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Stable N, N ′‐Di‐ tert ‐butyl‐meta‐phenylene‐bisnitroxides—Unexpected Ground‐State Singlets
Author(s) -
Dvolaitzky Maya,
Chiarelli Robert,
Rassat André
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199201801
Subject(s) - diradical , steric effects , ground state , chemistry , phenylene , singlet state , benzene , ring (chemistry) , photochemistry , radical , triplet state , oxygen atom , atom (system on chip) , crystallography , stereochemistry , molecule , organic chemistry , atomic physics , polymer , physics , excited state , computer science , embedded system
In contrast to m‐xylylene and related diradicals , bisnitroxide 1 has a singlet ground state according to ESR spectroscopic investigations. Diradical 1 can be isolated as two stable atropoisomers. In both, the free electron is possibly localized on the oxygen atom, because conjugation is prevented by the steric hindrance of the methyl groups. The parent compound with an unsubstituted benzene ring has a triplet ground state.