-cyclohexen-l-one 2 , 4-dinitrophenylhydrazone

5a-cholest-l-en-3-one 2 , 4-dinitro-phenylhydrazone

5a-cholest-l-en-3-one N-methyl-2 , 4-dinitrophenylhydrazone

3-hepten-2-one semicarbazone

4-cyclohexyl-2-cyclohexen-l-one semi-carbazone

5 3-cholest-l-en-3-one semicarbazone

3-hepten-2-one thiosemicarbazone

3-methyl-3-buten-2-one semicarbazone

4-methyl-3-penten-2-one 2 , 4-dinitro-phenylhydrazone; mesityl oxide2 , 4-dinitrophenylhydrazone

cholest-4-en-3-one 2 ,4-dinitrophenyl-hydrazone

4-methyl-3-penten-2-one semicarbazone ;mesityl oxide semicarbazone

solv. max. loge ref. no.

A 272 4.4 B156 423

A 236.5 4.3 B156 424280.5 4.4

A 223 4.2 B120 425245 4.3252 4.3377 4.4

C 256 4.4 B120 426389 4.4

C 382 4.4 W27 427

C 384 4.4 D28 428

C 248 4.3 D28 429393 4.3

A 264.5 4.4 E21 430

A 263.5 4.3 W27 431

A 270 4.0 15 432

A 246 4.0 E22 433301.5 4.6

A 259.5 4.3 E21 434

A 224 4.2 B120 435256 4.2379 4.4

C 255 4.3 B120 436389 4.4

*1 250 J26 437452 4.4

C 256 4.3 J33 438393 4.5

A 260 4.0 M27 439

*1 0.2N NaOH/A+C(9:l)

system

N-N: c-c : c-c

N-NiC-CiC-C2

compound

3-methyl-2-cyclohexen-l-one semi-carbazone

cholest-4-en-3-one semicarbazone

3-methyl-2-cyclohexen-l-one thiosemi-carbazone

3-methyl-3-penten-2-one 2 , 4-dinitro-phenylhydrazone

3(3-acetoxypregna-5 , 16-dien-20-one2 , 4-dinitrophenylhydrazone

1-acetylcyclohexene 2 , 4-dinitrophenyl-hydrazone

cholest-4-en-6-one 2 , 4-dinitrophenyl-hydrazone

2-ethy 1-2-cy clohexen-1-one 2 , 4-dinitro-phenylhydrazone

3-methyl-3-penten-2-one semicarbazone

3a-hydroxy-5$-pregn-16-en-20-one semi-carbazone

1-acetylcyclohexene semicarbazone

33-acetoxycholest-4-en-6-one semi-carbazone

2 -me thy 1-2-cy clohexen-1-one semi-carbazone

1-acetylcyclohexene thiosemicarbazone

3 , 4-dimethy l-3-penten-2-one 2 , 4-dinitro-phenylhydrazone

l-acetyl-2-methylcyclohexene2 , 4-dinitrophenylhydrazone

1,2,3,4,5,6,7, 8-octahydronaphthalen-1-one 2 ,4-dinitrophenylhydrazone

solv. max. loge ref. no.

A 265.5 4.4 E21 440

A 270.5 4.4 J33 441

C 271 4.4 J33 442

A 246.5 4.0 E22 443302.5 4.5

A 377 4.4 M27 444

C 384 4.4 K27 445

A 228 4.2 B120 446255 4.2377 4.4

C 253 4.3 B120 447387 4.4

C 377 4.4 RlO 448

C 385 4.4 J4 449

A 259.5 4.4 E21 450

C 267 4.4 D32 451

A 260.5 4.4 H45 452

A 258 4.0 RlO 453

A 264.5 4.3 E21 454

A 247 4.0 E22 455301 4.6

A 367 4.3 M27 456

A 365 4.4 W49 457

A 381 4.4 BlOl 458

C 259 4.2 W27 459387.5 4.4

system

O-N: c-c : c-cO-N: c-c:c-cO-N: 9-c:c-c2

C

O-N .'9-9: c-c

s;^ **^ ?

-":

-*|

compound

3 , 4-dimethyl-3-penten-2-one semi-carbazone

l-acetyl-2-methylcyclohexenesemicarbazone

4-isopropyl-2 , 3-dimethyl-2-cyclopenten-1-one semicarbazone

1,2,3,4,5,6,7, 8-octahydronaphthalen-1-one semicarbazone

crotonaldehyde oxime

2-f ormyl-5a-cholest-2-ene oxime

4-methyl-3-penten-2-one oxime; mesityloxide oxime

3-methyl-2-cyclopenten-l-one oxime

3-methyl-2-cyclohexen-l-one oxime

cholest-4-en-3-one oxime

3$-hydroxycholest-5-en-7-one oxime

3-methyl-3-penten-2-one oxime

1-acetylcyclohexene oxime

l(6)-p-menthen-2-one oxime; carvoneoxime

5-hydroxy-3-caren-2-one oxime;2-hydroxy-3-caren-5-one oxime

33-acetoxy-5a-cholesta-8,14-dien-7-one2 , 4-dinitrophenylhydrazone

cholesta-l,4-dien-3-one 2 ,4-dinitro-phenylhydrazone

cholesta-1 , 4-dien-3-one semicarbazone

2 , 6-dimethyl-2 , 5-heptadien-4-one 2 , 4-di-nitrophenylhydrazone; phorone 2, 4-di-nitrophenylhydrazone

4-benzoyloxy-2 , 4 , 6- t rime thy 1-2 , 5-cyclo-hexadien-1-one 2 , 4-dinitrophenyl-hydrazone

solv. max. loge ref. no.

