Anthralin: primary products of its redox reactions. J Org Chem 2006 Jul 07;71(14):5312-9
Date
07/01/2006Pubmed ID
16808521DOI
10.1021/jo060622oScopus ID
2-s2.0-33745685226 (requires institutional sign-in at Scopus site) 17 CitationsAbstract
One-electron reduction significantly enhances the ability of anthralin, 1, to act as a hydrogen atom donor. On annealing of an MTHF glass in which the radical anion of anthralin, 1*-, is generated radiolytically, this species decays mainly by loss of H* to give the anthralyl anion, 2- . On the other hand, radicals formed on radiolysis of matrices that are suitable for the generation of radical anions or cations are capable to abstract H* from anthralin to give the anthralyl radical, 2* . Both 2- and 2* are obtained simultaneously by mesolytic cleavage of the radical anion of the anthralin dimer. Contrary to general assumptions, the anthralyl radical is found to be much more reactive toward oxygen than the anion. All intermediates are characterized spectroscopically and by reference to quantum chemical calculations. Attempts to generate the radical cation of anthralin by X-irradiation of an Ar matrix containing anthralin led also to significant formation of its radical anion, i.e., anthralin acts apparently as an efficient electron trap in such experiments.
Author List
Czerwinska M, Sikora A, Szajerski P, Zielonka J, Adamus J, Marcinek A, Piech K, Bednarek P, Bally TAuthor
Jacek M. Zielonka PhD Assistant Professor in the Biophysics department at Medical College of WisconsinMESH terms used to index this publication - Major topics in bold
AnionsAnthralin
Cations
Electrons
Free Radicals
Molecular Structure
Oxidation-Reduction
Time Factors