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Original Articles

QUANTITATIVE STUDY OF THE NUCLEOPHILICITY OF THE THIOCARBONYL GROUP IN HETEROCYCLIC COMPOUNDS

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Pages 271-279 | Received 04 Dec 1973, Published online: 13 Dec 2006
 

Abstract

When the kinetic constants of reactions between alkyl iodides and a number of hetero-cyclic thiocarbonyl derivatives are measured in solvent acetone, the reactivity extends over three orders of magnitude. The increasing nucleophiliticy is found in the series:

Bulkiness of the alkyl group in the alkylating agent has little influence when compared to the pyridine case. A correlation is found between the nucleophilic polarization energy calculated with HMO approximation and the measured constants.

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