A 240 4.4 M27 460

A 240 4.0 M27 461

A 267 4.4 G13 462

A 267 4.4 BlOl 463

A 229.5 4.2 E2 464

A 233 4.3 P30 465

W 236.5 4.1 E22 466

A 234 4.1 E22 467

A 236 4.1 E22 468

A 240 4.4 E22 469

E 238 4.2 E3 470

A 230.5 4.3 E22 471

A 231 4.1 G12 472

A 236 4.2 G12 473

237 4.1 C97 474

C 393 4.4 D32 475

C 400 4.5 D28 476

C 302 4.3 15 477

A 226 4.3 B120 478258 4.2388 4.4

C 256 4.1 B120 479395 4.4

231 ClOO 480251

system

C2-NiC-C! C-CiC-SN

N-NiC-CiC-CiC-C

N-NiC-CiC-CiC-C2

N-NiC-CiC-^iC-CC

N-NiC-Ci9-CiC-CC

N-NiC-CiC-CiO-C

N-NiC-CiC-CiC-C2C

N-N. C-C. C-C. C-CC

N-NiC-CiC-CiC-C2C

N-NiC-CiC-CiC-CC C

compound

3 , 3 f -diethylthiazolinocarboyanineiodide

2 ,4-hexadienal p-nitrophenylhydrazone

2 , 4~hexadienal N-methyl-2 , 4-dinitro-phenylhydrazone

9-methyl-2 , 4 , 8-decatrienal semicarbazone

5 , 9-dimethyl-2 , 4 , 8-decatrienal 2 , 4-di-nitropheny Ihydrazone ; 9-apolycopenal2 , 4-dinitropheny Ihydrazone

5 , 9-dimethyl-2 ,4 ,8-decatrienal semicarb-azone; 9-apolycopenal semicarbazone

4-methyl-2 , 4-hexadienal 2 , 4-dinitro-pheny Ihydrazone

4-methyl-6- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) -2 , 4-hexadienal phenylsemi-carbazone

3-methyl-5-(l-hydroxy-2,2,6-trimethyl-cyclohexy 1) -2 , 4-pentadienalsemicarbazone

2,6, 6-trimethyl-2-cyclohexenylidene-acetaldehyde phenylsemicarbazone

2-methyl-4-(2, 6 , 6-trimethylcyclohexyl-idene) -2-butenal phenylsemicarbazone

3,5-octadien-2-one semicarbazone

3 , 5-octadien-2-one phenylsemicarbazone

6 , 10-dimethyl-3 , 5 , 9-undecatr ien-2-one2 , 4-dinitropheny Ihydrazone ;^-ionone 2 , 4-dinitropheny Ihydrazone

6 , 10-dimethyl-3 , 5 , 9-undecatr ien-2-onesemicarbazone; ^-ionone semicarbazone

4- (3 , 3-dimethyl-l-cyclohexenyl) -3-buten-2-one 2, 4-dinitropheny Ihydrazone

solv. 'Vax. loge ref. no.

444 B137 481

M 235 4.3 B84 482291 4.2414 4.6

M 290 4.3 B84 483410 4.4

A 305 4.7 B155 484

C 265 4.7 K60 485308 4.6400 4.7

A 304.5 4.7 B156 486

C 242 4.4 H3 487260 4.4392 4.6

PE 234.5 4.2 112 488304-6 4.7

M 300 4.6 14 489

PE 236 4.2 112 490308.5 4.6

PE 245.5 4.2 112 491314 4.8

M 313 4.7 14 492

M 290 B87 493

M 300 B87 494

A 228 4.2 B120 495395 4.5

C 257 4.3 B120 496309 4.3407 4.5

A 299.5 4.7 B156 497

285 4.1 S36 498

system

N-N: c-c !9-0: c-cC C

N-N : cc : c-c : C-C2C C

O-N:C-C:C-C:C-C

N~N:6c-c.-c-c.-c*0*0 C2

M NT*-0'0-010-0N-N.C

system

N-N : c~c : C-CiC-C :c-c2

N-N: c-c: c-c: c-c: C-C2C

N-N : c-c . c-c : c-c : C-C2C

N-N: c-c: c-c: c-c: c-cC C

N-N: c-c: c-c: c-c: c-c

N-N: c-c: c-c: c-c: c-c

(N: c) (c :c)4-Nc4

(N:c)(c:c)4-Nc5(N:c)(c:c)5-NC5

(N:c)(c:c)6-oc4

(N: c)(c: C)7-Nc6

compound

7 , 11-dimethy 1-2 ,4,6, 10-dodecatetraenalsemicarbazone; 12-apolycopenal semi-carbazone

7 , ll-dimethyl-2 ,4,6, 10-dodecatetraenalphenylsemicarbazone ; 12-apolycopenalphenylsemicarbazone

4-methyl-6- (2,6, 6-trimethylcyclo-hexylidene) -2 , 4-hexadienal phenylsemi-carbazone

8-methoxy-2 , 7-dimethyl-2 , 4 , 6-octatrienal2 , 4-dinitrophenylhydrazone

8-methoxy-2 , 7-dimethyl-2 , 4 , 6-octatrienalsemicarbazone

2,6-dimethyl-8-(2,6,6-trimethyl-l-cyclo-hexenyl) -2,4, 6-octatrienal phenyl-semicarbazone

2-methyl-4- (2,6, 6-trimethyl-2-cyclo-hexenylidene) crotonaldehyde semi-carbazone

2-methy 1-4- (2,6, 6-trimethy 1-2-cyclo-hexenylidene) crotonaldehyde phenyl-semicarbazone

5 , 6-dihydro-6-hydroxy-13-apocarotenonesemicarbazone

2 , 6-dimethyl-8- (2 , 2 , 6-trimethylcyclo-hexy lidene) -2,4, 6-octatrienal phenyl-semicarbazone

4-methyl-6- (2 , 6 , 6-trimethy 1-2-cyclo-hexenylidene) -2 , 4-hexadienal phenyl-semicarbazone

13-apo- B-carotenone semicarbazone

retinal semicarbazone

2 , 6-dimethy 1-8- (2,6, 6-trimethy 1-2-cyclo-hexenylidene) -2,4, 6-octatrienalphenylsemicarbazone

5 , 6-dihydro-5 , 6-dihydroxy-10 T -apo-3-carotenal oxime; apo-1-azafrinaloxime

3-apo-4-carotenal semicarbazone

solv. max. loge ref. no.

