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A Kinetic Investigation of Regioselective Solvation of a Solvatochromic Dye in Aqueous Alcohols
Author(s) -
Domínguez Moisés,
Machado Vanderlei Gageiro,
Nandi Leandro Guarezi,
Rezende Marcos Caroli,
Silva Patricia
Publication year - 2015
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.20963
Subject(s) - solvatochromism , chemistry , solvation , reactivity (psychology) , methanol , aqueous solution , kinetics , ethanol , kinetic energy , photochemistry , alcohol , regioselectivity , organic chemistry , computational chemistry , solvent , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics
The kinetics of methylation of the solvatochromic dye 4‐[(2,4‐dinitrobenzyli‐dene)imino]‐2,6‐diphenylphenolate by dimethyl sulfate was investigated in three aqueous alcohols (1‐propanol, ethanol, and methanol), in the search of a sharp change in its reactivity in water‐rich media. The observed kinetic results paralleled previous observations of a sharp change in the solvatochromic behavior of the dye in the same media and was supported by a QM/MM simulation of the dye in two methanol–water mixtures, which rationalized the observed sharp change in the phenolate reactivity.

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