Synthesis and crystal structures of two 1H-benzo[d]imidazole derivatives: DFT and anticorrosion studies, and Hirshfeld surface analysis

The title benzimidazole compounds, namely, 2-(4-methoxynaphthalen-1-yl)-1H-benzo[d]imidazole, C18H14N2O (I) and 2-(4-methoxynaphthalen-1-yl)-1-[(4-methoxynaphthalen-1-yl)methyl]-1H-benzo[d]imidazole ethanol monosolvate, C30H24N2O2 · C2H6O (II), were synthesized by the condensation reaction of benzene-1,2-diamine with 4-methoxynaphthalene-1-carbaldehyde in the ratios 1:1 and 1:2, respectively. In I, the mean plane of the naphthalene ring system is inclined to that of the benzimidazole ring by 39.22   (8) ° , while in II, the corresponding dihedral angle is 64.76   (6) ° . This difference is probably influenced by the position of the second naphthalene ring system in II; it is inclined to the benzimidazole ring mean plane by 77.68   (6) ° . The two naphthalene ring systems in II are inclined to one another by 75.58   (6) ° . In the crystal of I, molecules are linked by N — H...N hydrogen bonds to form chains propagating along the a-axis direction. Inversion-related molecules are also linked by a C — H... π interaction linking the chains to form layers lying parallel to the ac plane. In the crystal of II, the disordered ethanol molecule is linked to the molecule of II by an O — H...N hydrogen bond. There are a number of C — H... π interactions present, both intra- and intermolecular. Molecules related by an inversion centre are linked by C — H... π interactions, forming a dimer. The dimers are linked by further C — H... π interactions, forming ribbon...

Source: Acta Crystallographica Section C - June 29, 2023 Category: Chemistry Authors: Ghichi, N. Djedouani, A. Hannachid, D. Elhadi, S.M. Benboudiaf, A. Merazig, H. Ouksel, L. Hellal, A. Stoeckli-Evans, H. Tags: benzo[d]imidazole 4-methoxynaphthalene hydrogen bonding crystal structure Hirshfeld surfaces DFT calculations anticorrosion research papers Source Type: research