A 325.5 4.4 B156 515

A 236.5 4.2 B156 516332 4.4

PE 236 4.3 112 517340 4.9

C 407 4.6 A12 518

A 328 4.7 A12 519

PE 234 4.2 112 520332 4.9

PE 335.5 4.7 112 521

PE 234 4.2 112 522340 4.8

A 235 3.7 A41 523325 4.8

PE 238 4.5 112 524369 5.0

PE 366 4.9 112 525

A 345 4.7 A41 526

375 4.9 07 527

PE 236.5 4.4 112 528393 5.0

A 423 KIl 529

CD 445 KIl 530

A 4^45 K18 531

system

(NiC)(CiC)7-OC6

(NiC)(CiC)8-OC5

(NiC)(CiC)9-OC7

(NiC)(CiCJn-OC90-NiC-CiC-CiN-O

C-CiC-CiN-NiC-CiC-C

N-NiC-CiC-CiC-CiN-N

(NiC)2(CiC)4-C2

(NiC)2(CiC)6-C2

(NiC)2(CiC)8-C2

(NiC)2(CiC)8-O2N4

(NiC)2(CiC)9-O2N4

compound

3-apo-4-carotenal oxime

a-apo-2-carotenal oxime

3-apo-2-carotenal oxime

$-caroten-4-one oxime

3-carene-2 , 5-dione dioxime

di- (2-butanylidene)hydrazine ;crotonaldehyde azine

3 , 5-octadiene-2 ,7-dione semicarbazone

3 , 5-octadiene-2 , 7-dione phenylsemi-carbazone

di-2 , 4-hexadienylidenehydrazine ;2 ,4-hexadienal azine

di-2 , 4 , 6-octatrienylidenehydrazine ;2 ,4,6-octatrienal azine

di-2 ,4,6, 8-decatetraeny lidenehydrazine ;2,4,6,8-decatetraenal azine

6,8?-diapolycopenedial oxime;apo-1-bixindialdehyde oxime

6,6 f-diapolycopenedial oxime;bixindialdehyde oxime

solv. max. loge ref. no.

CD 474 K18 532

A 409 K18 533

CD 456 K18 534

A 439 KIl 535

CD 469 KIl 536

A 445 K18 537

CD 473 K18 538

H 456 PlO 539

278 4.4 C97 540

A 275 4.6 B76 541

D 275 4.6 B76 542

M 330 B87 543345

M 343 B87 544355

A 338 4.9 B26 545

D 327 4.8 B76 546342 4.8

A 385 4.9 B26 547

D 245 4.1 B76 548304 4.1372 4.9

*1 343 3.6 B76 549410 4.2

A 449 KlO 550481

CD 480 KlO 551510

Py 452 K69 552482514

*1 tetrachloroethylene

system

N-N: c-c :.c-c

N-N .C-Ci C-Ci C-C

N-N: c-c :c-c;c-cC

S-N. c-c; c-c: c-c

N-N:c-c:c-c:9-c;cC CV-i V->

N-N: c-c :c-ci c-(p: c-c2C C

N-N:C-C:C-C:C-C;C-CC C

(N: c) (c; c) (C !O3-NC5

compound

2-butynal 2 , 4-dinitr opheny lhydr azone ;tetrolaldehyde 2 , 4-dinitrophenyl-hydrazone

4 , 4-dimethyl-2-pentynal semicarbazone

6 , 6-dimethyl-2 , 4-hep tadiynal 2 , 4-dinitr opheny Ihydrazone

6 , 6-dimethyl-2 , 4-heptadiynal semi-carbazone

5- (l-hydroxy-2 , 2 , 6-trimethylcyclohexyl) -3-methyl-2-penten-4-ynal semicarbazone

6 ,6-dimethyl-4-hepten-2-ynal semi-carbazone

6-methyl-3 , 5-octadien-7-yn-2-one semi-carbazone

3-methyl-5- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) -2-penten-4-ynal 2 , 4-dinitro-pheny lhydr azone

3-methyl-5- (2 , 6 , 6-trimethyl-l-cyclo-hexenyl) -2-penten-4-ynal semicarbazone

8- (l-hydroxy-2 , 2 , 6-trimethylcyclohexyl) -6-methyl-3 , 5-octadien-7-yn-2-one semi-carbazone

6-methyl-8- (2,6, 6-tr imethy 1-1-cyclo-hexenyl) -3 , 5-octadien-7-yn-2-onesemicarbazone

solv. max. loge ref. no.

C 363 4.4 L32 553

265 4.3 B89 554

M 365 4.5 B90 555

M 222 4.2 B90 556305 4.5

M 295 4.5 14 557

M 290 4.5 B90 558

A 313 4.7 A41 559

M 265 4.2 14 560395 4.5

M 240 4.2 14 561318 4.4

A 232 3.6 A41 562316 4.7

A 342 4.6 A41 563

PART 6. (NiC)-, (N:C:N)-, AND (N:N:C)-CHROMOPHORES

system

NiC-C

N-C-N

NiC-S

NiC-I

NiC-CiN

NiC-CiC

N;C-C:C-C

N i c-c : c-cC

N;C-C:C-C:C-C

Nic-c:c-c:c-c2Vj

N;C-C:C-C:C-C:CNic-c:c-c:c-c:c-c2

NiC-C'.C-CiN

Nic-c:c-c:9-c;NC C

C-N:C:N-C

N:N:C

N:N:C-C

compound

ethanonitrile; acetonitrile

trichloroethanonitrile; trichloroaceto-nitrile

N-cyanodiallylamine

butyl thiocyanate

iodine cyanide

ethanodinitrile; oxalonitrile; cyanogen

propenonitrile; acrylonitrile

2-butenonitrile; crotononitrile

22-cyano-33-hydroxy-5,20-bisnor-choladiene

33,21-diacetoxy-20-cyanopregna-5,17(20)-diene

3-methyl-5- (2,6, 6-trimethyl-2-cyclo-hexeny 1) -2 , 4-pentadienonitrile

3 B-acetoxy-17 3-cyano-5 3-andros ta-14 , 16-diene

2,4, 6-heptatrienonitrile

3-methyl-5- (2 , 6 , 6-tr imethyl-1-cyclo-hexenyl) -2 , 4-pentadienonitrile

1 , 2-dicyano-cis-ethylene ; maleonitrile

2 , 5-dicyano-2 , 4-hexadiene

diethylcarbondiimide

diazome thane

diazoethane

solv. max. log e ref. no.

