Author:
Macías Mario A.,Elejalde Nerith-Rocio,Butassi Estefanía,Zacchino Susana,Portilla Jaime
Abstract
The crystal structures of 2-methyl-4-phenyl-1H-imidazole, C10H10N2, (3a), 4-(4-chlorophenyl)-2-methyl-1H-imidazole hemihydrate, C10H9ClN2·0.5H2O, (3b), and 4-(4-methoxyphenyl)-2-methyl-1H-imidazole, C11H12N2O, (3c), have been analyzed. It was found that the electron-donating/withdrawing tendency of the substituent groups in the aryl ring influence the acid–base properties of the 2-methylimidazole nucleus, changing the strength of the intermolecular N—H...N interactions. This behaviour not only influences the crystal structure but also seems to have an important effect on the antifungal activity. Considering the substituent groups, that is, H in (3a), Cl in (3b) and OMe in (3c), the formation of strong N—H...N connections has the probability (3a) > (3b) > (3c), while compound (3c) proves to be more active than (3a) and (3b) at all concentrations against C. neoformans.
Funder
Department of Chemistry and Vicerrectoría de Investigaciones
Agencia Nacional de Promoción Científica y Tecnológica
Publisher
International Union of Crystallography (IUCr)
Subject
Materials Chemistry,Inorganic Chemistry,Physical and Theoretical Chemistry,Condensed Matter Physics
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