| Theoretical Study of the Iodine-catalyzed Nucleophilic Addition by Halogen Bond |
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| 作者姓名： | WANG Yan-Hua SHEN Tu Chao TONG Jian-Ying |
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| 作者单位： | College of Biology and Environment Engineering of Zhejiang Shuren University，College of Biology and Environment Engineering of Zhejiang Shuren University，College of Biology and Environment Engineering of Zhejiang Shuren University Hangzhou 310015，China，Hangzhou 310015，China，Hangzhou 310015，China |
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| 摘 要： | The iodine-catalyzed nucleophilic addition of pyrrole to acetone has been studied by density functional theory at the level of Lanl2DZ. It has been shown that the first iodine molecule appears to have a remarkable catalytic effect on this reaction by halogen bond between carbonyl oxygen and iodine molecule,but the second one does not improve the reaction largely. In general,the nucleophilic addition at the C(2) site of pyrrole is more favorable than that at the C(3) site; however,this trend is not prominent or even changed in acetronitrile solvent for the indole system,which is consistent with the experimental result by Bandgar.
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| 关 键 词： | 卤素 催化作用 密度函数理论 碘元素 |
| 收稿时间： | 2006-12-26 |
| 修稿时间： | 2007-02-07 |
Theoretical Study of the Iodine-catalyzed Nucleophilic Addition by Halogen Bond |
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| WANG Yan-Hua SHEN Tu Chao TONG Jian-Ying.Theoretical Study of the Iodine-catalyzed Nucleophilic Addition by Halogen Bond[J].Chinese Journal of Structural Chemistry,2007,26(10):1189-1195. |
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| Authors: | WANG Yan-Hua SHEN Tu Chao TONG Jian-Ying |
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| Abstract: | The iodine-catalyzed nucleophilic addition of pyrrole to acetone has been studied by density functional theory at the level of Lanl2DZ*. It has been shown that the first iodine molecule appears to have a remarkable catalytic effect on this reaction by halogen bond between carbonyl oxygen and iodine molecule, but the second one does not improve the reaction largely. In general, the nucleophilic addition at the C(2) site of pyrrole is more favorable than that at the C(3)site;however, this trend is not prominent or even changed in acetronitrile solvent for the indole system, which is consistent with the experimental result by Bandgar. |
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| Keywords: | halogen bond catalytic effect nucleophilic addition density functional theory Bond Halogen Nucleophilic Addition Study consistent experimental result trend solvent indole system however site general improve catalytic effect reaction halogen bond carbonyl |
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