V 160 H57 564

305 DlIg 565

iO no S2g 566

cH 242 S2g 567

A 224 2.3 HIS 568

PE 242 2.2 H18 569

V 220 0.3 H74 570

A 215.5 1.7 R27n 571

H 250 0.5 C18 572

A 226 4.1 H52u 573

A 224 4.0 H34 574

A 262.5 4.3 Y3 575

A 286 4.3 R48 576

261 Cl 577

A 256 4.2 Y3 578300 4.1

M 220 4.1 W6x 579

M 268 4.4 E16 580

H 230 2.3 L3 581270 1.4

A 347.5 0.7 H8 582

V 4^10 0.5 B128 583

V 4^5O 0.5 B128 584

Next Page

PART 7. (OrC)-CHROMOPHORES

system

o:c

o:c-c

o:c-c2

compound

formaldehyde

butyraldehyde

monoanhydrodihydrostrophanthidin

acetone

4-methyl-2-pentanone

2,2,4, 4-tetramethyl-3-pentanone ;tert-butyl ketone

bromoacetone

ace ty !cyclopropane

acetylcyclobutane

acetylcyclopentane

acetylcyclohexane

dicyclopropyl ketone

cyclobutanone

cyclopentanone

3$,203-diacetoxy-5a-pregnan-16-one

3a-hydroxy-5a-androstan-17-one ;androsterone

cyclohexanone

1 , 3-dioxane-2-spiro-2 ! -cyclohexanone

17 (3-hydroxyalloandrostan-3-one

solv. max. loge ref. no.

A 305 1.2 R14 585

A 282.5 1.1 L17 586

H 290 1.3 L18 587

A 303 1.4 E9 588

A 272 1.2 S17 589

C 277 1.2 S17 590

H 279 1.2 S17 591

M 270 1.2 S17 592

W 264.5 1.2 S17 593

A 279 1.4 M12 594

A 295 1.3 R13 595

H 215 2.6 M47 596299 1.9

A 271 1.4 M12 597

A 281 1.5 M12 598

A 279 1.4 M12 599

A 281 1.4 M12 600

system

o.c-c.o

O.CHSiOC

-n

compound

3-acetoxy-5a-cholestan-6-one

5a-cholestan-7-one

24-methyl-3 3-acetoxy-5a-cholestan-ll-one ;3$-acetoxyergostan-ll-one

33-acetoxy-12ot523-dibromo-5a-spirostan-11-one

1,3, 3-tr imethyl-2-norbornane ; f enchone

cycloheptanone

2,2,7 , 7-tetramethylcyclooctanone

2,4-pentanedione; acetylacetone

2,2,5, 5-tetramethyl-l , 3-cyclohexanedione

ethyl 2,2-dimethylacetoacetate

ethanedial; glyoxal

pyruvaldehyde

3a-acetoxy-12a-bromo-ll,20-dioxo-5B-pregnan-21-al

2,3-butanedione; diacetyl

2 , 5-dimethy 1-3 , 4-hexanedione

2,3-bornanedione; camphorquinone

3- [ 3- (methoxycarbonyl) propionyloxy ] -ll,12-dioxo-5B-cholanoic acid

ll,12-dioxo-53-cholanoic acid

3,3,6, 6-tetramethyl-l , 2-cyclohexanedione

solv. max. loge ref. no.

280 1.6 B35 609

A 292 1.6 W41 610

A 290 1.7 H58 611

D 316 2.2 D23 612

H 293 1.3 D18 613

H 281 1.3 C17 614

A 293 1.5 L12 615

CCl4 274 2.0 VIl 616

A 207 3.0 M28 617274 2.4

H 285 1.5 B113 618

W 267.5 0.8 M6 619

W 282.5 1.4 M6 620

A 282 F36 621

A 284 1.1 C73 622418 0.0

A 285 1.7 L12 623365 1.3

A 466 1.5 L12 624

cH 259.5 1.3 A15n 625270 1.3280 1.3477 1.6484 1.6

A 284 2.1 D27 626

H 2^22 2^.1 B33 627279 1.9347 1.7

A 297.5 1.5 L12 628380 1.0

system

o:c

system

o:c-c:c-oO

O:C-C:C-NO

O:C-C:C~No:c-:cC

o:c-c:c-cC

0Wo:c-c:c-c2

C

compound

3a,20-diacetoxy-ll-oxo-5$-pregn-17(20)-en-21-al

2 , 3-dibenzoyloxyacrylaldehyde

2-hydroxy-3- (N-methy lanilino) acryl-aldehyde

2-hydroxy-3- (p-chloroanilino) acryl-aldehyde

2-hydroxy-3- (p-ethoxycarbony lanilino) -acrylaldehyde

2-benzoyloxy-3- (N-methy lanilino) acryl-aldehyde

3-anilino-2-bromoacry !aldehyde

3-buten-2-one; methyl vinyl ketone

3-hepten-2-one

2-cyclohexen-l-one

53-cholest-l-en-3-one; coprost-1-en-3-one

2-methyl-l-penten-3-one

l-cyclopropyl-2-methyl-2-propen-l-one

4-methyl-3-penten-2-one; mesityl oxide

solv. max. loge ref. no.

