Antiaromaticity in open-shell cyclopropenyl to cycloheptatrienyl cations, anions, free radicals, and radical ions

被引:131
作者
Allen, AD [1 ]
Tidwell, TT [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/cr990316t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cationic, anionic, and free radical conjugated cyclic hydrocarbons were studied. The ESR spectrum of the cycloheptatrienyl radical 9 was also discussed both in solutions and in matrixes and it was observed that the radical shows an eight-line spectrum that was assumed to arise from a planar, symmetrical structure. The results suggest that antiaromaticity is a highly useful concept and demonstrates the powerful predictive ability of the simple Hückel-derived rule.
引用
收藏
页码:1333 / 1348
页数:16
相关论文
共 239 条
[51]   STRUCTURE AND DYNAMICS OF THE TRIMETHYLCYCLOPROPENYL RADICAL AS DETERMINED BY ELECTRON AND NUCLEAR MAGNETIC-RESONANCE [J].
CLOSS, GL ;
EVANOCHKO, WT ;
NORRIS, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :350-352
[52]   CHARACTERIZATION OF MATRIX-ISOLATED CYCLOPROPEN-3-YL BY ELECTRON-PARAMAGNETIC-RES SPECTROSCOPY [J].
CLOSS, GL ;
REDWINE, OD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :506-507
[53]  
COMBETFARNOUX F, 1959, CR HEBD ACAD SCI, V248, P688
[54]   REACTIVITY IN NUCLEOPHILIC SUBSTITUTION .3. ACETOLYSIS OF 9-FLUORENYL TOULENE-P-SULPHONATE [J].
COWELL, GW ;
LEDWITH, A .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1967, (07) :695-&
[55]   REACTIVITY IN NUCLEOPHILIC SUBSTITUTION .2. KINETICS AND MECHANISM OF HYDROLYSIS OF 9-FLUORENYL TOLUENE-P-SULPHONATE IN AQUEOUS ACETONE [J].
COWELL, GW ;
GEORGE, TD ;
LEDWITH, A ;
MORRIS, DG .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (12) :1169-&
[56]  
COZENS F, 1992, ANGEW CHEM INT EDIT, V31, P743, DOI 10.1002/anie.199207431
[57]  
COZENS NP, 1992, J CHEM SOC P2, P2083
[58]   Reaction of benzylic α-hydroxythioamides with thionyl chloride [J].
Creary, X ;
Tricker, J .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :4907-4911
[59]  
Creary X, 2000, J PHYS ORG CHEM, V13, P337, DOI 10.1002/1099-1395(200006)13:6<337::AID-POC249>3.3.CO
[60]  
2-K