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

Rodrigo Antonio Cormanich; Roberto Rittner; David O'Hagan; Michael Buehl

doi:10.1002/jcc.23918

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

Rodrigo Antonio Cormanich, Roberto Rittner, David O'Hagan, Michael Buehl

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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Abstract

The assessment of weak inter- and intra- molecular C^δ+F^δ-...C^δ+=O^δ- 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.

Original language	English
Journal	Journal of Computational Chemistry
Volume	In press
Early online date	23 Apr 2015
DOIs	https://doi.org/10.1002/jcc.23918
Publication status	Published - 2015

Keywords

Organofluorine compounds
Stereoelectronic effects
CF···C=O interactions

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10.1002/jcc.23918

pubRodrigo_CFCO-revised
© 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.
Accepted author manuscript, 286 KB

Novel organofluorine motifs: Novel organofluorine motifs in the service of industry
O'Hagan, D. (PI)
EPSRC
1/03/14 → 28/02/17
Project: Standard
Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry
O'Hagan, D. (PI)
EPSRC
31/07/10 → 1/08/10
Project: Standard

Cite this

@article{021328c00c9a4a57a7976d890f75d6d5,

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

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.",

keywords = "Organofluorine compounds, Stereoelectronic effects, CF···C=O interactions",

author = "Cormanich, {Rodrigo Antonio} and Roberto Rittner and David O'Hagan and Michael Buehl",

note = "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.). ",

year = "2015",

doi = "10.1002/jcc.23918",

language = "English",

volume = "In press",

journal = "Journal of Computational Chemistry",

issn = "1096-987X",

publisher = "John Wiley & Sons, Ltd",

}

TY - JOUR

T1 - Inter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives

AU - Cormanich, Rodrigo Antonio

AU - Rittner, Roberto

AU - O'Hagan, David

AU - Buehl, Michael

N1 - 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.).

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

KW - Organofluorine compounds

KW - Stereoelectronic effects

KW - CF···C=O interactions

U2 - 10.1002/jcc.23918

DO - 10.1002/jcc.23918

M3 - Article

SN - 1096-987X

VL - In press

JO - Journal of Computational Chemistry

JF - Journal of Computational Chemistry

ER -

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

Abstract

Keywords

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Projects

Novel organofluorine motifs: Novel organofluorine motifs in the service of industry

Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry

Cite this