E 246 4.2 F36 649

A 254 4.5 C69 650

A 236 3.7 C69 651342 4.6

C 342 4.6 C69 652

C 346 4.7 C69 653

A 276 3.7 C69 654358 4.7

C 357 4.8 C69 655

A 231 4.3 C69 656305 4.5

C 323 4.6 C69 657

A 219 3.6 E21 658324 1.4

A 228 4.0 E21 659310 1.6

A 225 4.2 B96 660

A 230 4.0 15 661

A 220 3.9 E21 662319.5 1.4

215 4.0 H9 663. 305 1.6

A 235 4.1 E21 664313.5 1.8

E 230 4.1 S17 665326 1.6

H 229.5 4.1 S17 666327 1.6

M 238 4.0 W49 667315 1.7

W 244.5 4.0 S17 668305 2.0

system

o:^ :c-c

compound

3 |3-acetoxy-17-acetonylideneandrost-5-enecyclohexylideneacetone

3-methyl-2-cyclopenten-l-one

3-methyl-2-cyclohexen-l-one

4a-methyl-2 ,3,4,4a,5,6,7, 8-octahydro-2 , 5-naphthalenedione

cholest-4-en-3-one

6-bromopregn-4-ene-3 , 20-dione ;6-bromoprogesterone

3 $-acetoxycholest-5-en-7-one

1, 4-epidioxidocholesta-2 ,5-dien-7-one

5-hydroxy-5a-cholest-7-ene-3,6-dione

methyl 3a-(ethoxycarbonyloxy)-12-oxo-5 3-chol-9 (11) -enoate

3-thujen-2-one; umbellulone

2-pinen-4-one; cedrone

3-methyl-3-penten-2-one

3a-acetoxy-5$-pregn-16-ene-ll, 20-dione

1-acetylcyclopentene

1-acetylcyclohexene

l-acetyl~l , 4-cyclohexadiene

1-acetylcycloheptene

l(6)-p-menthen-2~one; carvone

2,6, 6-trimethyl-2-cyclohepten-l-one ;y, 6-dihydroeucarvone

cholest-5-en-4-one

cholest-4-en-6-one

solv. VaX. log e ref. no.

A 242 4.3 P32 669

A 242 4.0 D18 670

M 225 4.3 A4 671

A 235 4.1 E21 672310 1.7

A 243 4.1 WlO 673

A 241 4.2 F18 674

A 248 4.2 S51 675

A 234 4.2 E3 676

A 232 4.1 H46 677

A 249 4.2 F18 678

239 4.0 F31 679

220 3.7 G14 680265 3.5

A 240 4.0 E21 681326 1.4

A 229.5 4.0 E21 682310 1.6

A 238 4.1 R34 683312 1.8

239 4.1 S30n 684

233 4.1 S30n 685

A 245 3.6 E17 686

236 4.0 S30n 687

A 235 4.3 C85 688318 1.6

239.5 3.9 C98 689

241 3.9 B164 690

A 243 3.8 RlO 691

system

0:^ :0-0,

o : C-C:C-NC

o : c-c : C-NCC

compound

3 , 4-dimethyl-3-penten-2-one

2-isopropylidene-4-methylcyclopentanone

2-isopropylidene-5-methylcyclohexanone

2-cyclopentylidenecyclopentanone

2-cyclohexylidenecyclohexanone

4(8)-p-menthen-3-one; pulegone

bicyclohexyliden-2-one

l-acetyl-2-methylcyclopentene

l-acetyl-2-methylcyclohexene

2-methyl-3-pentyl-2-cyclopenten-l-one;dihydro j asmone

one

2- (1 , 4a-dime thy l-2-oxo-2 , 3 , 4 , 4a , 5 , 6 , 7 , 8-octahydro-7-naphthyl) propionic acid

12(23)-dehydronor-5B-cholen-22-one

33-acetoxy-5a-cholest-8-en-7-one

methyl 3a-acetoxy-ll-oxo-5 3~chol-8-enoate

33-acetoxy-5a-cholest-8(14)en-15-one

33-hydroxy-5a-cholest-8(14)-en-7-one

l-(diethylamino)-l-hexen-3-one

l-anilino-l-hexen-3-one

4-amino-3-penten-2-one

2 , 5-dimethyl-4-oxo-l-phenyl-2-pyrroline

solv, max. loge ref. no.

A 247 3.9 M27 692

A 254 4.0 F48 693

H 247 4.0 F48 694

A 252 3.8 F48 695

H 242 4.0 F48 696

A 259 4,0 F48 697

A 255 3.8 F48 698

A 245 3.7 C85 699324 1.6

A 255 3.8 F48 700

253 4.0 S30n 701

249 3.8 S30n 702

A 237 4.1 G13 703304 1.7

10 237 3.9 BlOl 704

A 250 4.5 Al 705

E 234 4.2 B161 706

A 253 4.2 F20 707

A 254 3.9 H61 708

A 259 4.1 W40 709

A 261 3.9 F29 710

A 215 3.1 B99 711307 4.4

A 227 4.0 B99 712340 4.4

Hp 285 3.8 CIlO 713

A 246.5 3.4 D12 714324.5 4.2

system

o : c-c '.c-ocC

o:n:c-o:^ :c-oc

compound

4-hydroxy-3-penten-2-one[enol form of acetylacetone]

3-hydroxy-4 , 4 (or 5 , 5) -dimethyl-2-cyclo-penten-1-one [enol form of4,4-dimethyl-l,3-cyclopentanedione]

3-hydroxy-5 , 5-dimethyl-2-cyclohexen-1-one [enol form of 5, 5 -dime thy 1-1,3-cyclohexanedione] ; dimedone

4-methoxy-3-penten-2-one [enol methylether of acetylacetone]

3-methoxy-5 , 5-dimethyl-2-cyclohexen-1-one [enol methyl ether of5 , 5-dimethyl-l , 3-cyclohexanedione ]

3-hydroxymethylene-2-bornanone ;hydroxymethylenecamphor

2-acetyl-l-cyclohexen-l-ol[enol form of 2-acetylcyclohexanone]

3-hydroxy-2 , 4-dimethyl-2-cyclobuten-1-one [enol form of 2,4-dimethyl-l,3-cyclobutanedione]

2-ethyl-3-hydroxy-4 (or 5) -propyl-2-cyclo-penten-l~one [enol form of 2-ethyl-4~propyl-l,3-cyclopentanedione]

solv. max. log e ref. no.

