STERIC EFFECTS - INVERSION OF 4,5-DISUBSTITUTED 9,10-DIHYDROPHENANTHRENES

STERIC EFFECTS - INVERSION OF 4,5-DISUBSTITUTED 9,10-DIHYDROPHENANTHRENES
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DOI:
10.1071/ch9870035
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发表时间:
1987-01-01
影响因子:
1.1
通讯作者:
STERNHELL, S
STERNHELL, S
中科院分区:
化学4区
文献类型:
--
作者:
COSMO, R;STERNHELL, S

文献摘要

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合成了6个4,5-二-X-9,10-二氢菲(X=H,F,OCH3,Cl,CH3,CF3),并用核磁共振研究了它们的转化率。在标准温度下(∆G‡;340)的反转势垒范围从-lt;25到>120kJ·m ol-L,并与C4和C5上相互作用取代基的范德华半径以及先前提出的‘表观重叠’参数有很好的相关性。
Six 4,5-di-X-9,l0-dihydrophenanthrenes (X = H, F, OCH3, Cl, CH3, CF3) were synthesized and their inversion rates were investigated by n.m.r., spectroscopy. The barriers to inversion at a standard temperature (∆G‡;340) ranged from <25 to >120 kJ mol-l and showed good correlation with the van der Waals radii of the interacting substituents at C4 and C5 and with the previously proposed 'apparent overlap' parameter.