The kinetics of the reaction of some 4-substituted 2-nitrochlorobenzenes with toluene-p-thiolate in dimethylformamide have been measured at temperatures from -39.7 to 71.9°C. Correlation of rates by Hammett-type equations gives, using the best set of σ values, ρ = +6.65 at 10°C. The dependence of the ρ value on the solvent is discussed. A comparison of these reactions with those of Ar2C=CHCl and of ArC≡CCl with the same nucleophile-solvent system shows that the substituent effects are markedly attenuated by the interposition of C=C or C≡C bonds.

Kinetics of aromatic nucleophilic substitution by toluene-p-thiolate in dimethylformamide. Effect of solvent on Hammett-type correlations / P. Carniti, P. Beltrame, S. Cabiddu. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - 1973:10(1973), pp. 1430-1433.

Kinetics of aromatic nucleophilic substitution by toluene-p-thiolate in dimethylformamide. Effect of solvent on Hammett-type correlations

P. Carniti;P. Beltrame;
1973

Abstract

The kinetics of the reaction of some 4-substituted 2-nitrochlorobenzenes with toluene-p-thiolate in dimethylformamide have been measured at temperatures from -39.7 to 71.9°C. Correlation of rates by Hammett-type equations gives, using the best set of σ values, ρ = +6.65 at 10°C. The dependence of the ρ value on the solvent is discussed. A comparison of these reactions with those of Ar2C=CHCl and of ArC≡CCl with the same nucleophile-solvent system shows that the substituent effects are markedly attenuated by the interposition of C=C or C≡C bonds.
Settore CHIM/02 - Chimica Fisica
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/199072
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