*1 338 4.0 D12 715

A 273 3.9 M29 716

C 280 4.0 B48 717

*3 275 3.3 E8 718

*4 287 4.3 E8 719

*5 293 4.3 E8 720

*3 244 4.3 E8 721

*4 254 4.3 E8 722

*5 259 4.4 E8 723

A 255 4.3 M28 724

*3 259 4.2 E8 725

*4 277 4.3 E8 726

*5 282 4.4 E8 727

CCl4 250 VIl 728

A 250 4.3 M28 729

A 264.5 4.1 GlO 730

*3 295 3.5 E8 731

*4 308 4.1 E8 732

*5 310 4.2 E8 753

*3 245 4.1 E8 734

*4 261 4.1 E8 735

*5 256 4.2 E8 736

- A 252 4.2 G3 737

*1 0.01N NaOH/W *2 0.002M NaOH/M *3 cone. H2SO4 *4 dil. H2SO4 *5 5N NaOH

system

0:^ :0-0

o:n:c-c2

compound

3-hydroxy-2- ( 1-methoxycarbony 1-1-methy 1-ethyl) -4 , 4 (or 5 , 5) -dimethyl-2-cyclo-penten-1-one [enol form of 2-(l-methoxycarbonyl-1-methylethyl) -4 , 4-dimethyl-1 , 3-cyclopentadiene]

3-hydroxy-2 , 5 , 5-trimethyl-2-cyclohexen-1-one [enol form of 2 ,5 , S-trimethyl-l^-cyclohexanedione]

3-ethoxy-2 , 5 , 5-tr imethy 1-2-cyclohexen-1-one [enol ethyl ether of 2,5,5-trimethyl-l,3-cyclohexenedione]

5-hydroxy~2 , 2-diphenyl-4-cyclopenten-1-one

3-hydroxy-5a-cholest~3-en~2-one

2-hydroxy-5a-cholest-l-en-3-one

3-acetoxy-5a-cholest-3-en~2-one

2-acetoxy-5a-cholest-l-en-3-one

2-hydroxy-3-methyl-2~cyclohexen-l-one[enol form of 3-methyl-l,2-cyclo-hexanedione]

2-hydroxy-l-p-menthen-3-one ; diosphenol

4-hydroxycholest-4-en-3-one [enol formof 3,4-cholestanedione]

33,ll-dihydroxy-22-isoallospirost-9(ll)-en-12-one [enol form of 3{3-hydroxy-22-isospirostane-ll, 12-dione]

4-methoxycholest-4-en-3-one [enol methylether of 5ot-cholestane-3,4-dione]

2-acetoxy-l-p-menthen~3-one ; diosphenolacetate

4-acetoxycholest-4-en-3-one [enolacetate of 5a-cholestane-3,4-dione]

solv. max. loge ref. no.

*1 250 4.2 E8 738

*2 265 4.3 E8 739

*3 268 4.4 E8 740

A 264 4.1 M28 741

*1 268 4.1 E8 742

*2 291 4.2 E8 743

*3 295 4.3 E8 744

A 268 4.3 M28 745

*4 305 G3 746

E 272 3.9 S73 747

E 270 3.9 S73 748

E 248 3.9 S73 749

E 237 3.9 S73 750

A 268.5 3.9 F45 751

W 269 3.9 F45 752

*5 312 3.9 F45 753

A 274 4.0 GlO 754

A 278 4.1 S71 755

C 280 4.0 B162 756

A 282 3.3 D27 757

A 263 3.7 S71 758

A 240 GlO 759

C 247 4.2 F33n 760

*1 cone. H2SO4 *2 dil. H2SO4 *3 5N NaOH *4 KOH/W *5 O. IN NaOH/W

system

o :c-c c-sC

o : c-c : c-ciC

o:?1.c-d

o:c-c:c-BrC

0:^ .0-0

o:n:c-c2

o:n.c-Br

o : c-c:c-oc

*2H

^ ;^ z

o^ ;^.-%2&cZcl

o:ccc:

compound

33,ll-diacetoxy-22-isoallospirost-9(ll)-en-12-one [enol acetate of 33-acetoxy-22-isospirostane-ll,12-dione]

l-ethylthio-l-penten-3-one

l-chloro-l~-buten-3-one

1 , 2-dichloro-l-penten-3-one

l-bromo-l-penten-3-one

2-bromo-5(3-cholest-l-en-3-one

4-bromocholest-4-en-3-one

1 , 2-dibromo-l-penten-3-one

2-bromo-3-hydroxy-5 ,5-dimethyl-2-cyclo-hexen-1-one [enol form of 2-bromo5,5-dimethyl-l,3-cyclohexanedione]

33-acetoxy-5a-cholesta-8 , 14-dien-7-one

17a-hydroxyandrosta-l , 4-dien-3-one

2 , 6 -dime thy 1-2 , 5-heptadien-4-one ;phorone

dl-a-santonin

33-acetoxylanosta-5 , 8-dien-7-one

1- (diethylamino) -1 , 4-hexadien-3-one

1-anilino-l , 4-hexadien-3-one

solv. max. loge ref. no.

A 244 4.0 D27 761

H 292 4.2 B98 762

A 228 4.0 B98 763

M 248 3.8 B98 764

H 237 3.7 B98 765

M 256 3.9 D26 766

E 250 4.2 D7 767

H 259 3.8 B98 768

*1 276 4.1 E8 769

*2 306 4.2 E8 770

*3 293 4.3 E8 771

A 224 4.2 F29 772298 3.7

A 244 4.2 W26 773

E 236 4.2 18 774

H 259 4.4 S17 775375 1.9

A 242 4.0 A2 776

A 249 4.1 B39 777

A 242.5 4.0 B99 778339 4.4

A 240 4.2 B99 779377 4.5

*1 cone. H2SO4 *2 dil. H2SO4 *3 5N NaOH

system

Q-C?:C-'

c

system

o:c-c:c-c:c-c2Li

o:c-c:c-c:c-cC C

o:c-c:c-c:c-cC C

o:c-c:c-c:c-c

o:c-c: c-c :c-c2

TT?"o:n:c"

