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Properties of Hafner's new heptalene and pentalene derivatives

 

作者: M. Asgar Ali,   C.A. Coulson,  

 

期刊: Molecular Physics  (Taylor Available online 1961)
卷期: Volume 4, issue 1  

页码: 65-79

 

ISSN:0026-8976

 

年代: 1961

 

DOI:10.1080/00268976100100091

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

A critical study has been made of Hafner's new heptalene and pentalene derivatives I and II. Conventional valence-bond, molecular-orbital and free-electron approximations have been used. All agree that I should be genuinely aromatic, and II should not be. The valence-bond method suggests that II should be pseudo-aromatic, the other methods suggest that it should possess cyclo-olefinic character. All methods confirm the very long wavelength absorption of I, but the agreement in the case of II is less satisfactory. Charge distributions, bond orders and lengths are calculated by the molecular-orbital method, and compared with heptalene, pentalene, azulene and acenaphthylene. The relevance of the aromatic sextet rule is pointed out in discussing charge distribution in these odd-numbered ring compounds. Localization energies are also calculated, and are used to predict the positions of greatest reactivity for electrophilic, nucleophilic and radical reactions.

 

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