Research Article: Involvement of conformational isomerism in the complexity of the crystal network of 1-(4-nitro­phen­yl)-1H-1,3-benzimidazole derivatives driven by C—H⋯A (A = NO2, Npy and π) and orthogonal Npy⋯NO2 and ONO⋯Csp2 inter­actions

Date Published: April 01, 2018

Publisher: International Union of Crystallography

Author(s): Mónica I. García-Aranda, Carlos Z. Gómez-Castro, Efrén V. García-Báez, Yolanda Gómez y Gómez, José L. Castrejón-Flores, Itzia I. Padilla-Martínez.


Participation of π– and n–π* (n = O and Npy; π* = Csp2 and ) inter­actions in the equi-energetic conformations of 1-(4-nitro­phen­yl)-1H-1,3-benzimidazoles.

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Benzimidazoles are recognized as essential chemical motifs present in a variety of natural products, agrochemicals and bioactive mol­ecules (Keri et al., 2015 ▸). Particularly, C2-aryl-substituted benzimidazoles are often found as a key unit in various natural compounds, biologically active agents, potent pharmacophores and functional chemicals (Horton et al., 2003 ▸; Kumar, 2004 ▸; Candeias et al., 2009 ▸; Gupta & Rawat, 2010 ▸; Carvalho et al., 2011 ▸). In addition, N-aryl­benzimidazoles are a class of prominent heterocyclic compounds that exhibit a wide range of biological properties (Sabat et al., 2006 ▸; Elias et al., 2011 ▸). In particular, 1,2-di­aryl­benzimidazoles have been reported as strong inhibitors of human cyclo­oxygenases with a skewed selectivity towards the COX-2 (cyclooxygenase 2) isoform at the micromolar level (Secci et al., 2012 ▸).




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