Interaction of Acetonitrile with Trifluoromethanesulfonic Acid: Unexpected Formation of a Wide Variety of Structures
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1 Interaction of Acetonitrile with Trifluoromethanesulfonic Acid: Unexpected Formation of a Wide Variety of Structures George E. Salnikov, Alexander M. Genaev*, Vladimir G. Vasiliev, and Vyacheslav G. Shubin Vorozhtsov ovosibirsk Institute of Organic Chemistry Academician Lavrent ev Ave., 9, ovosibirsk , Russian Federation genaev@nioch.nsc.ru Electronic Supplementary Information Table of content page page MeC-TfO (1:14 m/m), products and their chemical shifts Table 1 1 MR spectra, Me region 1 MR spectra, and C regions 13 C MR spectrum, 192 h at r.t. 19 F MR spectrum, 192 h at r.t correlations, 214 h at r.t. S2 S3 S4 S5 S6 S7 S8 MeC-TfO (4:1 m/m), products and their chemical shifts Table 3 1 MR spectra, C region 1 MR spectra, region 13 C MR spectrum, 214 h at r.t. ESI-MS spectra ESI-MS spectra (heavy ions) S19 S19 S20 S21 S22 S23 S25 MeC-TfO (1:2 m/m), products and their chemical shifts Table 2 1 MR spectra, C region 1 MR spectra, region 13 C MR spectrum, 316 h at r.t correlations, 316 h at r.t. C vs. CD 3 C, 1 MR spectra ESI-MS spectra MeC-TfO (1:1 m/m), products and their chemical shifts Table 4 1 and 13 C MR spectra S9 S10 S11 S12 S13 S14 S15 S16 S17 S17 S18 MeC-TfO (17:1 m/m), products and their chemical shifts Table 5 1 MR spectra, C region 1 MR spectra, region MeC-TfO (20:1 m/m), 1 MR spectrum 13 C MR spectrum MeC-TfO (200:1 m/m), 1 MR spectrum S26 S26 S27 S28 S29 S30 S31
2 S2 Chemical shifts of MeC, TfO (molar ratio 1:14) and of the products of their interaction. 1 chemical shifts are given in italics, 13 C in ordinary font, 15 in bold face. ere and further the chemical shifts of acetonitrile are in fact those of its mixture with the protonated form, the MR signals are averaged due to a rapid exchange d 2.0 C 21.6 J 0.9 z C Tf O TfO 1 J CF z 19 F F d 21.5 J 0.7 z O C C O C O O J CF 321 z Tf 19 F J F-F 0.85 z OTf J CF 320 z 4 J CF 1.1 z 19 F J FF 3.6 z Tf O CF 1 J CF 274 z 3 19 F J FF 3.6 z 6.44 d O 2.1 z O O 6.87 dq 2.1, 0.8 z C d O C O O O 6.80 q 0.7 z C d 0.7 z z s O 6.89 q z s O C d 1.0 z 19.9
3 Table 1. Products of the interaction of MeC with TfO (mol. ratio 1:14). Given in italics are logarithms of diffusion coefficients (m 2 /s) derived from the DOSY spectra. S3 Time (h) e MeC 1 а 2 а 3 а 4 а 5 а sum Tf 2 O b СF 3 OTf b DOSY F DOSY c /74º /74º /74º /74º DOSY d /74º /74º DOSY а Percentage of the acetonitrile turned into the corresponding product as determined from the 1 Н MR spectra. b Molar part (%) relative to the initial quantity of acetonitrile. c For TfO lg D = (from 19 F DOSY). d At 7 ºC. e In Fig. 1 of the paper an hour at 74 o C was set equal to 300 hours at room temperature
4 S4
5 S5
6 S6
7 S7
8 S8
9 Chemical shifts of MeC, TfO (molar ratio 1:2) and of the products of their interaction. 1 chemical shifts are given in italics, 13 C in ordinary font, 15 in bold face. S C F Tf O O Tf F OTf O C C C C C C C C C 3 14 C 3 4 O O O C
10 Table 2. Products of the interaction of MeC with TfO (mol. ratio 1:2). Given in italics are logarithms of diffusion coefficients (m 2 /s) derived from the DOSY spectra. S Time (h) MeC 12 а 1 а 13 а 11 а 4 а 14 а 3 а 15 а sum Tf 2 O b DOSY c DOSY а Percentage of the acetonitrile turned into the corresponding product as determined from the 1 Н MR spectra. b Molar part (%) relative to the initial quantity of acetonitrile. c At 7ºC.
