Electrochemical and spectroscopic characterization of N,N'-dialkylquinoxalinium redox systems
A. Schulz, and W. Kaim. Chemische Berichte, 124 (1):
129--139(1991)
Abstract
The outstanding position of the 1,4-isomer, quinoxaline, among the diazanaphthalenes is confirmed by comparing LUMO energies from HMO perturbation calcns. Diquaternary salts of quinoxaline, 2,3- and 6,7-dimethylquinoxaline and 2,3,6,7-tetramethylquinoxaline were isolated and characterized as compds. which are sensitive to redn. and hydrolysis. Cyclic voltammetry of the two-step redox systems of the Weitz type showed two reversible one-electron redns. with an extraordinarily stable radical-cation intermediate (log Kc \textgreater12). The redox potentials are less neg. than those of the 4,4'-bipyridinium systems but also less pos. than those of N,N'-dialkylphenazinium compds. The radical-cation intermediates, which include a TCNQ.bul.- salt, are characterized by ESR and by absorption spectroscopy in comparison to the resp. dications. on SciFinder(R)
%0 Journal Article
%1 Schulz.1991
%A Schulz, Andreas
%A Kaim, Wolfgang.
%D 1991
%J Chemische Berichte
%K ESR cation cyclic dialkylquinoxalinium dialkylquinoxalinium;spectra dialkylquinoxalinium;voltammetry electrochem property;redox radical;quinoxalinium spectral
%N 1
%P 129--139
%T Electrochemical and spectroscopic characterization of N,N'-dialkylquinoxalinium redox systems
%V 124
%X The outstanding position of the 1,4-isomer, quinoxaline, among the diazanaphthalenes is confirmed by comparing LUMO energies from HMO perturbation calcns. Diquaternary salts of quinoxaline, 2,3- and 6,7-dimethylquinoxaline and 2,3,6,7-tetramethylquinoxaline were isolated and characterized as compds. which are sensitive to redn. and hydrolysis. Cyclic voltammetry of the two-step redox systems of the Weitz type showed two reversible one-electron redns. with an extraordinarily stable radical-cation intermediate (log Kc \textgreater12). The redox potentials are less neg. than those of the 4,4'-bipyridinium systems but also less pos. than those of N,N'-dialkylphenazinium compds. The radical-cation intermediates, which include a TCNQ.bul.- salt, are characterized by ESR and by absorption spectroscopy in comparison to the resp. dications. on SciFinder(R)
@article{Schulz.1991,
abstract = {The outstanding position of the 1,4-isomer, quinoxaline, among the diazanaphthalenes is confirmed by comparing LUMO energies from HMO perturbation calcns. Diquaternary salts of quinoxaline, 2,3- and 6,7-dimethylquinoxaline and 2,3,6,7-tetramethylquinoxaline were isolated and characterized as compds. which are sensitive to redn. and hydrolysis. Cyclic voltammetry of the two-step redox systems of the Weitz type showed two reversible one-electron redns. with an extraordinarily stable radical-cation intermediate (log Kc {\textgreater}12). The redox potentials are less neg. than those of the 4,4'-bipyridinium systems but also less pos. than those of N,N'-dialkylphenazinium compds. The radical-cation intermediates, which include a TCNQ.bul.- salt, are characterized by ESR and by absorption spectroscopy in comparison to the resp. dications. [on SciFinder(R)]},
added-at = {2019-07-15T13:41:23.000+0200},
author = {Schulz, Andreas and Kaim, Wolfgang.},
biburl = {https://puma.ub.uni-stuttgart.de/bibtex/25e886cb0a874a8dd5e3b896cf05536ee/b_schwederski},
interhash = {b93673563b609880f4569ba56a101a2d},
intrahash = {5e886cb0a874a8dd5e3b896cf05536ee},
issn = {0009-2940},
journal = {Chemische Berichte},
keywords = {ESR cation cyclic dialkylquinoxalinium dialkylquinoxalinium;spectra dialkylquinoxalinium;voltammetry electrochem property;redox radical;quinoxalinium spectral},
number = 1,
pages = {129--139},
timestamp = {2019-07-15T11:42:10.000+0200},
title = {Electrochemical and spectroscopic characterization of N,N'-dialkylquinoxalinium redox systems},
volume = 124,
year = 1991
}