The controversy over the nature of aromaticity and conjugation
Yu, ZH; Peng, XQ; Xuan, ZQ
AbstractIt is the most important general concept in organic chemistry that the pi electron delocalization is stabilizing. However, this concept, together with the ability of the pi electron delocalization to level out of differences in bond lengths between formal double and single bonds, the Huckel 4N + 2 theory, and the high stability of the pi system in benzene, was argued during the period of 1930's through 1990'9. The compounds, such as star - phenylene, linear and angular N - phenylene, tris( tri - carbonylironcyclobuta - dieno) benzene, 2, 7 - di - tert - butyl - 4, 5, 9, 10 - tetraphenylbenzo - 1,2,4,5 dicyclobutadiene were synthesized, and their crystallographic data were brought up as the experimental examples. These experimental results appear to support Shaik's viewpoint. On the other hand, the role of Mills - Nixon distortion in triannelated benzene was doubted by Siegel, and the stabilizing effect of the pi electron delocalization in benzene was reconfirmed by the Streitwieser. Meanwhile, various methods for energy partition, such as those of Morokuma, Shaik, Kollma, Jug, Streitwieser, Wolfe and Ichikawa, were reviewed and commented. Kollma's and related methods, in which the effects of the pi electron delocalization on the pi framework and on the Fock matrix have been neglected completely, were questioned. At last, our novel energy partition was introduced. More than 50 references were cited.
KeywordEnergy Partition Structure Theory Of Organic Chemistry The Nature Of Aromaticity And Resonance The Delocalization Of Pi-electron
Indexed BySCI
WOS IDWOS:000166806800006
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Cited Times:3[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorYu, ZH
AffiliationChinese Acad Sci, Inst Chem, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Yu, ZH,Peng, XQ,Xuan, ZQ. The controversy over the nature of aromaticity and conjugation[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2000,20(6):882-888.
APA Yu, ZH,Peng, XQ,&Xuan, ZQ.(2000).The controversy over the nature of aromaticity and conjugation.CHINESE JOURNAL OF ORGANIC CHEMISTRY,20(6),882-888.
MLA Yu, ZH,et al."The controversy over the nature of aromaticity and conjugation".CHINESE JOURNAL OF ORGANIC CHEMISTRY 20.6(2000):882-888.
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