H-bond and dipole–dipole interactions between water and COO functional group in methyl benzoate derivatives: Substituent and heteroatom effects |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan;2. Faculty of Pharmacy, Department of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan;3. Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan;1. Materials Science Laboratory, Department of Physics, Periyar University, Salem, Tamil Nadu, 636011, India;2. Department of Physics, ERK College of Arts and Science, Dharmapuri, Tamil Nadu, 636905, India;1. School of Physics and Electronics, Shandong Normal University, Jinan 250014, China;2. School of Biological Sciences, Nanyang Technological University, Singapore 639815, Singapore;3. School of Chemistry, Shandong Normal University, Jinan 250014, China;1. CSIR-Central Food Technological Research Institute, Resource Centre Lucknow, 226018 India;2. Public Health Foundation of India, Plot 47, Sector 44, Gurgaon 122002 National Capital Region, India |
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| Abstract: | Interactions of COOCH3 functional group of methyl benzoate (MB) and its derivatives can substantially be affected by substituents and heteroatoms. The substituent and heteroatom effects on the intermolecular interactions in the complexes of MB and its derivatives with the water molecule have been investigated by the quantum mechanical calculations in the present study. Electron donating (ED)/electron withdrawing (EW) substituents increase/decrease the binding energy (ΔEbin) between mentioned functional group and hydrogen bond donor, and the N heteroatom in the six membered ring weakens the effect. The effects of the N heteroatoms depend on their positions in the ring, and the effects of substituents depend on the number and the positions of heteroatoms. Some relations were obtained between the dipole moment of carbonyl group, results obtained from the natural bond orbital (NBO) and the atoms in molecules (AIM) analysis, binding energy and Hammett constants of substituents. The results can be used to predict the factors affect the intermolecular interactions, and to improve the ligand-protein bindings in biological systems. |
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| Keywords: | Methyl benzoate Methyl nicotinate Methyl picolinate Drug design Ab initio method Population analysis |
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