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Reactions of aryl acetates with secondary alicyclic amines in ethanol/water mixtures: Effect of the solvent composition on the kinetics and mechanism
Author(s) -
Castro Enrique A.,
Millan Daniela,
Aguayo Raul,
Campodónico Paola R.,
Santos José G.
Publication year - 2011
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20598
Subject(s) - alicyclic compound , chemistry , solvent , solvation , kinetics , ethanol , concerted reaction , organic chemistry , reaction mechanism , aryl , solvent effects , composition (language) , computational chemistry , catalysis , alkyl , physics , quantum mechanics , linguistics , philosophy
We report a kinetic study on the reactions of secondary alicyclic amines toward 4‐nitrophenyl, 2,4‐dinitrophenyl, and 2,4,6‐trinitrophenyl acetates ( 1, 2 , and 3 ) in ethanol/water mixtures of different compositions. It is found that (i) the intermediate in the reaction of 1 is stabilized in a mixture of 90 vol% ethanol; (ii) for the reaction of 2 , the mechanism is stepwise in water but concerted in the mixtures; (iii) For the reaction of 3 , the mechanism is concerted along the whole range of composition; (iv) the effect of NO 2 outweighs the solvent effect; (v) preferential solvation in the core of reaction can be ruled out. © 2011 Wiley Periodicals, Inc. Int J Chem Kinet 43: 687–693, 2011
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