Consideration on the effect of ortho-substituents of phenols by semiempirical molecular orbital method MOPAC
Consideration on the effect of ortho-substituents of phenols by semiempirical molecular orbital method MOPAC
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DOI：
10.1016/s0141-3910(99)00157-3
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发表时间：
2000-01-01
影响因子：
5.9
通讯作者：
Tobita, E
中科院分区：
文献类型：
--
作者：
Ohkatsu, Y;Ishikawa, S;Tobita, E
用MOPAC计算解释了作者提出的新的苯酚邻位取代效应：邻位取代基上的α-氢被用来从苯氧基再生苯酚。苯氧基分子内氢转移生成的苄基与苯氧基一样稳定，甚至比苯氧基更稳定。再生的苯酚也比由一个苯氧基和另一个过氧基反应形成的奎宁型化合物更稳定。因此，上述新的邻位取代基效应也可以用这项工作很好地解释。(C)2000爱思唯尔科学有限公司。保留所有权利。
A MOPAC calculation is performed to explain the new ortho-substitutent effect of phenols proposed by the authors; an alpha-hydrogen of an ortho-substituent being used to regenerate a phenol from the phenoxy radical. The benzyl radical derived from the intramolecular hydrogen transfer of a phenoxy radical is found to be as stable as, or more stable than, the phenoxy radical. The regenerated phenol also is strikingly more stable than a quinoid type compound formed by the reaction of a phenoxy radical with another peroxy radical. Thus, the new ortho-substituent effect mentioned above can also be well explained by this work. (C) 2000 Elsevier Science Ltd. All rights reserved.