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Theoretical studies of a singlet oxygen-releasing dioxapaddlane (1,4-diicosa naphthalene-1,4-endoperoxide)

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Abstract

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 1O2 and 1,4-diicosa naphthalene. This study attempts to build a connection between 1O2 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 1O2 from the naphthalene site.

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Acknowledgments

We thank the NIH (S06 GM076168-01) and the PSC-CUNY Grants Program for support. Computational support was provided by the CUNY Graduate Center computational facility. We thank Prof. Mark Kobrak for stimulating discussions.

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  1. Department of Chemistry and Graduate Center, Brooklyn College, The City University of New York (CUNY), Brooklyn, NY, 11210, USA

    Alvaro Castillo & Alexander Greer

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  1. Alvaro Castillo
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Correspondence to Alexander Greer.

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Dedicated to István Hargittai for his first twenty years at Structural Chemistry.

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Castillo, A., Greer, A. Theoretical studies of a singlet oxygen-releasing dioxapaddlane (1,4-diicosa naphthalene-1,4-endoperoxide). Struct Chem 20, 399–407 (2009). https://doi.org/10.1007/s11224-009-9424-1

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