| Computational Study on OH Addition Reactions of Three Sulfonamides in Aqueous Solution |
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| 引用本文： | 曾小兰,孙小孜,王贺宇,于永生. Computational Study on OH Addition Reactions of Three Sulfonamides in Aqueous Solution[J]. 结构化学, 2020, 39(1): 48-56. DOI: 10.14102/j.cnki.0254-5861.2011-2509 |
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| 作者姓名： | 曾小兰 孙小孜 王贺宇 于永生 |
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| 作者单位： | College of Chemistry and Chemical Engineering |
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| 基金项目： | This project was supported by the National Natural Science Foundation of China;and Nanhu Scholars Program for Young Scholars of XYNU;Science and Technology Program of Henan Province |
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| 摘 要： | OH addition reactions of cationic,neutral and anionic forms of three sulfonamides(sulfamethoxazole,sulfadiazine and sulfapyridine)in aqueous solution were theoretically studied using density functional theory(DFT)method at the M06-2X/6-311+G(3df,2p)level.Transition state theory was applied to estimate the secondary rate constants for these elementary reactions.The obtained results indicate that OH addition reactions of sulfonamides can take place spontaneously at standard conditions.The anionic form of three sulfonamides has the highest addition activity,while the corresponding cationic form is the most inactive addition reagent.The benzene ring of neutral forms of three sulfonamides is always a more favorable site for OH radical addition than the oxazole,pyrimidine or pyridine ring.C(3)or(and)C(5)atoms of benzene ring are the most favorable positions for OH addition occurring in benzene ring.Although the water solvent has no remarkable effect on OH addition reactions of neutral sulfonamides,it exerts a significant adverse influence on OH addition reactions of ionic sulfonamides.
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| 关 键 词： | addition reaction SULFONAMIDE OH RADICALS REACTIVITY order position SELECTIVITY |
Computational Study on OH Addition Reactions of Three Sulfonamides in Aqueous Solution |
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| ZENG Xiao-Lan,SUN Xiao-Zi,WANG He-Yu,YU Yong-Sheng. Computational Study on OH Addition Reactions of Three Sulfonamides in Aqueous Solution[J]. Chinese Journal of Structural Chemistry, 2020, 39(1): 48-56. DOI: 10.14102/j.cnki.0254-5861.2011-2509 |
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| Authors: | ZENG Xiao-Lan SUN Xiao-Zi WANG He-Yu YU Yong-Sheng |
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| Affiliation: | College of Chemistry and Chemical Engineering,Xinyang Normal University, Xinyang 464000, China;College of Chemistry and Chemical Engineering,Xinyang Normal University, Xinyang 464000, China;College of Chemistry and Chemical Engineering,Xinyang Normal University, Xinyang 464000, China;College of Chemistry and Chemical Engineering,Xinyang Normal University, Xinyang 464000, China |
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| Abstract: | OH addition reactions of cationic, neutral and anionic forms of three sulfonamides(sulfamethoxazole, sulfadiazine and sulfapyridine) in aqueous solution were theoretically studied using density functional theory(DFT) method at the M06-2 X/6-311+G(3 df,2 p) level. Transition state theory was applied to estimate the secondary rate constants for these elementary reactions. The obtained results indicate that OH addition reactions of sulfonamides can take place spontaneously at standard conditions. The anionic form of three sulfonamides has the highest addition activity, while the corresponding cationic form is the most inactive addition reagent. The benzene ring of neutral forms of three sulfonamides is always a more favorable site for OH radical addition than the oxazole, pyrimidine or pyridine ring. C(3) or(and) C(5) atoms of benzene ring are the most favorable positions for OH addition occurring in benzene ring. Although the water solvent has no remarkable effect on OH addition reactions of neutral sulfonamides, it exerts a significant adverse influence on OH addition reactions of ionic sulfonamides. |
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