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A combined computational and experimental approach for investigating a hydrogen‐bonded supermolecular compound comprising benzimidazole and malonic acid
Author(s) -
Jian FangFang,
Zhao PuSu,
Li YuFeng,
Wang Xian,
Yu Qing
Publication year - 2007
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21511
Subject(s) - tetramer , chemistry , hydrogen bond , benzimidazole , supramolecular chemistry , crystallography , infrared spectroscopy , density functional theory , malonic acid , crystal structure , computational chemistry , molecule , organic chemistry , enzyme
A hydrogen‐bonded tetramer supramolecular motif of 2:2 benzimidazole (BIZ) and malonic acid (MLA) has been synthesized and characterized by elemental analysis, infrared (IR), and X‐ray single crystal diffraction. Thermal stability analyses demonstrate that this supramolecular adduct is a new material and it is not the ordinary superposition of the original monomers. Density function theory (DFT) calculations for the models of dimers, trimers, and tetramer comprising BIZ and MLA have been carried out at B3LYP/6‐31G* and PBE1PBE/6‐31G* levels of theory, respectively. By comparing the calculated results with the experiments (single crystal structure, IR spectra, and thermal analysis) and based on the statistic thermodymnamic calculations, it is concluded that the dimers cannot exist at room temperature and the tetramer can simulate the title supramolecular complex better than the two trimers. Further studies on the model of tetramer indicate that the hydrogen bond of N···HO is stronger than that of O···HN. © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2008