Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives
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The assessment of weak inter- and intra- molecular Cδ+Fδ-...Cδ+=Oδ- interactions were theoretically evaluated in 4 different sets of compounds at different theoretical levels. Intermolecular CH3F...C=O interactions were stabilizing by ca. 1 kcal mol-1 for various carbonyl containing functional groups. Intramolecular CF...C=O interactions were also detected in aliphatic and fluorinated cyclohexane carbonyl derivatives. However, the stabilisation provided by intramolecular CF...C=O interactions was not enough to govern the conformational preferences of compounds 2-4.
Cormanich , R A , Rittner , R , O'Hagan , D & Buehl , M 2015 , ' Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives ' Journal of Computational Chemistry , vol In press . DOI: 10.1002/jcc.23918
Journal of Computational Chemistry
© 2015 Wiley Periodicals, Inc.This is the accepted version of the following article: R. A. Cormanich, R. Rittner, D. O'Hagan, M. Bühl. J. Comput. Chem. 2015, which has been published in final form at http://dx.doi.org/10.1002/jcc.23918.
The authors thank EaStCHEM and the University of St Andrews for access to a computing facility managed by Dr H. Fruchtl., CNPq, and FAPESP for the studentship (to R.A.C. #2011/01170-1, FAPESP) and for financial support (#2014/25903-6), as well as CNPq for the fellowship (R.R.).
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