TY - JOUR
T1 - The thiomethyl anion
T2 - Formation, reactivity, and thermodynamic properties
AU - Kass, Steven R.
AU - Guo, Hangzhou
AU - Dahlke, Gregg D.
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 1990/9
Y1 - 1990/9
N2 - The thiomethyl anion (1) has been generated by fluorodesilylation of trimethylsilylmethanethiol in a variable-temperature flowing afterglow device. The proton affinity (1649 ± 12 kJ mol-1) and electron affinity (0.67 ± .13 eV) were determined and compared to a previously reported molecular orbital calculation. Isomerization via a 1,2-proton shift does not take place between -40° and 100°C despite a 156 kJ mol-1 driving force. Ion-molecule reactions of 1 were examined with a number of reagents including N20, O2, CS2, COS, and CO2, Hydride ion transfer was observed in every case, along with other products, and thermodynamic information has been derived.
AB - The thiomethyl anion (1) has been generated by fluorodesilylation of trimethylsilylmethanethiol in a variable-temperature flowing afterglow device. The proton affinity (1649 ± 12 kJ mol-1) and electron affinity (0.67 ± .13 eV) were determined and compared to a previously reported molecular orbital calculation. Isomerization via a 1,2-proton shift does not take place between -40° and 100°C despite a 156 kJ mol-1 driving force. Ion-molecule reactions of 1 were examined with a number of reagents including N20, O2, CS2, COS, and CO2, Hydride ion transfer was observed in every case, along with other products, and thermodynamic information has been derived.
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U2 - 10.1016/1044-0305(90)85016-F
DO - 10.1016/1044-0305(90)85016-F
M3 - Article
C2 - 24248898
AN - SCOPUS:0001371611
SN - 1044-0305
VL - 1
SP - 366
EP - 371
JO - Journal of the American Society for Mass Spectrometry
JF - Journal of the American Society for Mass Spectrometry
IS - 5
ER -