Computational Investigation of the Substituent Effect on the Intramolecular Proton Transfer Reaction of 3-Hydroxytropolone

作     者：GüL Vedat IsIN Dilara ozbakir 

作者机构：Chemistry DepartmentFaculty of ScienceCumhuriyet University 58140 SivasTurkey 

出 版 物：《Chinese Journal of Structural Chemistry》 (结构化学（英文）)

年 卷 期：2014年第33卷第12期

页      面：1757-1767页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 070304[理学-物理化学(含∶化学物理)] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

主　　题：tropolone derivative 3-hydroxytropolone the proton transfer reaction density functional theory 

摘      要：The effects of substituent type and position on the proton transfer reaction of 3-hydroxytropolone(3-OHTRN) have been investigated theoretically by using density functional theory at the level of B3LYP/ 6-31+G** method. The influence of solvent on the proton transfer reactions of substituted 3-OHTRN has been examined using the self-consistent isodensity polarized continuum model(SCI-PCM) in water. As a result, while the proton transfer reaction is kinetically the easiest by substitution on position 3 of-NH2 group in the gas phase, it is kinetically the easiest by substitution on position 5 of the same group in water. In addition, these reactions are either kinetically or thermodynamically easier in the gas phase than that in water, except the reaction of structure with-NH2 group at position 6.