Issue 23, 1989

The gas-phase basicity and H/D exchange characteristics of the parent thiocarbonyl enolate anions

Abstract

The enethiolate anions corresponding to thioacetaldehye and thioacetone, synthesized via elimination reactions, undergo H/D exchange reactions, demonstrating the intermediacy of the thiocarbonyl tautomers, and proton transfer reactions, leading to ΔGacid0[CH3CH[double bond, length half m-dash]S]= 341 ± 3 kcal mol–1 and ΔGacid0[(CH3)2C[double bond, length half m-dash]S]= 344 ± 3 kcal mol–1(1 kcal = 4.184 KJ).

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1989, 1819-1821

The gas-phase basicity and H/D exchange characteristics of the parent thiocarbonyl enolate anions

L. Zhang and J. J. Grabowski, J. Chem. Soc., Chem. Commun., 1989, 1819 DOI: 10.1039/C39890001819

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