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American Chemical Society, The Journal of Physical Chemistry A, 7(110), p. 2517-2526, 2006

DOI: 10.1021/jp0562835

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Ortho Effect in the Bergman Cyclization: Electronic and Steric Effects in Hydrogen Abstraction by 1-Substituted Naphthalene 5,8-Diradicals

Journal article published in 2006 by Frank C. Pickard ORCID, Rebecca L. Shepherd, Amber E. Gillis, Meghan E. Dunn, Steven Feldgus, Karl N. Kirschner, George C. Shields, Mariappan Manoharan, Igor V. Alabugin
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This paper is available in a repository.

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Abstract

We present a detailed theoretical study of geometries, electronic structure, and energies of transition states and intermediates completing the full Bergman cycloaromatization pathway of ortho-substituted enediynes with a focus on polar and steric contributions to the kinetics and thermodynamics of hydrogen abstraction. This study provides a rare unambiguous example of remote substitution that affects reactivity of a neutral reactive intermediate through an sigma framework.