Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions
Date
2014
Type:
Artículo
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1
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Journal Title
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Volume Title
Publisher
Royal Society of Chemistry
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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, by enhancing the electrophilicity of the pyrimidine moiety and the nucleophilicity of the nitrogen atom of the benzohydrazide fragment. The electronic mechanism can therefore be described as a (non-local) site activation problem.
Description
Centro de Química Médica
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Citation
RSC Adv., 2014,4, p:30638-30643
Keywords
SNAr reactions, Química, intramolecular hydrogen