H-bond and dipole-dipole interactions between water and COO functional group in methyl benzoate derivatives: Substituent and heteroatom effects

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• 作者：S. Sarhadinia ; A. Ebrahimi ; ^{ebrahimi@chem.usb.ac.ir}
• 关键词：Methyl benzoate ; Methyl nicotinate ; Methyl picolinate ; Drug design ; Ab initio method ; Population analysis
• 刊名：Journal of Molecular Graphics and Modelling
• 出版年：2016
• 出版时间：November 2016
• 年：2016
• 卷：70
• 期：Complete
• 页码：7-13
• 全文大小：852 K
• 卷排序：70

文摘

Although the replacement of nitrogen heteroatoms in six membered ring and the electron withdrawing substituents increase the dipole moment of carbonyl group, both changes decrease the binding energies. Replacement of the first nitrogen heteroatom in each position decreases the binding energy, while the second heteroatom weakness the effect of the former. Although the effect of substituents on Vmin value around the COO functional group is higher at the para position, the effect of nitrogen heteroatom is higher at the meta position. Resonance is dominant among the substituent effects, while electrostatic is dominant among the heteroatom effects.