The thiomethyl anion: Formation, reactivity, and thermodynamic properties

Steven R. Kass; Hangzhou Guo; Gregg D. Dahlke

doi:10.1016/1044-0305(90)85016-F

The thiomethyl anion: Formation, reactivity, and thermodynamic properties

Steven R. Kass
, Hangzhou Guo
, Gregg D. Dahlke

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	366-371
Number of pages	6
Journal	Journal of the American Society for Mass Spectrometry
Volume	1
Issue number	5
DOIs	https://doi.org/10.1016/1044-0305(90)85016-F
State	Published - Sep 1990

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title = "The thiomethyl anion: Formation, reactivity, and thermodynamic properties",

abstract = "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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AU - Dahlke, Gregg D.

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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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The thiomethyl anion: Formation, reactivity, and thermodynamic properties

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