Correlation of electronic transitions and redox potentials measured for pyrocatechol, resorcinol, hydroquinone, pyrogallol, and gallic acid with results of semi-empirical molecular orbital computations A useful interpretation tool

作者: Melvin Keith Carter

DOI: 10.1016/J.MOLSTRUC.2006.07.020

关键词:

摘要: Abstract Cyclic voltammogram (CV) electrochemical measurements for pyrocatechol, resorcinol, hydroquinone, pyrogallol, and gallic acid in strong alkaline solution produced observable oxidation–reduction potentials each hydroxy group present except resorcinol. UV absorption spectra were also observed the diluted solutions. Semi-empirical molecular orbital computations conducted these molecules of C 2 v point symmetry to determine character energies aid interpretation experimental results. CV oxidation removed a π-electron by radiationless π–π* transition followed an electron shift from negative oxygen positive aromatic π-system indicated σ–π* transition. Simple semi-empirical correlated with measured excited electronic states during transfer.

参考文章(17)
Walter R. Duncan, Oleg V. Prezhdo, Electronic structure and spectra of catechol and alizarin in the gas phase and attached to titanium. Journal of Physical Chemistry B. ,vol. 109, pp. 365- 373 ,(2005) , 10.1021/JP046342Z
Chiara Cappelli, Benedetta Mennucci, Susanna Monti, Environmental effects on the spectroscopic properties of gallic acid: a combined classical and quantum mechanical study. Journal of Physical Chemistry A. ,vol. 109, pp. 1933- 1943 ,(2005) , 10.1021/JP044781S
Paul B. Comita, John I. Brauman, Photodissociation spectroscopy of the negative ion dimer of toluquinone Journal of the American Chemical Society. ,vol. 109, pp. 7591- 7597 ,(1987) , 10.1021/JA00259A001
Paul. Kebarle, Swapan. Chowdhury, Electron affinities and electron-transfer reactions Chemical Reviews. ,vol. 87, pp. 513- 534 ,(1987) , 10.1021/CR00079A003
Daniel E. Wheeler, James K. McCusker, Electron Exchange and the Photophysics of Metal-Quinone Complexes. 1. Synthesis and Spectroscopy of Chromium-Quinone Dyads Inorganic Chemistry. ,vol. 37, pp. 2296- 2307 ,(1998) , 10.1021/IC971306I
Ronald S. Giordano, Robert D. Bereman, Daniel J. Kosman, Murray J. Ettinger, Stereoelectronic properties of metalloenzymes. II. Effects of ligand coordination on the electron spin resonance spectrum of galactose oxidase as a probe of structure and function. Journal of the American Chemical Society. ,vol. 96, pp. 1023- 1026 ,(1974) , 10.1021/JA00811A013
K.K. Kalninsh, R. Gadonas, V. Krasauskas, A. Pelakauskas, A. Pugzhlys, Steady state and transient absorption spectra of quinhydrones Journal of Photochemistry and Photobiology A-chemistry. ,vol. 77, pp. 9- 16 ,(1994) , 10.1016/1010-6030(94)80002-2
Andreas Dreuw, Martin Head-Gordon, Single-reference ab initio methods for the calculation of excited states of large molecules. Chemical Reviews. ,vol. 105, pp. 4009- 4037 ,(2005) , 10.1021/CR0505627
A. A. Kasanein, M. S. Masoud, M. M. Habeeb, Spectral Studies On Some Phenol derivatives Spectroscopy Letters. ,vol. 21, pp. 481- 492 ,(1988) , 10.1080/00387018808062728