Conjugation in the Biphenyl System
Conjugation in the Biphenyl System
复制标题
联苯体系中的共轭
DOI：
10.1021/ja01651a042
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发表时间：
1954
期刊：
影响因子：
--
通讯作者：
R. H. Eastman
中科院分区：
文献类型：
--
作者：
V. P. Kreiter;W. Bonner;R. H. Eastman
用分光光度法测定了3-羟基联苯、4-羟基联苯、3‘-硝基-4-羟基联苯、4’-硝基-4-羟基联苯、2-羟基荧和2-羟基-7-硝基-2-呋喃在S硼酸-硼酸缓冲溶液中的离解常数。这些数据被解释为通过贡献两个苯环之间的共轭结构对这些化合物的共轭碱基的基态电子结构的贡献而缺乏显著贡献。最近关于3‘-或4’-位X基团对取代联苯4-位取代基Y的反应性的研究提出了一些问题，即联苯体系是否能够通过涉及苯醌的共振杂交来传递取代基效应
The dissociation constants of 3-hydroxybiphenyl, 4-hydroxybiphenyl, 3'-nitro-4-hydroxybiphenyl, 4'-nitro-4-hydroxy-biphenyl, 2-hydroxyfluorene and 2-hydroxy-7-nitrofluorene havebeen measured by a spectrophotometric method in aqueou s borate-boric acid buffers. The data are interpreted as indicating a lack of significantcontribution by contributing struc-tures involving conjugation between the two benzene rings to the electronic structures of the ground states of the conjugate bases of these compounds. An explanation of this conclusion is given.Recent studies of the effect of a group X in the 3'-or 4'-position on the reactivity of a substituent Y in the 4-position of a substituted biphenyl have raised some question as to the ability of the biphenyl system to transmit substituent effects by resonance hybridization involving the quinonoid