Electronic spectra of the electrogenerated 1,4-benzoquinone π-dianion and the strongly hydrogen-bonded charge-transfer complex with methanol

被引:38
作者
Okumura, N [1 ]
Uno, B [1 ]
机构
[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan
关键词
D O I
10.1246/bcsj.72.1213
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electronic spectra of the active pi-electronic dianion of 1,4-benzoquinone and its hydrogen-bonded complex with CH3OH, generated at sequential electroreduction steps, have been discussed from the points of view of the observation techniques and n-sigma charge-transfer interaction of the dianion with a weak hydrogen donor. An improved method involving rapid circulation of the electrolyzed solution via a photodiode array detector to avoid comproportionation and side reactions was used for successful measurements of the clear spectra resulting from the dianion generation. CNDO/S-CI calculations well reproduced the longest-wavelength band observed for the dianion, assigning to the benzenoid B-1(3u)<--(1)A(g), band under D-2h symmetry. The hydrogen-bonding interaction of the 1,4-benzoquinone dianion with CH3OH allows the B-1(3u)<--(1)A(g) band to be blue-shifted. This behavior has been well explained in terms of the strong n-sigma type charge-transfer interaction of the dianion with CH3OH. These results have been extensively discussed with regard to coupled electron and proton transfer reactions in the quinone-hydroquinone redox system.
引用
收藏
页码:1213 / 1217
页数:5
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