system

o:nr:c-c

0:9-9 : c-c:c-cC Br C

'nn?-c

;Ht:rrBrc

:cb-c:%br?%b:-cBr-0'0 Co-t%~o:c-c:c-c:c-c:c-c

o:c-c:c-c:c-c:c-c2

o:c-c:c-c:c-c:c-c2C

o.G-c:c-c:c-c:c-c2

o:c-c:c-c:c-9:c-cC C

compound

3-methoxycholesta-3 , 5-dien-7-one

3-acetoxycholesta-3 , 5-dien-7-one

4-hydroxycholesta-4 , 6-dien-3-one ;diosterol I

4-benzoyloxycholesta-4,6-dien-3-one;diosterol I benzoate

6-bromocholesta-3 , 5-dien-7-one

4 , 6-dibromocholesta-4 , 6~dien-3~one

4,6-dibromocholesta-3,5-dien-6-one

4,6, 7-tribromocholes ta-4 , 6-dien-3-one

22-spirosta-l,4,6-trien-3-one

3-acetoxy-4,4~dimethylcholesta-5 ,8,11-trien-7-one ; 3-acetoxylanosta-5 , 8 , 11-trien-7-one

2 , 4-dibromocholesta-l , 4 , 6-tr ien-3-one

3-acetoxy-24-methyl-5 -cholesta-6 ,8,14-trien-11-one; 3-acetoxyergosta-6,8, 14-tr ien-11-one

2,4, 6-octatrienal

7 , ll-dimethyl-2 ,4,6, 10-dodecatetraenal

4-methyl-6- (2,6, 6-trimethylcyclo-hexylidene) -2 , 4-hexadienal

8-methoxy-2 , 7-dimethyl-2 , 4 , 6-octatrienal

2 , 6-dimethyl-8- (2,6, 6-trimethyl-l-cyclo-hexenyl) -2,4, 6-octatrienal

solv. max. loge ref. no.

393 4.8 B34 823

A 308 4.4 B34 824

A 283 4.4 B34 825

A 313.5 3.7 F23 826

A 232 4.2 F23 827287 4.4

A 280 4.3 J2 828

C 296 4.3 J2 829

A 303 4.0 J2 830

C 313 4.2 J2 831

A 222 4.1 Y2 832296 4.2

A 258 3.9 B39 833326 3.9

A 326 4.1 13 834

A 233 4.2 F29 835326 3.9

A 315 4.6 B76 836

D 312 4.6 B76 837

M 306 4.6 B76 838

A 314 4.1 B156 839

H 307 4.1 B156 840

PE 323 4.7 112 841

A 323 4.5 A12 842

PE 313 4.8 110 843

system

0.C-CiC-CiC-CiC-C2C C

OiC-Cic-CiC-CiC-cC C C

OiC-Cic-c.c-c.cC C

OiC-CiC-CiC-^.c-c

OiC-ciC-CiC-CiC-cC C

OiC-CiC-CiC-CiC-C2C C C

O-CX^ 0"0^0-J*c.'c-c:c-c^

(0:0 (CiO4-C

(o:c) (c:c)4-c4

(OiC) (c:c)4-c

(OiC)(CiO5-C

compound

3-methyl-5- (2,6, 6-trimethyl-l-cyclo-hexenyl) -2 , 4-pentadienal

2-methyl-4-(2,6 , 6-trimethyl-2-cyclo-hexenylidene) -2-butenal

6-methyl-3,5 ,7-octatrien-2-one

6-methyl-8- (2 , 6 , 6-trimethyl-2-cyclo-hexenyl)-3,5 , 7-octatrien~2-one

cholesta-1 , 3 , 5-trien-7-one

4-methyl-6- (2,6, 6-tr imethy 1-1-cyclo-hexenyl) -3 , 5-hexadien-2-one

spirosta-22-4 , 6 ,8-trien-3-one

24-methylcholesta-4 , 6 , 8 (14) -trien-3-one ;ergosta-4 ,6,8 (14) -trien-3-one

2 ,6-bis (perhydro-1-naphthylidene-ethylidene) -1-cyclohexanone

2,4,6, 8-decatetraenal

2 , 6-dimethyl-8- (2,2, 6-trimethylcyclo-hexylidene) -2 , 4 , 6-octatrienal

4-methyl-6- (2,6, 6-trimethyl-2-cyclo-hexylidene) -2 , 4-hexadienal

13-apo- 3-carotenone

2,4,6,8, 10-dodecapentaenal

solv. max. loge: ref. no.

10 265 4.1 WlOg 844315 4.2

PE 318 4.5 112 845

A 311 4.5 A41 846

H 303 4.5 A4 847

A 329 4.5 K15 848

A 230 4.2 H46 849350 3.9

A 285 4.1 Y4 850

A 244 4.2 Y2 851388 4.1

A 348 4.4 B37 852

E 342 5.0 F48 853

A 240 3.5 B76 854353 4.3

D 343 4.6 B76 855

PE 356 112 856

PE 353 4.7 112 857

A 345 4.4 A41 858

H 331 4.5 A41 859

A 263 4.0 B76 860377 4.7

An 380 4.8 B76 861

C 268 3.9 B76 862380 4.9

D 264 3.8 B76 863370 4.8

system

(o:c) (CiO5-C5

(o : c) (c :c)6-c

(0:0 (c:c)6-c4

(o : c) (c :c)6-c5

(o:c)(c:c)7-c

(o:c) (CiC)7-C6

(o:c)(c:c)8-c5

(OiC)(CiC)8-C5

(OiC)(CiC)0-C,7 D

(o:c) (CiC)9-C7

compound

retinal

2 , 6-dimethyl-8- (2,6, 6-tr imethyl-2-cyclo-hexenylidene) -2 , 4 , 6-octatr ienal

2 , 4 , 6 , 8 , 10 , 12- tetr adecahexaenal

5 , 6-dihydro-5 , 6-dihydroxy-12 f -apo-|3-carotenal; apo-1-azaf rinal

6 , 10-dimethyl-12- (2 , 6 , 6-trimethyl-l-cyclohexenyl) -3,5,7,9, 11-dodeca-pentaen-2-one

2 , 4 , 6 , 8 , 10 , 12 , 14-hexadecaheptaenal

12!-apo-3-carotenal; $-apo-4-carotenal

2,6,ll,15-tetramethyl-17-(2,6,6-tr imethyl-2-cyclohexeny 1) -2,4,6,-8 , 10 , 12 , 14 , 16-heptadecaoctaenal ;ot-apo-2-carotenal

capsochrome

8 T-apolycopenal; apo-3-lycopenal

8 * -apo-3-carotenal; 3-apo-2-carotenal

solv. max. loge ref. no.

