Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria
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 o...
| Main Authors: | , , , , , , , |
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| Format: | Journal Article |
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Elsevier BV
2014
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| Subjects: | |
| Online Access: | http://hdl.handle.net/20.500.11937/45418 |
| _version_ | 1848757278092558336 |
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| author | Hou, B. Yi, P. Wang, Z. Zhang, S. Zhao, J. Mancera, Ricardo Cheng, Y. Zuo, Z. |
| author_facet | Hou, B. Yi, P. Wang, Z. Zhang, S. Zhao, J. Mancera, Ricardo Cheng, Y. Zuo, Z. |
| author_sort | Hou, B. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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)σzz and NICS(max)πzz with respect to aromaticity are demonstrated, specifically between NICS(max)πzz and ELFπ (cc = 0.98) for π bonds. For σ bonds, the different electron delocalization of σ bonds out of the plane of the ring predicted well the discrepancies between NICS(max)σzz and ELFσ. The σ aromatic order of the classic heterobenzenes (C5H5N > C6H6 > C5H5P > C5H5As > C5H5Bi, C5H5Sb) was proved via the level of electronic delocalization. |
| first_indexed | 2025-11-14T09:25:33Z |
| format | Journal Article |
| id | curtin-20.500.11937-45418 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T09:25:33Z |
| publishDate | 2014 |
| publisher | Elsevier BV |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-454182019-02-19T04:25:45Z Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria Hou, B. Yi, P. Wang, Z. Zhang, S. Zhao, J. Mancera, Ricardo Cheng, Y. Zuo, Z. Global Aromaticity s Aromaticity p Aromaticity ELF Heterobenzenes NICS 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)σzz and NICS(max)πzz with respect to aromaticity are demonstrated, specifically between NICS(max)πzz and ELFπ (cc = 0.98) for π bonds. For σ bonds, the different electron delocalization of σ bonds out of the plane of the ring predicted well the discrepancies between NICS(max)σzz and ELFσ. The σ aromatic order of the classic heterobenzenes (C5H5N > C6H6 > C5H5P > C5H5As > C5H5Bi, C5H5Sb) was proved via the level of electronic delocalization. 2014 Journal Article http://hdl.handle.net/20.500.11937/45418 10.1016/j.comptc.2014.07.012 Elsevier BV fulltext |
| spellingShingle | Global Aromaticity s Aromaticity p Aromaticity ELF Heterobenzenes NICS Hou, B. Yi, P. Wang, Z. Zhang, S. Zhao, J. Mancera, Ricardo Cheng, Y. Zuo, Z. Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title | Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title_full | Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title_fullStr | Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title_full_unstemmed | Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title_short | Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| title_sort | assignment of aromaticity of the classic heterobenzenes by three aromatic criteria |
| topic | Global Aromaticity s Aromaticity p Aromaticity ELF Heterobenzenes NICS |
| url | http://hdl.handle.net/20.500.11937/45418 |