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Electrochemical and electron spin resonance investigations of some 1,2,3‐oxa‐ and ‐thiadiazoles
Author(s) -
Stuhlmann F.,
Domschke G.,
Bartl A.,
Omelka L.
Publication year - 1998
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199801)36:1<8::aid-omr190>3.0.co;2-7
Subject(s) - chemistry , mesoionic , acetonitrile , electrochemistry , electron paramagnetic resonance , radical , thiadiazoles , cationic polymerization , ion , resonance (particle physics) , spectroscopy , cyclic voltammetry , photochemistry , inorganic chemistry , medicinal chemistry , nuclear magnetic resonance , organic chemistry , electrode , physics , particle physics , quantum mechanics
Voltammetric studies on mesoionic 1,2,3‐oxa‐ and ‐thiadiazoles confirmed that the former may be reduced irreversibly at potentials between ‐1.48 and ‐2.12 V vs . Fc/Fc + in acetonitrile at a scan rate of 200 mV s ‐1 , whereas the latter are reduced reversibly under the same conditions. The corresponding anion radicals were examined by ESR spectroscopy. Cationic alkylation products showed different electrochemical behaviour depending on the character of the heterocyclic ring. 1,2,3‐Thiadiazolium ions were reduced reversibly. All coupling constants of the resulting neutral radicals were fully assigned. 1,2,3‐Oxadiazolium ions were all reduced irreversibly. © 1997 John Wiley & Sons, Ltd.