| Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria | |
Hou, Bo1,2; Yi, Pinggui2; Wang, Zhaoxu2; Zhang, Shuqun1; Zhao, Jinhua1 ; Mancera, Ricardo L.3; Cheng, Yongxian1; Zuo, Zhili1; Yi,PG (reprint author),Hunan Univ Sci & Technol,Minist Educ,Key Lab Theoret Chem & Mol Simulat,Xiangtan 411201,Peoples R China.; zuozhili@mail.kib.ac.cn
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| 2014-10-15 | |
| 发表期刊 | COMPUTATIONAL AND THEORETICAL CHEMISTRY
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| ISSN | 2210-271X |
| 卷号 | 1046页码:20-24 |
| 摘要 | Aromaticity is a key concept in physical organic chemistry. The aromatic order of the classic heterobenzenes was reported in experiment early. However, the unambiguous criteria used to validate the aromaticity of that were controversial or inadequate in theory. In this work, the global aromaticity of the compounds has been studied using the ELF, NICS and ISE. NICS(max)(zz) was calculated based on the maximum NICS contribution to the out-of-plane zz tensor component. Two types of bonds are observed. The correlations between NICS(max)(sigma zz) and NICS(max)(pi zz) with respect to aromaticity are demonstrated, specifically between NICS(max)(pi zz), and ELF pi (cc = 0.98) for pi bonds. For a bonds, the different electron delocalization of sigma bonds out of the plane of the ring predicted well the discrepancies between NICS(max)(sigma zz) and ELF sigma. The sigma aromatic order of the classic heterobenzenes (C6H5N > C6H6 > C5H5P > C5H5As > C5H5Bi, C5H5Sb) was proved via the level of electronic delocalization. (C) 2014 Elsevier B.V. All rights reserved. |
| 关键词 | Nics Elf Heterobenzenes Global Aromaticity Pi Aromaticity Sigma Aromaticity |
| 学科领域 | Chemistry |
| DOI | 10.1016/j.comptc.2014.07.012 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000342542600004 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/18398 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 通讯作者 | Yi,PG (reprint author),Hunan Univ Sci & Technol,Minist Educ,Key Lab Theoret Chem & Mol Simulat,Xiangtan 411201,Peoples R China.; zuozhili@mail.kib.ac.cn |
| 作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Hunan Univ Sci & Technol, Minist Educ, Key Lab Theoret Chem & Mol Simulat, Xiangtan 411201, Peoples R China 3.Curtin Univ, CHIRI Biosci, Sch Biomed Sci, Perth, WA 6845, Australia |
| 推荐引用方式 GB/T 7714 | Hou, Bo,Yi, Pinggui,Wang, Zhaoxu,et al. Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria[J]. COMPUTATIONAL AND THEORETICAL CHEMISTRY,2014,1046:20-24. |
| APA | Hou, Bo.,Yi, Pinggui.,Wang, Zhaoxu.,Zhang, Shuqun.,Zhao, Jinhua.,...&zuozhili@mail.kib.ac.cn.(2014).Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria.COMPUTATIONAL AND THEORETICAL CHEMISTRY,1046,20-24. |
| MLA | Hou, Bo,et al."Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria".COMPUTATIONAL AND THEORETICAL CHEMISTRY 1046(2014):20-24. |
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