Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions-Reference-Cited by-同舟云学术

Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions

Published:2014 Issue:58 Volume:4 Page:30638-30643
ISSN:2046-2069
Container-title:RSC Adv.
language:en
Short-container-title:RSC Adv.

Author:

Gallardo-Fuentes Sebastián¹²³⁴,Tapia Ricardo A.⁵⁶⁷,Contreras Renato¹²³⁴,Campodónico Paola R.⁸⁹¹⁰⁴

Affiliation:

1. Departamento de Química

2. Facultad de Ciencias

3. Universidad de Chile

4. Santiago, Chile

5. Facultad de Química

6. Pontificia Universidad Católica de Chile

7. Santiago 6094411, Chile

8. Centro de Química Médica

9. Facultad de Medicina

10. Clínica Alemana Universidad del Desarrollo

Abstract

The nucleophilic aromatic substitution reaction of benzohydrazide derivatives towards 2-chloro-5-nitropyrimidine is used as model system to experimentally and theoretically show that intramolecular hydrogen-bond formation operates as a perturbation that elicits a dual response at the reaction center of the transition state (TS) structure.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2014/RA/C4RA04725G

Reference24 articles.

1. The ortho: para Ratio in Activation of Aromatic Nucleophilic Substitution by the Nitro Group1

2. 85. Nucleophilic displacement reactions in aromatic systems. Part I. Kinetics of the reactions of chloronitropyridines with aromatic amines and with pyridine

3. Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an “Inverted Built-In Solvation” Be Responsible for the Peculiar Activation by an o-Carboxamido Group in SNAr Reactions with an Anionic Nucleophile?

4. Ortho selectivity in SNAr substitutions of 2,4-dihaloaromatic compounds. Reactions with piperidine

5. Evidences for the Key Role of Hydrogen Bonds in Nucleophilic Aromatic Substitution Reactions

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