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
Source PublicationCOMPUTATIONAL AND THEORETICAL CHEMISTRY
ISSN2210-271X
Volume1046Pages:20-24
Contribution Rank第一
AbstractAromaticity 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.
KeywordNics Elf Heterobenzenes Global Aromaticity Pi Aromaticity Sigma Aromaticity
Subject AreaChemistry
DOI10.1016/j.comptc.2014.07.012
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Physical
WOS IDWOS:000342542600004
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/18398
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorYi,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
Affiliation1.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
Recommended Citation
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.
Files in This Item: Download All
File Name/Size DocType Version Access License
Hou-2014-Assignment (847KB) 开放获取CC BY-NC-SAView Download
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Hou, Bo]'s Articles
[Yi, Pinggui]'s Articles
[Wang, Zhaoxu]'s Articles
Baidu academic
Similar articles in Baidu academic
[Hou, Bo]'s Articles
[Yi, Pinggui]'s Articles
[Wang, Zhaoxu]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Hou, Bo]'s Articles
[Yi, Pinggui]'s Articles
[Wang, Zhaoxu]'s Articles
Terms of Use
No data!
Social Bookmark/Share
File name: Hou-2014-Assignment of aromat.pdf
Format: Adobe PDF
This file does not support browsing at this time
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.