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SUPPLEMENTARY INFORMATION
New approach to synthesis of functional derivatives of nido-carborane:
Alkylation of [9-MeS-nido-7,8-C2B9H11]-
Maria V. Zakharovaa,b, Igor B. Sivaeva, Sergey A. Anufrieva, Sergey V. Timofeeva,
Kyrill Yu. Suponitskya, Ivan A. Godovikova, Vladimir I. Bregadzea *
a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991, Moscow, Russia b Present address: Department of Chemistry, Universite Laval, 1045 Avenie de la Medecine, G1V 0A6, Quebec City, Canada
Figure S1. 11B{1H} NMR spectrum of [9-Et(Me)S-nido-7,8-C2B9H11] (2) in CDCl3.
Figure S2. 11B NMR spectrum of [9-Et(Me)S-nido-7,8-C2B9H11] (2) in CDCl3.
Figure S3. 1H NMR spectrum of [9-Pr(Me)S-nido-7,8-C2B9H11] (3) in CDCl3.
Figure S4. 11B{1H} NMR spectrum of [9-Pr(Me)S-nido-7,8-C2B9H11] (3) in CDCl3.
Figure S5. 11B NMR spectrum of [9-Pr(Me)S-nido-7,8-C2B9H11] (3) in CDCl3.
Figure S6. 1H NMR spectrum of [9-Bu(Me)S-nido-7,8-C2B9H11] (4) in CDCl3.
Figure S7. 11B{1H} NMR spectrum of [9-Bu(Me)S-nido-7,8-C2B9H11] (4) in CDCl3.
Figure S8. 11B NMR spectrum of [9-Bu(Me)S-nido-7,8-C2B9H11] (4) in CDCl3.
Figure S9. 1H NMR spectrum of [9-Bn(Me)S-nido-7,8-C2B9H11] (5) in CDCl3.
Figure S10. 13C NMR spectrum of [9-Bn(Me)S-nido-7,8-C2B9H11] (5) in CDCl3.
Figure S11. 11B{1H} NMR spectrum of [9-Bn(Me)S-nido-7,8-C2B9H11] (5) in CDCl3.
Figure S12. 11B NMR spectrum of [9-Bn(Me)S-nido-7,8-C2B9H11] (5) in CDCl3.
Figure S13. 1H NMR spectrum of [9-BrCH2CH2(Me)S-nido-7,8-C2B9H11] (6) in CDCl3.
Figure S14. 11B{1H} NMR spectrum of [9-BrCH2CH2(Me)S-nido-7,8-C2B9H11] (6) in CDCl3.
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Figure S15. 11B NMR spectrum of [9-BrCH2CH2(Me)S-nido-7,8-C2B9H11] (6) in CDCl3.
Figure S16. 1H NMR spectrum of [9-EtOCH2CH2(Me)S-nido-7,8-C2B9H11] (7) in CDCl3.
Figure S17. 11B{1H} NMR spectrum of [9-EtOrCH2CH2(Me)S-nido-7,8-C2B9H11] (7) in CDCl3.
Figure S18. 11B NMR spectrum of [9-EtOCH2CH2(Me)S-nido-7,8-C2B9H11] (7) in CDCl3.
Figure S19. 1H NMR spectrum of [9-H2C=CH(Me)S-nido-7,8-C2B9H11] (8) in CDCl3.
Figure S20. 13C NMR spectrum of [9-H2C=CH(Me)S-nido-7,8-C2B9H11] (8) in CDCl3.
Figure S21. 11B{1H} NMR spectrum of [9-H2C=CH(Me)S-nido-7,8-C2B9H11] (8) in CDCl3.
Figure S22. 11B NMR spectrum of [9-H2C=CH(Me)S-nido-7,8-C2B9H11] (8) in CDCl3.
Figure S23. 1H NMR spectrum of [9-H2C=CHCH2(Me)S-nido-7,8-C2B9H11] (9) in CDCl3.
Figure S24. 11B{1H} NMR spectrum of [9-H2C=CHCH2(Me)S-nido-7,8-C2B9H11] (9) in CDCl3.
Figure S25. 11B NMR spectrum of [9-H2C=CHCH2(Me)S-nido-7,8-C2B9H11] (9) in CDCl3.
Figure S26. 1H NMR spectrum of [9-HC≡C(Me)S-nido-7,8-C2B9H11] (10) in CDCl3.
Figure S27. 13C NMR spectrum of [9-HC≡C(Me)S-nido-7,8-C2B9H11] (10) in CDCl3.
Figure S28. 11B{1H} NMR spectrum of [9-HC≡C(Me)S-nido-7,8-C2B9H11] (10) in CDCl3.
