Sulfur isotope effects in substitution reactions of trimethylsulfonium ion

Autor:	Ronald T. Hargreaves, William H. Saunders, Arthur M. Katz
Rok vydání:	1976
Předmět:	Substitution reaction Ethanol Dimethyl sulfoxide Inorganic chemistry General Chemistry Trimethylsulfonium Biochemistry Medicinal chemistry Catalysis Chemical kinetics chemistry.chemical_compound Colloid and Surface Chemistry Nucleophile chemistry Bromide Kinetic isotope effect
Zdroj:	Journal of the American Chemical Society. 98:2614-2617
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00425a034
Popis:	Sulfur isotope effects were determined for the SN/sub 2/ reactions in ethanol at 60/sup 0/C of trimethylsulfonium ion with bromide, thiophenoxide, ethoxide, and phenoxide. The effects were 1.36, 1.20, 0.96, and 0.96 percent, respectively. The isotope effect with ethoxide in ethanol decreased upon addition of dimethyl sulfoxide. The decrease was almost linear with mole percent dimethyl sulfoxide, reaching a value of 0.35 percent at 65 percent dimethyl sulfoxide. These results suggest that the basicity of the attacking nucleophile is the most important factor in determining the extent of carbon-sulfur cleavage in the transition state.
Databáze:	OpenAIRE
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