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Solvent effects in the reaction of 2‐thiophenesulfonyl chloride with aniline
Author(s) -
Arcoria Antonino,
Maccarone Emanuele,
Tomaselli Gaetano A.,
Calí Rosario,
Currieri Salvatore
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120224
Subject(s) - chemistry , aniline , reaction rate constant , acetonitrile , solvent , methanol , acetone , solvent effects , reaction rate , entropy of activation , inorganic chemistry , ethanol , chloride , medicinal chemistry , photochemistry , organic chemistry , catalysis , kinetics , physics , quantum mechanics
The second order rate constants k 2 and the activation parameters for the reaction of 2‐thiophenesulfonyl chloride with aniline together with solution enthalpies of the reactants have been measured in methanol, ethanol, 2‐propanol, acetonitrile and acetone. The reaction rates are slower in dipolar aprotic solvents than in protic ones due to a remarkable activation negative entropy. The rate constants k 2 are correlated with empirical solvent polarity parameters. The data seem in accord with a S A N reaction mechanism.