Related Experiment Video
Updated: May 5, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
The thiomethyl anion: Formation, reactivity, and thermodynamic properties
1Department of Chemistry, University of Minnesota, 55455, Minneapolis, MN.
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.
More Related Videos
Related Concept Videos
Preparation and Reactions of Thiols
Structure and Nomenclature of Thiols and Sulfides
Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics
Radical Halogenation: Thermodynamics
π Molecular Orbitals of the Allyl Cation and Anion
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

