GAS-PHASE SUBSTITUENT EFFECT ON BASICITY OF PHENYLACETYLENE - INTRINSIC RESONANCE DEMAND OF PHENYLVINYL CATION

被引:16
作者
MISHIMA, M
ARIGA, T
FUJIO, M
TSUNO, Y
KOBAYASHI, S
TANIGUCHI, H
机构
[1] KYUSHU UNIV, FAC SCI, DEPT CHEM, HIGASHI KU, FUKUOKA 812, JAPAN
[2] KYUSHU UNIV, FAC ENGN, DEPT APPL CHEM, HIGASHI KU, FUKUOKA 812, JAPAN
关键词
D O I
10.1246/cl.1992.1085
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The substituent effect on gas-phase basicity of phenylacetylene has been analyzed in terms of the LArSR Eq., providing an r of 1.21 and a rho of -14.1. The magnitude of the r is reconciled with the "resonance demand - carbocation stability relation" derived from sp2-hybridized benzylic carbocations.
引用
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页码:1085 / 1088
页数:4
相关论文
共 28 条
[1]   SUBSTITUENT EFFECTS ON THE ACID HYDRATION OF ACETYLENES [J].
ALLEN, AD ;
CHIANG, Y ;
KRESGE, AJ ;
TIDWELL, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (05) :775-779
[2]  
Aue DH, 1979, GAS PHASE ION CHEM, V2, P2
[3]   SUBSTITUENT EFFECTS IN ACID-CATALYSED HYDRATION OF PHENYLACETYLENES [J].
BOTT, RW ;
EABORN, C ;
WALTON, DRM .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :384-&
[4]   INTERMEDIACY OF CARBONIUM IONS IN ADDITION OF WATER OR ETHANOL TO ARYLALKENES [J].
DENO, NC ;
KISH, FA ;
PETERSON, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (10) :2157-&
[5]   SUBSTITUENT EFFECTS IN THE SOLVOLYSIS OF BENZYL TOSYLATES [J].
FUJIO, M ;
GOTO, M ;
SUSUKI, T ;
MISHIMA, M ;
TSUNO, Y .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (07) :449-455
[6]   SOLVOLYSIS OF ALPHA-BROMO PARA AMINOSTYRENE - MESOMERIC VINYL CATIONNS .4. [J].
GROB, CA ;
PFAENDLE.HR .
HELVETICA CHIMICA ACTA, 1971, 54 (07) :2060-&
[7]   GAS-PHASE BASICITY OF RING-SUBSTITUTED PHENYLACETYLENES [J].
MARCUZZI, F ;
MODENA, G ;
PARADISI, C ;
GIANCASPRO, C ;
SPERANZA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4973-4975
[8]  
Mishima M., 1985, Memoirs of the Faculty of Science, Kyushu University, Series C, V15, P111
[9]   GAS-PHASE SUBSTITUENT EFFECTS IN A HIGHLY ELECTRON DEFICIENT SYSTEM - INTRINSIC RESONANCE DEMAND OF 1-ARYL-1-(TRIFLUOROMETHYL)ETHYL CATION [J].
MISHIMA, M ;
INOUE, H ;
FUJIO, M ;
TSUNO, Y .
TETRAHEDRON LETTERS, 1989, 30 (16) :2101-2104
[10]  
MISHIMA M, 1990, TETRAHEDRON LETT, V31, P685