Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks
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Intramolecular CF···FC interactions in selected organofluorine compounds (all-syn-1,2,3,4- and all-syn-1,2,4,5-tetrafluorocyclohexane, 1,8-difluoronaphthalene, 4,5-difluorophenanthrene, 2,2′,5,5′-tetrafluorobiphenyl) were studied at the MP2/aug-cc-pVDZ level using the recently developed noncovalent interaction (NCI) method. For the optimized minima, all CF···FC interactions that are identified by this method are classified as attractive, even in those cases where suitable isodesmic reaction energies fail to provide evidence for an energetic stabilization. Possible relations between these interactions and the observable JFF spin–spin coupling constant values are discussed.
Cormanich , R A , Rittner , R , O'Hagan , D & Buehl , M 2014 , ' Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks ' Journal of Physical Chemistry A , vol 118 , no. 36 , pp. 7901-7910 . DOI: 10.1021/jp504568c
Journal of Physical Chemistry A
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Physical Chemistry A., copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jp504568c
The authors thank EaStCHEM, the Royal Society (for a Wolfson Merit Award for D.O’H.) and CNPq and FAPESP are also gratefully acknowledged for the studentships (to R.A.C. #2011/01170-1, FAPESP), as is CNPq for the fellowship (R.R.).
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