Substituent effect on the electron acceptor property of 1,4-benzoquinone towards the formation of molecular complex with sulfamethoxazole
| Autor: | Kuppanagounder P. Elango, A. Satheshkumar, K. Ganesh, C. Balraj |
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| Rok vydání: | 2013 |
| Předmět: |
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Molecular chemistry.chemical_classification Magnetic Resonance Spectroscopy Sulfamethoxazole Ab initio Substituent Nuclear magnetic resonance spectroscopy Electron acceptor Electrochemistry Photochemistry Mass Spectrometry Atomic and Molecular Physics and Optics Analytical Chemistry Quinone 1 4-Benzoquinone chemistry.chemical_compound Anti-Infective Agents chemistry Spectroscopy Fourier Transform Infrared Benzoquinones Proton NMR Spectrophotometry Ultraviolet Instrumentation Spectroscopy |
| Zdroj: | Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 107:156-166 |
| ISSN: | 1386-1425 |
| DOI: | 10.1016/j.saa.2013.01.016 |
| Popis: | UV-Vis, (1)H NMR, FT-IR, LC-MS and fluorescence spectral techniques were employed to investigate the mechanism of interaction of sulfamethoxazole with varying number of methoxy/chloro substituted 1,4-benzoquinones (MQ1-4) and to characterize the reaction products. The interactions of MQ1-4 with sulfamethoxazole (SULF) were found to proceed through the formation of a donor-acceptor complex, containing radical anion and its conversion to the product. Fluorescence quenching studies showed that the interaction between the donor and the acceptors are spontaneous. The results indicated that the progressive replacement of chlorine atom (-I effect) by methoxy group (+M effect) in the quinone decreased the electron acceptor property of the quinone. The results of the correlation of experimentally measured binding constants with electrochemical data and ab initio DFT calculations supported these observations. |
| Databáze: | OpenAIRE |
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