Journal
STRUCTURAL CHEMISTRY
Volume 20, Issue 3, Pages 399-407Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s11224-009-9424-1
Keywords
Singlet oxygen; Naphthalene endoperoxide; Jump rope dynamics; Paddlane
Funding
- NIH [S06 GM076168-01]
- PSC-CUNY Grants Program
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Theoretical calculations have been used to examine singlet oxygen release from a naphthalene endoperoxide which bears a flexible (CH2)(22) polymethylene lid. Monte Carlo and ONIOM calculations that incorporated semi-empirical and density functional theory predicted the conformational influence of the polymethylene chain in the cycloreversion of dioxapaddlane, 1,4-diicosa naphthalene-1,4-endoperoxide, to O-1(2) and 1,4-diicosa naphthalene. This study attempts to build a connection between O-1(2) generation and jump rope dynamics of the dioxapaddlane. The polymethylene chain appears to function as a gatekeeper for the oxygen. Instead of coming full circle, a semi-circle rotation of the polymethylene bridge protected the peroxide group, limiting the dissociation of O-1(2) from the naphthalene site.
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