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UV-laser photochemistry: diffusion-controlled trapping of cyclic 1,3-diradicals by molecular oxygen. Conformational effects on triplet lifetimes

Journal Article · · J. Am. Chem. Soc.; (United States)
DOI:https://doi.org/10.1021/ja00258a074· OSTI ID:5674265
To explore the effects of methyl substitution at radical sites and ring size, 1,3-diradicals were generated from respective azoalkanes and oxygen trapping determined quantitatively. Molecular mechanics calculations suggest that in the lowest energy conformations the interorbital angles are ca. 0/sup 0/, 45/sup 0/, and 60/sup 0/ for the 1,3-diradicals, respectively. Thus, for the planar cyclopenta-1,3-diyl (planarity confirmed be ESR) intersystem crossing spin-orbital coupling should be most difficult, and hence it should have a relatively long triplet lifetime. In contrast, the rigid puckered bicyclo(2.2.1)hepta-2,7-diyl should be the most short-lived species of the three. The flexible twist-boat conformation of the cyclohexa-1,3-diyl possesses intermediate lifetime. Other than such conformational effects, it is difficult to rationalize the lifetimes of these rather similar 1,3-diradicals.
Research Organization:
Univ. of Wuerzburg/Am Hubland, Germany, F.R.
OSTI ID:
5674265
Journal Information:
J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 109:24; ISSN JACSA
Country of Publication:
United States
Language:
English