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Acidity of organic sulfides

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Theoretical and Experimental Chemistry Aims and scope

Abstract

The rate of base-catalyzed hydrogen exchange (bases KNH2 in NH3. t-C4H3OK in t-C4H3OH) has been used to mesure the acidity of sulfides RSCD3, in which R is CH3, C6H6, C6H11, or C5H8, The cycloalkyli are found to act as electron acceptors. The effects of one and two CH8 and SC6H6 are examined. The sulfides are compered with hydrocarbons and also with 3CH3, OCH1 and NCH3 attached to benzene. The vacant 3d levels of the sulfur stabilize the sulfide carbanions; deuterium exchange shows that the charge distribution ir.p-dimethylaminothiazole is due to pd conjugations. Synthesis routes are described for compounds tagged with deuterium in specified positions: C6H11SCD3, C6H8SCD1, C6H5SCD1CH3, C6H3SCD(CH3)2, p-(CH3)2NC5H4SCD3, and p-(CD3)2NC5H4SCH3.

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Authors and Affiliations

  1. Karpov Institute of Physical Chemistry, Moscow

    A. I. Shatenshtein & E. A. Gvozdeva

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  1. A. I. Shatenshtein
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  2. E. A. Gvozdeva
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Shatenshtein, A.I., Gvozdeva, E.A. Acidity of organic sulfides. Theor Exp Chem 1, 226–232 (1965). https://doi.org/10.1007/BF01134325

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