Benzimidazolium hydrogen nitroterephthalate

Abstract

In the title compound, C7H7N2+·C8H4NO6−, the partially overlapped arrangement and the shorter face‐to‐face distance of 3.457 (4) Å indicate π–π stacking between parallel benzimidazolium cations, whereas the longer face‐to‐face distance of 3.649 (6) Å suggests normal van der Waals contacts between parallel benzene rings of neighbouring nitro­terephthalate anions.

Crystal growth and physical properties of the organic salt benzimidazolium 3-nitrophthalate

“…(c) Benzimidazolium in 2-nitroterephthalate (CSD: HAYZAJ). 23 The interactions look more like that of pure benzimidazole. The absence of symmetry is caused by the fact that 2-nitroterephthalate is also present in the promolecule.…”

“…[19][20][21] It is said that carboxylic acid and benzimidazole nitrogen are the best donor and acceptor, respectively, for salt formation. The crystal structure of BZD with nitrosubstituted benzoic acid such as 3-and 4-nitrobenzoic acid 22 and derivatives such as nitroterephthalic acid, 23 2-nitrobenzoate bisIJ2-nitrobenzoic acid) 24 has been reported. The crystal structure of BZD with other proton donors such as 3-carboxy phenyl acetate, 25 chloranilic acid, 26 2,4,6trinitrophenol, 27 and 3,5-dicarboxylic acid [28][29][30] has been reported.…”

“…18 Phthalic acid, isophthalic acid and terephthalic acid are aromatic dicarboxylic acids and isomers of each other. In the crystal structure of BZD with nitro-substituted 2-terephthalic acid (BZD + •NTPh − ), 23 the benzimidazolium cation and the nitroterephthalate anion are linked to each other via N-H⋯O and O-H⋯O hydrogen bonding. The presence of the electron-withdrawing group -NO 2 in the isomers destabilizes the closest carboxylic acid on the benzene ring resulting in the loss of the proton to one of the nitrogens of BZD.…”

An imidazole-based organocatalyst designed for bulk polymerization of lactide isomers: inspiration from Nature

“…Benzimidazolium cations are known to be more acidic than imidazolium cations, 19 and they also suffer from p-p interactions due to their benzene rings. 20 In the case of a bifunctional mechanism such interaction may play an important role regarding their interaction with the L-LA monomer. Indeed, as already observed for protonated DBU, 15 (benz)imidazolium cations are believed to function as L-LA electrophilic activators.…”

Growth and Characterization of Benzimidazolium Salicylate: NLO Property from a Centrosymmetric Crystal

“…Hence it is widely used in the formation of organic molecular complex salts like benzimidazolium hydrogen phenylmalonate, benzimidazolium hydrogen nitroterepthalate, 2 methyl benzimidazolium picrate, and so forth [13][14][15]. According to Mulliken, the charge transfer interactions between two aromatic molecules arise due to the transfer of an electron from Lewis base to Lewis acid and have attracted considerable attention on these complexes for their nonlinear optical properties [16,17].…”