-
S1
SUPPORTINGINFORMATION
BMImHCO3:anIonicLiquidwithCarboxylatingProperties.SynthesisofCarbamateEstersfromAmines.
AntonellaDiNicola,AntonioArcadiandLeucioRossi*
DepartmentofPhysicalandChemicalSciences.UniversityofL’Aquila–ViaVetoiosnc.CoppitoI-67100L’Aquila–Italy.
[email protected].
TABLEOFCONTENTS
1Hand13CNMRspectraofcompounds3a-3l…………………………………………..S2–S23
Electronic Supplementary Material (ESI) for New Journal of
Chemistry.This journal is © The Royal Society of Chemistry and the
Centre National de la Recherche Scientifique 2016
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
9.12
3.42
2.33
0.96
2.14
1.00
3.45
4.05
4.07
4.08
4.10
4.64
0.51.01.52.0
0.90
1.09
1.10
1.12
1.13
1.14
1.15
1.15
1.16
1.19
1.20
1.21
1.23
1.30
1.31
1.34
1.65
1.66
1.67
1.69
1.70
1.89
1.89
1.92
1.92
NH O
O
CH3
3a
S2
-
0102030405060708090100110120130140150160
14.6
24.8
25.5
33.4
49.7
60.4
76.7
77.1
77.4
155.8
NH O
O
CH3
3a
S3
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.4
6
2.2
2
4.0
8
2.2
2
0.8
8
2.2
2
1.0
0
3.9
3
3.9
5
3.9
6
4.0
5
4.0
7
4.0
8
4.1
1
4.7
2
1.01.52.0f1 (ppm)
1.1
9
1.2
1
1.2
2
1.2
3
1.3
6
1.3
6
1.3
8
1.3
9
1.4
0
1.5
5
1.5
6
1.5
6
1.5
7
1.5
7
1.5
7
1.5
8
1.5
8
1.6
2
1.6
3
1.6
3
1.6
3
1.6
4
1.6
5
1.9
2
1.9
4
NH O
O
CH3
3b
S4
-
0102030405060708090100110120130140150160
14.62
23.47
33.20
52.60
60.42
76.74
77.06
77.38
156.13
NH O
O
CH3
3b
S5
-
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
4.2
2
12.1
6
3.0
1
1.0
9
2.6
7
1.0
0
3.6
1
4.0
0
4.0
1
4.0
3
4.0
4
4.0
5
4.0
6
4.0
8
4.8
10.81.01.21.41.61.82.0
f1 (ppm)
1.1
4
1.1
4
1.1
6
1.1
7
1.1
7
1.1
8
1.1
9
1.1
9
1.2
1
1.3
5
1.3
7
1.3
8
1.4
0
1.4
1
1.4
3
1.4
4
1.4
5
1.4
5
1.5
2
1.5
3
1.5
6
1.8
6
1.8
7
1.9
7
1.9
8
NH O
O
CH3
3c
S6
-
102030405060708090100110120130140150160
14.5
23.9
28.0
35.3
51.9
60.3
76.8
77.1
77.4
155.7
NH O
O
CH3
3c
S7
-
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.7
0
2.3
6
2.4
5
1.0
0
5.0
3
1.2
5
1.2
7
1.2
8
4.1
3
4.1
5
4.1
7
4.1
8
4.3
6
4.3
8
5.1
6
7.28
7.28
7.29
7.30
7.31
7.33
7.33
7.34
7.35
7.35
7.35
7.37
NH O
O
CH3
3d
S8
-
0102030405060708090100110120130140150160
14.6
45.0
60.9
76.8
77.1
77.4
127.4
127.5
128.6
138.7
156.7
NH O
O
CH3
3d
S9
-
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
15.0
1
5.8
5
1.1
2
2.2
7
1.0
0
3.5
1
3.5
3
3.5
5
3.5
7
3.6
6
4.0
4
4.0
6
4.0
8
4.1
0
4.5
9
CH3
NH O
O
CH3
0.81.01.21.41.61.8f1 (ppm)
0.8
9
0.9
1
0.9
4
0.9
7
1.0
0
1.0
3
1.0
5
1.0
7
1.1
1
1.1
4
1.1
7
1.1
8
1.1
9
1.2
1
1.2
3
1.2
4
1.2
7
1.3
2
1.6
1
1.6
2
1.6
4
1.6
6
1.7
1
1.7
1
1.7
4
1.7
5
3e
S10
-
102030405060708090100110120130140150160
14.6
18.1
26.2
26.2
26.4
28.8
29.0
43.3
51.2
60.4
76.7
77.1
77.4
156.2
NH
CH3
O
O
CH3
3e
S11
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1
