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 ribbons propagating along the b-axis direction. The interatomic contacts in the crystal structures of both compounds were explored using Hirshfeld surface analysis. The molecular structures of I and II were determined by density functional theory (DFT) calculations at the M062X/6-311+g(d) level of theory and compared with the experimentally determined molecular structures in the solid state. Local and global reactivity descriptors were computed to predict the reactivity of the title compounds. Both compounds were shown to exhibit significant anticorrosion properties with respect to iron and copper.

中文翻译：

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两种1H-苯并[d]咪唑衍生物的合成和晶体结构：DFT和防腐研究以及赫什菲尔德表面分析

标题苯并咪唑化合物，即2-(4-甲氧基萘-1-基)-1H-苯并[ d ]咪唑，C ₁₈ H ₁₄ N ₂ O( I )和2-(4-甲氧基萘-1-基)通过缩合反应合成-1-[(4-甲氧基萘-1-基)甲基]-1 H-苯并[ d ]咪唑乙醇单溶剂合物C ₃₀ H ₂₄ N ₂ O ₂ ·C ₂ H ₆ O ( II ) 1,2-苯二胺与4-甲氧基萘-1-甲醛分别以1:1和1:2的比例反应。在我，萘环系的平均平面与苯并咪唑环的平均平面倾斜39.22（8）°，而在II中，相应的二面角为64.76（6）°。这种差异可能是受到II中第二个萘环系统的位置的影响；它与苯并咪唑环平均平面倾斜77.68(6)°。II中的两个萘环系彼此倾斜 75.58 (6)°。在I的晶体中，分子通过 N—H…N 氢键连接，形成沿 a轴方向传播的链。与反转相关的分子也通过 CH…π 相互作用连接，将链连接起来形成平行于ac平面的层。在水晶中II ，无序乙醇分子通过OH…N氢键与II分子连接。存在许多分子内和分子间的 C—H…π 相互作用。由反转中心相关的分子通过CH…π相互作用连接，形成二聚体。二聚体通过进一步的 C—H…π 相互作用连接，形成沿b轴方向传播的带。使用赫什菲尔德表面分析探索了两种化合物晶体结构中的原子间接触。I和II的分子结构通过 M062X/6-311+g(d) 理论水平的密度泛函理论 (DFT) 计算确定，并与实验确定的固态分子结构进行比较。计算局部和全局反应性描述符以预测标题化合物的反应性。这两种化合物都对铁和铜表现出显着的防腐性能。