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Studies via X‐ray analysis on intermolecular interactions and energy frameworks based on the effects of substituents of three 4‐aryl‐2‐methyl‐1 H ‐imidazoles of different electronic nature and their in vitro antifungal evaluation
Author(s) -
Macías Mario A.,
Elejalde Nerith-Rocio,
Butassi Estefanía,
Zacchino Susana,
Portilla Jaime
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618014109
Subject(s) - substituent , imidazole , intermolecular force , aryl , chemistry , ring (chemistry) , crystal structure , polar effect , stereochemistry , medicinal chemistry , crystallography , alkyl , molecule , organic chemistry
The crystal structures of 2‐methyl‐4‐phenyl‐1 H ‐imidazole, C 10 H 10 N 2 , (3 a ), 4‐(4‐chlorophenyl)‐2‐methyl‐1 H ‐imidazole hemihydrate, C 10 H 9 ClN 2 ·0.5H 2 O, (3 b ), and 4‐(4‐methoxyphenyl)‐2‐methyl‐1 H ‐imidazole, C 11 H 12 N 2 O, (3 c ), 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 (3 a ), Cl in (3 b ) and OMe in (3 c ), the formation of strong N—H…N connections has the probability (3 a ) > (3 b ) > (3 c ), while compound (3 c ) proves to be more active than (3 a ) and (3 b ) at all concentrations against C. neoformans .