Figure S29. 11B NMR spectrum of [9-HC≡C(Me)S-nido-7,8-C2B9H11] (10) in CDCl3.
Figure S30. 1H NMR spectrum of [9-H2C=C=CH(Me)S-nido-7,8-C2B9H11] (11) in CDCl3.
Figure S31. 13C NMR spectrum of [9-H2C=C=CH(Me)S-nido-7,8-C2B9H11] (11) in CDCl3.
Figure S32. 11B{1H} NMR spectrum of [9-H2C=C=CH(Me)S-nido-7,8-C2B9H11] (11) in CDCl3.
Figure S33. 11B NMR spectrum of [9-H2C=C=CH(Me)S-nido-7,8-C2B9H11] (11) in CDCl3.
Table S1. Bond lengths distribution in [9-RMeS-nido-7,8-C2B9H11] derivatives in comparison
with [nido-7,8-C2B9H12]- anion.
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siv11172.11F19CPD
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-16.
60
-11.
49
-7.0
9
-3.9
0
Fig. S32
Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2013
Page 35
-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-8-7-6-5-4-3-2-10f1 (мд)
siv10133.11F19CPD
-37.
05
-35.
92
-29.
64
-28.
63
-26.
80
-25.
68
-23.
65
-22.
46
-18.
89
-17.
50
-16.
06
-12.
09
-10.
90
-7.1
0
-4.4
4
-3.3
4
Fig. S33
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Page 36
Table S1. Bond lengths distribution in [9-RMeS-nido-7,8-C2B9H11] derivatives in comparison with
[nido-7,8-C2B9H12]- anion
Bond aniona anionb SMe2-derivativec
first molecule SMe2-derivativec
second molecule Compound 7 Compound 5
B1-B2 B1-B3 B1-B4 B1-B5 B1-B6 B2-B3 B3-B4 B4-B5 B5-B6 B6-B2 B2-C7 B3-C7 B3-C8 B4-C8 B4-B9 B5-B9 B5-B10 B6-B10 B6-B11 B2-B11 C7-C8 C8-B9 B9-B10 B10-B11 B11-C7
1.761 1.773 1.767 1.793 1.799 1.755 1.762 1.756 1.823 1.758 1.716 1.712 1.718 1.719 1.795 1.764 1.782 1.779 1.779 1.803 1.555 1.607 1.831 1.853 1.614
1.757 1.777 1.775 1.795 1.798 1.758 1.770 1.747 1.820 1.763 1.715 1.715 1.731 1.738 1.796 1.764 1.781 1.782 1.768 1.804 1.564 1.622 1.813 1.841 1.621
1.740(5) 1.778(5) 1.774(4) 1.777(4) 1.795(4) 1.740(5) 1.769(5) 1.767(4) 1.797(4) 1.762(5) 1.690(5) 1.712(5) 1.740(5) 1.752(4) 1.749(4) 1.736(4) 1.779(4) 1.785(4) 1.775(5) 1.800(5) 1.525(4) 1.571(4) 1.775(4) 1.843(5) 1.623(5)
1.724(5) 1.769(5) 1.777(5) 1.768(5) 1.793(5) 1.728(6) 1.768(5) 1.771(5) 1.790(5) 1.757(5) 1.679(5) 1.704(5) 1.738(5) 1.744(5) 1.757(4) 1.736(4) 1.776(4) 1.788(5) 1.777(5) 1.796(5) 1.531(4) 1.582(4) 1.773(4) 1.851(5) 1.613(5)
1.755(3) 1.774(3) 1.774(3) 1.787(3) 1.811(3) 1.756(3) 1.778(3) 1.763(2) 1.811(3) 1.775(3) 1.698(2) 1.704(2) 1.725(2) 1.735(2) 1.759(3) 1.748(3) 1.796(3) 1.791(3) 1.800(3) 1.808(3) 1.550(2) 1.594(2) 1.780(3) 1.861(3) 1.637(2)
1.759(2) 1.782(2) 1.769(2) 1.782(2) 1.809(2) 1.757(2) 1.775(2) 1.771(2) 1.811(2) 1.773(2) 1.699(2) 1.707(2) 1.737(2) 1.736(2) 1.769(2) 1.741(2) 1.801(2) 1.795(2) 1.795(2) 1.812(2) 1.549(2) 1.591(2) 1.788(2) 1.863(2) 1.637(2)
a [nido-7,8-C2B9H12]- anion, refcode CENBUS1; b [nido-7,8-C2B9H12]- anion, refcode GUNHUS011; c [9-Me2S-nido-7,8-C2B9H11], refcode VYUHIG1, there are two independent molecules in the asymmetric unit cell References 1. F.H. Allen, Acta Crystallogr., 2002, B58, 380; (b) Cambridge Structural Database, 2012, Version 5.34
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