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Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives

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pubRodrigo_CFCO_revised.pdf (286.1Kb)
Date
2015
Author
Cormanich, Rodrigo Antonio
Rittner, Roberto
O'Hagan, David
Buehl, Michael
Keywords
Organofluorine compounds
Stereoelectronic effects
CF···C=O interactions
QD Chemistry
NDAS
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Abstract
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.
Citation
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 . https://doi.org/10.1002/jcc.23918
Publication
Journal of Computational Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/jcc.23918
ISSN
1096-987X
Type
Journal article
Rights
© 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.
Description
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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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/8669

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