A 250 3.9 B24n 864380.5 4.6

C 255 3.6 B24n 865389 4.6

PE 245 3.6 B24n 866369.5 4.7

PE 383 112 867

An 399 4.7 B76 868

D 285 4.1 B76 869393 4.8

CD 461 KIl 870

PE 431 KIl 871

A 401 4.7 K7 872

cH 395 4.8 K7 873

An 310 4.0 B76 874424 4.9

D 305 3.9 B76 875415 4.8

CD 4^6O K18 876

PE 4^42 K18 877

CH 484 KIl 878

PE 450 KIl 879

C 462 KIl 880

CD 482 KIl 881

B 488 KIl 882

CD 508 KIl 883

PE 473 KIl 884

A 4^98 K18 885

CD 525 K18 886

PE 484 K18 887

system

(o:c)(c:c)9-c5

(o:c)(c:c)10-c6

(OiC)(CiC)10-C7

(OiC)(CiC)11-C9

(OiC)(CiC)12-C9

OiC-CiC-CiO

OiC-CiC-CiOC C

o;rrto:mt

compound

25-(l,2-dihydroxy-2 ,6 , 6-trimethylcyclo-hexyl) -6 , 6 , 10 , 14 , 19 , 23-hexamethy 1-8 , 10 , 12 , 14 , 16 , 18 , 20 , 22 , 24-pentacosa-nonaene-2 ,7-dione; dihydroxysemi-3-carotenone

6 ! -apolycopenal; apo-2-lycopenal

6 , 10 , 14 , 19 , 23-pentamethyl-25- (2,6, 6-tr i-methy 1-1-cyclohexeny 1) -8 , 10 , 12 , 14 , 16 , -18 , 20 , 22 , 24-pentacosanonaene-2 , 7-dione ;semi- 3-carotenone

1- (2-acetyl-5 , 5-dimethyl-l-cyclopenten-yl)-3,7,12,16-tetramethyl-18-(2,6,6-tr imethyl-1-cyclohexenyl) -1,3,5,7,9,-11 , 13 , 15 , 17-octadecanonaene ;anhydrosemi-3-carotenone

3-caroten-4-one

3 , 4-dehydro-3-caroten-4 f -one

fumar aldehyde

3-hexene-2 ,5-dione

1 , 4 , 4a , 5 , 8 , 8a-hexahydro-5 , 8-methano-1 , 4-naphthalenedione

3-caren-2 ,5-dione

1 , 4 , 4a , 5 , 8 , 8a-hexahydro-2-methy 1-5 , 8-methano-1 , 4-naphthalenedione

cholest-4-ene-3 , 6-dione

33 5 26-diacetoxycholesta-5 , 17 (20) -diene-16,22-dione

4-methylcholest-4-ene-3 , 6-dione

3(3-acetoxy-5a-cholest-8-ene-7 9 11-dione

33-acetoxy-24-methyl-5a-cholest-8(14)-ene-7 , 15-dione ; 33-acetoxyergost-8 (14) -ene-7 , 15-dione

solv. max. loge ref. no.

A 4^71 K62 888

C 479 K62 889

CD 495 K62 890

PE 468 K62 891

CD 528.5 KIl 892

PE 490.5 KIl 893

C 4^87 K66 894

CD 499 K66 895

PE 470 K66 896

C 489 K63 897

CD 509 K63 898

PE 480 K63 899

H 458 PlO 900

H 470 5.1 PlO 901

iO 226 4.3 H83n 902332 1.6

H 226 4.2 BlOO 903338 1.8

A 222 4.1 W6 904

240 3.9 C97 905

A 237 4.1 C31 906354 1.8

A 252 4.0 F19 907

A 246 4.1 S5 908

A 258.5 4.0 F19 909

A 269 3.9 F28 910

A 255 3.7 S62 911

system

o:raf

"rawra n:o

:%ft

o:c-c:c-c:c-c:o

o:c-c:c-c:c-c:o

(o:c)2(c:c)3-c2

(O : c)(o: c) (c :c)7-c3

(o:c)2(c:c)8-c4

(o. -c)(o: c) (c .'C)8-C4

(o : c) 2 (c : O9-C4

(o:j)2(c:c)9-c4

compound

4 , 5-dichloro-4-cyclopentene-l , 3-dione

2,2,4, 5-tetrachloro-4-cyclopentene-l , 3-dione

4-bromp-5-chloro-4-cy clopentene-1 , 3--dione

2,2,4 , 5-tetrabr omo-4-cy clopentene-1 , 3--dione

3 $-acetoxy-4 , 4-dimethylcholes ta-5 , 8-diene-7 , 11-dione; 33-acetoxylanosta-5 , 8-diene-7 , 11-dione

2,4-hexadienedial; mucoaldehyde

3 , 5-octadiene-2 , 7-dione

2 , 7 -dimethyl-2 , 4 , 6-oc tatr ienedial

4 , 9 , 13 , 17 , 17-pentamethyl-16 , 21-dioxo-2 , 4 , 6 , 8 , 10 , 12 , 14-docosaheptaenal ;3-carotenone aldehyde

2,6,ll,15-tetramethyl-2,4,6,8,10,12,14,-16-octadecaoctaenedial ; apo-3 , 12-lycopenedial , apo-1-bixindialdehyde

21-hydroxy-2 , 6 , 11 , 15 , 19 , 19-hexamethyl-18-oxo-2 , 4 , 6 , 8 , 10 , 12 , 1