11 S11
12 S12
13 S13
14 S14
15 S15 ESI-MS spectra
16 S16 MeC-TfO (1:2 m/m, 4000 h, 5 mg) in MeC (1 ml) FIA, MeC, 0.1ml/min, 4 µl, tune_low.m, ES Intens. x x MS, min #(28-31) (C3C)COC2, M+n, (C3C)3, M+n, x (C3C)3COC2, M+n, x (C3C)3(COC2)2, M+n, m/z
17 S17 Chemical shifts of MeC, TfO (molar ratio 1:1) and of the products of their interaction. 1 chemical shifts are given in italics, 13 C in ordinary font, 15 in bold face C F Tf O C C C 3 C C C 3 Table 4. Products of the interaction of MeC with TfO (mol. ratio 1:1). а Given in italics are logarithms of diffusion coefficients (m 2 /s) derived from the DOSY spectra. Time (h) MeC Sum DOSY а Percentage of the acetonitrile turned into the corresponding product as determined from the 1 Н MR spectra. 90.9
18 S18
19 Chemical shifts of MeC, TfO (molar ratio 4:1) and of the products of their interaction. 1 chemical shifts are given in italics, 13 C in ordinary font, 15 in bold face. S C F Tf O C C C C C C C C C C C C Table 3. Products of the interaction of MeC with TfO (mol. ratio 4:1). а Given in italics are logarithms of diffusion coefficients (m 2 /s) derived from the DOSY spectra. Time (h) MeC Sum MeC DOSY а Percentage of the acetonitrile turned into the corresponding product as determined from the 1 Н MR spectra.
20 S20
21 S21
22 S22
23 ESI-MS spectra S23 MeC-TfO (4:1 m/m, 5000 h, 5mg) in MeC (1 ml) FIA, MeC 0.1 ml/min, 2 µl, ES Intens. x x x x x x x MS, min #(29-34) (C3C)6, M+n, (MeC) (C3C)9, M+n, (C3C)9OSO2CF3, M+n, (C3C)12OSO2CF3, M+n, (C3C)12(OSO2CF3)2, M+n, (C3C)15(OSO2CF3)2, M+n, m/z
24 Intens. x10 4 +MS, min #(29-34) S (C3C)18(OSO2CF3)3, M+n, (C3C)18(OSO2CF3)4, M+n, (C3C)21(OSO2CF3)4, M+n, (C3C)24(OSO2CF3)5, M+n, m/z
25 S25 MeC-TfO (4:1 m/m, 5000 h, 5mg) in MeC (1 ml) FIA, MeC, 0.1 ml/min, 4 µl,, tune_high.m, ES eavy ions detection Intens MS, min #(26-40) (C3C)27(SO3CF3)6, M+n, (C3C)33(SO3CF3)8, M+n, (C3C)36(SO3CF3)8, M+n, m/z
26 1 chemical shifts of MeC, TfO (molar ratio 17:1, 34 h at r.t.) and of the products of their interaction. S C F Tf O d J 0.7 z 1.99 C O C C O C 1.96 C C 3 C 3 Table 5. Products of the interaction of MeC with TfO (mol. ratio 17:1, 1 M TfO). а Time (h) MeC acetamide + Sum MeC а Percentage of the acetonitrile turned into the corresponding product as determined from the 1 Н MR spectra.
27 S27
28 S28
29 S29
30 S30
31 S31
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