Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks

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.

Citation

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 . https://doi.org/10.1021/jp504568c

Publication

Journal of Physical Chemistry A

Status

Peer reviewed

DOI

https://doi.org/10.1021/jp504568c

ISSN

1089-5639

Type

Journal article

Rights

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

Description

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.).

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/7329