Naslov
Crystal structure and synthesis of benzimidazole substituted acrylonitriles and benzimidazo[1,2-a]quinolines

Autori
Hranjec, Marijana ; Pavlović, Gordana ; Karminski-Zamola, Grace

Izvornik
Structural chemistry (1040-0400) 20 (2009), 1; 91-99

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
benzimidazole substituted acrylonitriles ; benzimidazo[1 ; 2-a]quinolines

Sažetak
The benzimidazole compounds and benzoannulated cyclic benzimidazole analogues, such as benzimidazo[1, 2-a]quinolines, are a part of our wider investigation on biologically active compounds, potential antitumor smart drugs. Here, we present the synthesis of two compounds, [2-(1H-benzimidazol-2-yl)-3-(4-bromophenyl)- acrylonitrile, 5] and [2-bromo-benzimidazo[1, 2-a]quinoline-6-carbonitrile, 7] and their crystal structures revealed by X-ray single crystal diffractometry. We also report the molecular and crystal structures of two additional compounds [2-(1H-benzimidazol-2- yl)-3-(4-cyanophenyl)-acrylonitrile, 4] and [benzimidazo[1, 2-a]quinoline-2, 6- dicarbonitrile, 6], which synthesis and spectroscopic characterization have been published earlier by us, too [26]. The compounds 4 and 5 crystallize as monohydrates. The dihedral angles calculated between phenyl and benzimidazole ring reflect not significant deviation from molecular planarity in the crystalline state for 4 and 5, while benzoannulated cyclic benzimidazole derivatives 6 and 7 are essentially planar. The crystal structures of 4 and 5 are characterized by O-H· ; ; N and N-H· ; ; O hydrogen bonds between water molecule of crystallization and imidazole NH group as well as CN group, while in 6 and 7 only weak C-H· ; ; N intermolecular hydrogen bonds exist. Although, crystal packings are analogous in 4 and 5, the molecular conformations differ slightly. In 6 there is one C-H· ; ; N hydrogen bond that do not exist in 7.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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