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Crystal structure and synthesis of benzimidazole substituted acrylonitriles and benzimidazo[1,2-a]quinolines (CROSBI ID 146248)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Hranjec, Marijana ; Pavlović, Gordana ; Karminski-Zamola, Grace Crystal structure and synthesis of benzimidazole substituted acrylonitriles and benzimidazo[1,2-a]quinolines // Structural chemistry, 20 (2009), 1; 91-99. doi: 10.1007/s11224-008-9398-4

Podaci o odgovornosti

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

engleski

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

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.

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

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Podaci o izdanju

20 (1)

2009.

91-99

objavljeno

1040-0400

1572-9001

10.1007/s11224-008-9398-4

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Kemija

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