Changes in the SNAr reaction mechanism brought about by preferential solvation

Jazmín Alarcón-Espósito; Ricardo A. Tapia; Renato Contreras; Paola R. Campodónico

doi:10.1039/C5RA20779G

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Changes in the S_NAr reaction mechanism brought about by preferential solvation†

Jazmín Alarcón-Espósito,*^a Ricardo A. Tapia,^b Renato Contreras^a and Paola R. Campodónico*^c

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* Corresponding authors

^a Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653-Santiago, Chile
E-mail: jazminalarcon@ug.uchile.cl

^b Facultad de Química, Pontificia Universidad Católica de Chile, Código Postal 7820436, Santiago, Chile

^c Centro de Química Médica, Facultad de Medicina, Clínica Alemana, Universidad del Desarrollo, Código postal 771-0162, Santiago, Chile

Abstract

We herein report an experimental and theoretical study on preferential solvation effects for the reactions of 1-fluoro and 1-chloro-2,4-dinitrobenzene towards morpholine in acetonitrile, water and mixtures of them of varying compositions. A detailed kinetic study opens the possibility of analyzing preferential solvation and reaction rates. The kinetic study was complemented with an exploration of the potential energy surface in order to analyze the nature of the molecular interactions. For the fluorine derivative, this analysis reveals that the solvation of the TS in the mode TS1F-water/MeCN clearly outweighs the solvation of TS1F-MeCN/water, thereby suggesting that there is preferential solvation in favor of the aqueous phase.

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Article information

DOI: https://doi.org/10.1039/C5RA20779G
Article type: Paper
Submitted: 07 Oct 2015
Accepted: 08 Nov 2015
First published: 11 Nov 2015

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RSC Adv., 2015,5, 99322-99328

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Changes in the S_NAr reaction mechanism brought about by preferential solvation

J. Alarcón-Espósito, R. A. Tapia, R. Contreras and P. R. Campodónico, RSC Adv., 2015, 5, 99322 DOI: 10.1039/C5RA20779G

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