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ESR‐Spectroscopic Investigation of Radical Cations, Radical Anions, and Radical Trianions of Didehydro[n]annulenes
Author(s) -
Huber Walter
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680508
Subject(s) - chemistry , annulene , radical ion , hyperfine structure , radical , alkali metal , hyperfine coupling , paramagnetism , medicinal chemistry , photochemistry , ion , crystallography , computational chemistry , organic chemistry , atomic physics , physics , quantum mechanics
The didehydro[n]annulenes 1 (n = 14), 2 (n = 18), and 3 (n = 22) are oxidized to radical cations. Reduction of the title compounds leads to radical anions and, in the case of 2 and 3 , to radical trianions. The hyperfine data of the paramagnetic derivatives are rationalized in terms of the occupation of n‐membered (n = 14, 18, 22) π‐perimeter MO's (HOMO, LUMO, NLUMO). The contact‐ion pairs of the radical anions show unexpectedly large alkali‐metal coupling constants.