ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The radical anion and the radical cation of azuleno[1,2,3-cd]phenalene (III) have been investigated by ESR. spectroscopy, along with the radical anion of 2-phenylazulene (IV). Also studied has been the neutral radical obtained by one-electron reduction of cyclohepta[cd]phenalenium-cation (VI⊕). Assignment of the proton coupling constants for the radical ions III. ·⊖, III ·⊕ and IV·⊕, and the radical VI · is supported by comparison with the ESR. spectra of specifically deuteriated derivatives III-d5 ·⊖, III-d5 ·⊕, IV-d2 ·⊖ and VI-d1′. The experimental results are in full accord with qualitative topological arguments and predictions of HMO models. Whereas the radical anion III ·⊖ exhibits α-spin distribution similar to that of IV ·⊖the corresponding radical cation III ·⊕ and the neutral radical VI · are related in this respect to phenalenyl (V·). It is noteworthy that oxidation of III by conc. H2SO4 yields a paramagnetic species (IIIa ·⊕) which has a similar - but not an identical - structure as the radical cation III ·⊕ produced from III with AlCl3 in CH3NO2.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19750580827
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