Theoretical Studies on the Iodine-catalyzed Nucleophilic Addition of Acetone with Five-membered Heterocycles
Theoretical Studies on the Iodine-catalyzed Nucleophilic Addition of Acetone with Five-membered Heterocycles作者机构：College of Biology and Environment Engineering Zhejiang Shuren University Hangzhou 310015 P. R. China
出 版 物：《Chemical Research in Chinese Universities》 (高等学校化学研究（英文版）)
年 卷 期：2008年第24卷第4期
页 面：520-524页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 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] 070301[理学-无机化学]
基 金：the Natural Science Foundation of Zhejiang Province China(No.Y406374)
主 题：Halogen bond, Catalytic effect Nucleophilic addition Density functional theory
摘 要：The iodine-catalyzed nucleophilic addition reactions of pyrrole, furan, or thiophene with acetone were studied in gas and solvent by the density functional theory at the level of Lanl2DZ^＊. It was seen that the halogen bond between iodine and carbonyl oxygen appeared to have an important catalytic effect on such reactions, and the first iodine molecule maximally diminished the barrier height by 41 kJ/mol, while the second iodine molecule could not improve such reactions largely. It was concluded that the C2-addition was generally more favorable than the C3-addition for the three heterocycles; however, iodine considerably more effectively catalyzed the C3-addition than the C2-addition for pyrrole. It was also revealed by PCM calculation that the iodine-catalyzed nucleophilic additions occurred more easily in solvent than in gas, which explained the experiment performed by Bandgar et al..
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