Computational Study on OH Addition Reactions of Three Sulfonamides in Aqueous Solution  

作　　者：ZENG Xiao-Lan SUN Xiao-Zi WANG He-Yu YU Yong-Sheng 曾小兰;孙小孜;王贺宇;于永生(College of Chemistry and Chemical Engineering,Xinyang Normal University,Xinyang 464000,China)

机构地区：[1]College of Chemistry and Chemical Engineering,Xinyang Normal University,Xinyang 464000,China

出　　处：《Chinese Journal of Structural Chemistry》2020年第1期48-56,2,共10页结构化学（英文）

基　　金：This project was supported by the National Natural Science Foundation of China(No.21876143);Science and Technology Program of Henan Province(No.172102210088);Nanhu Scholars Program for Young Scholars of XYNU。

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.

关 键 词：addition reaction SULFONAMIDE OH RADICALS REACTIVITY order position SELECTIVITY 

分 类 号：O621.25[理学—有机化学] X703[理学—化学]