An Electron Spin Resonance Study of Several 1,4-Dihydro-s-tetrazine Cation Radicals
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Authors
Tolles, W.M.
McBride, William R.
Thun, Wayne E.
Subjects
Advisors
Date of Issue
1969-05-01
Date
May 1, 1969
Publisher
ACS Publications
Language
Abstract
The one-electron oxidation of 1,4-dihydro-s-tetrazines using concentrated iodine solutions of tetrahydrofuran as oxidant gives rise to a new class of relatively stable cation radicals. In the presence of water and air these radical cations in solution are stable for periods of hours to several days. The esr spectra for radical cations of 1,4-dimethyl-, 1,4-diphenyl-, 1,4-dimethyl-3,6-diphenyl-1, ,3,4,6-tetraphenyl-, and 1,4-bis(p-bromopheny1)-3,6- diphenyl-l,4-dihydro-s-tetrazineasr e interpreted and compared with molecular orbital calculations using the CND0/2 method to obtain the molecular orbital parameters. Assignment of the esr nitrogen coupling constants indicates nearly the same value for the five members of the series studied. The formation of the previously unreported 1, 4-dimethyl-1,4-dihydro-s-tetrazine, first identified as its radical cation in several different reactions, is discussed.
Type
Article
Description
The article of record as published may be found at http://dx.doi.org/10.1021/ja01038a007
Series/Report No
Department
Chemistry
Organization
Identifiers
NPS Report Number
Sponsors
Director of Naval Laboratories
Office of Naval Research
Office of Naval Research
Funding
Format
4 p.
Citation
Electron spin resonance study of several 1,4-dihydro-s-tetrazine cation radicals
William M. Tolles, William R. McBride, Wayne E. Thun
J. Am. Chem. Soc., 1969, 91 (10), pp 2443–2446
Distribution Statement
Rights
This publication is a work of the U.S. Government as defined in Title 17, United States Code, Section 101. Copyright protection is not available for this work in the United States.