(ppm)
3.5
7
3.7
5
2.1
9
1.0
2
1.0
3
5.2
0
1.2
2
1.2
4
1.2
6
1.4
9
1.5
0
4.0
6
4.0
8
4.0
9
4.1
0
4.1
1
4.1
2
4.1
2
4.1
3
4.1
4
4.1
5
4.1
6
4.1
8
4.8
2
4.8
6
4.8
7
4.9
3
5.1
1
7.25
7.26
7.27
7.27
7.28
7.29
7.30
7.32
7.34
7.36
7.36
7.36
7.38
7.38
7.39
NH
CH3
O
O
CH3
3f
S12
-
102030405060708090100110120130140150160
14.6
22.5
50.5
60.8
76.8
77.1
77.4
125.9
127.2
128.6
143.8
155.9
NH
CH3
O
O
CH3
3f
S13
-
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
3.0
7
1.9
5
1.9
2
1.9
2
9.1
3
1.3
3
1.3
5
1.3
7
4.2
9
4.3
0
4.3
2
4.3
4
4.4
4
4.5
1
7.20
7.24
7.26
7.28
7.31
7.33
7.34
7.34
7.37
7.37
7.38
7.39
7.40
7.40
7.41
7.42
N O
O
CH3
3g
S14
-
102030405060708090100110120130140150160
14.8
48.9
49.3
61.8
76.8
77.2
77.5
127.4
127.6
128.6
137.6
157.0
N O
O
CH3
3g
S15
-
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
109.77
68.84
36.69
1.00
25.94
1.25
1.27
1.29
1.30
1.33
1.36
1.38
1.41
1.44
1.45
1.60
1.63
1.67
1.69
1.73
1.78
1.81
1.84
2.77
3.46
3.48
3.50
3.51
4.11
4.13
4.15
4.16
7.28
N
CH3
O
O
CH3
3h
S16
-
102030405060708090100110120130140150160
14.8
25.6
25.7
28.1
30.2
54.6
61.0
77.3
156.4
N
CH3
O
O
CH3
3h
S17
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
3.97
2.18
1.00
0.98
4.21
1.32
1.34
1.35
4.22
4.24
4.26
4.28
6.65
7.06
7.08
7.10
7.28
7.31
7.33
7.33
7.35
7.38
7.40
7.42
NH O
O
CH3
3i
S18
-
102030405060708090100110120130140150
14.6
61.2
76.7
77.0
77.4
118.6
123.3
129.0
138.0
153.6
NH O
O
CH3
3i
S19
-
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
1.5 1.0 0.5 ppm
1.327
2.197
4.216
4.233
4.251
4.269
6.680
7.266
7.284
7.288
35.56
0.42
18.60
8.91
0.40
36.12
AD109 F3
HN O
OCl3j
S20
-
0102030405060708090100110120130140150160
14.5
61.4
76.7
77.0
77.4
119.8
128.3
129.0
136.6
153.5
Cl
NH O
O
CH3
3j
S21
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0
3.52
2.34
3.38
2.22
1.01
1.00
2.16
4.67
3.47
3.49
3.51
3.53
3.54
3.57
4.84
5.10
7.28
7.30
7.31
7.32
7.33
7.34
7.35
7.37
7.38
NH O
O
3k
1.01.52.0
1.11
1.12
1.13
1.16
1.16
1.18
1.19
1.19
1.22
1.32
1.35
1.38
1.60
1.61
1.62
1.63
1.64
1.69
1.70
1.71
1.73
1.74
1.74
1.94
1.97
S22
-
102030405060708090100110120130140150160
24.8
25.5
33.4
49.9
66.4
76.8
77.2
77.5
128.0
128.1
128.3
136.8
155.6
NH O
O
3k
S23
-
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0
6.55
3.68
4.67
2.44
1.00
2.31
0.95
5.40
0.96
1.14
1.15
1.17
1.20
1.21
1.23
1.25
1.33
1.36
1.39
1.60
1.61
1.62
1.64
1.65
1.71
1.72
1.73
1.74
1.75
1.76
1.94
1.96
1.98
2.69
2.71
2.73
3.48
3.52
3.54
4.09
4.11
4.12
4.71
4.73
7.20
7.20
7.21
7.23
7.23
7.28
7.29
7.30
7.31
7.33
7.33
NH O
O
3l
S24
-
102030405060708090100110120130140150160
24.9
25.5
30.8
32.2
33.5
49.8
64.0
76.9
77.2
77.5
125.9
128.3
128.4
141.5
155.9
NH O
O
3l
S25
