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Effect of transannular interaction on the redox-potentials in a series of bicyclic quinones

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Effect of transannular interaction on the redox-potentials in a series of bicyclic quinones Page 1 of (page number not for citation purposes) 8 Effect of transannular interaction on the redox- potentials in a series of bicyclic quinones Grigoriy Sereda*, Jesse Van Heukelom, Miles Koppang, Sudha Ramreddy and Nicole Collins Full Research Paper Open Access Address: The University of South Dakota, Department of Chemistry 414 E. Clark St., Vermillion, SD 57069, USA Email: Grigoriy Sereda* -; Jesse Van Heukelom -; Miles Koppang -; Sudha Ramreddy -; Nicole Collins - * Corresponding author Beilstein Journal of Organic Chemistry 2006, 2, No. 26. doi:10.1186/1860-5397-2-26 Received: 08 November 2006 Accepted: 08 December 2006 Published: 08 December 2006 © 2006 Sereda et al; licensee Beilstein-Institut. License and terms: see end of document. Abstract Background Better understanding of the transannular influence of a substituent on the redox-potentials of bicyclo[2.2.2]octane-derived quinones will help in the design of new compounds with controlled biological activity. However, attempts to directly relate the reduction potentials of substituted triptycene-quinones to the electronic effects of substituents are often unsuccessful. Results First and second redox-potentials of a series of bicyclic quinones are compared to computed energies of their LUMO, LUMO+1, and energies of reduction. Transannular influence of substituent on the redox-potentials is rationalized in terms of MO theory. Acetoxy-substituents in the 5,8-positions of the triptycene-quinone system selectively destabilize the product of the two-electron reduction. Conclusion We have shown that first redox-potentials of substituted bicyclic quinones correlate with their calculated LUMO energies and the energies of reduction. The second redox-potentials correlate with calculated LUMO+1 energies. As opposed to the LUMO orbitals, the LUMO+1

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