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
2014-10-15
发表期刊COMPUTATIONAL AND THEORETICAL CHEMISTRY
ISSN2210-271X
卷号1046页码:20-24
产权排序第一
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
资助信息National Natural Science Foundation of China [21172066, 20772027]; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences [P2013-ZZ05]
学科领域Chemistry
DOI10.1016/j.comptc.2014.07.012
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Physical
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
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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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