Theoretical Investigations of Hydrogen Bonding Interactions of (E)-1-(1H-Benzo[d]imidazol-2-yl)-3-Phenylprop-2-en-1-one Momoners and Dimers: NBO, QTAIM and NCI Study
Modern Chemistry
Volume 7, Issue 4, December 2019, Pages: 80-94
Received: Aug. 19, 2019; Accepted: Sep. 16, 2019; Published: Oct. 9, 2019
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Adenidji Ganiyou, Training and Research Unit of Sciences of Structures, Matter and Technology (UFR SSMT), Laboratory of Organic Chemistry and Natural Substances, Félix Houphouët-Boigny University, Abidjan, Côte d'Ivoire
Kicho Denis Yapo, Training and Research Unit of Sciences of Structures, Matter and Technology (UFR SSMT), Laboratory of Organic Chemistry and Natural Substances, Félix Houphouët-Boigny University, Abidjan, Côte d'Ivoire
Doumadé Zon, Training and Research Unit of Sciences of Structures, Matter and Technology (UFR SSMT), Laboratory of Organic Chemistry and Natural Substances, Félix Houphouët-Boigny University, Abidjan, Côte d'Ivoire; Department of Biochemistry-Genetics, Training and Research Unit in Biological Science, Peleforo Gon Coulibaly University, Korhogo, Côte-d’Ivoire
Mamadou Guy-Richard Kone, Faculty of Fundamental and Applied Sciences (UFR SFA), Laboratory of Thermodynamics and Physico-Chemistry of the Middle, Nangui Abrogoua University, Abidjan, Côte d'Ivoire
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Hydrogen bonding is an essential interaction in nature and plays a crucial role in many formations of materials and biological processes, requiring a deeper understanding of its formation. Benzimidazole is an important structural unit found in a large number of natural and pharmacologically active molecules. In the present work, the electronic structures and properties and relatives stabilities of a series of (E)-1-(1H-benzo[d]imidazol-2-yl)-3-phenylprop-2-en-1-one monomers and dimers have been studied by density functional theory using B3LYP 6-31+G (d, p) calculation level. the strengths of the noncovalent interactions have been analyzed in terms of the QTAIM analysis, NCI analysis and natural bond orbital approaches. It was found that the dimers are formed by double N-H⋯O hydrogen bond. QTAIM analysis proved the presence of intramolecular hydrogen bond in monomers and coexistence of intramolecular and intermolecular hydrogen bond in dimers. Frequency analysis show that intermolecular N-H⋯O interactions are proper hydrogen bond while intramolecular C-H⋯N, C-H⋯O, C-H⋯H-C interactions are improper hydrogen bond. NBO and NCI analyses confirm the existence of hydrogen bonds in the studied monomers and dimers. The presence of weakly electron acceptor group on benzene ring favor the total interaction energy of dimerization.
NBO, QTAIM, NCI, Benzimidazole, Electron Density, Hydrogen Bond
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Adenidji Ganiyou, Kicho Denis Yapo, Doumadé Zon, Mamadou Guy-Richard Kone, Theoretical Investigations of Hydrogen Bonding Interactions of (E)-1-(1H-Benzo[d]imidazol-2-yl)-3-Phenylprop-2-en-1-one Momoners and Dimers: NBO, QTAIM and NCI Study, Modern Chemistry. Vol. 7, No. 4, 2019, pp. 80-94. doi: 10.11648/
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