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

Rodrigo A. Cormanich; Roberto Rittner; David O'Hagan; Michael Buehl

doi:10.1021/jp504568c

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

Rodrigo A. Cormanich, Roberto Rittner, David O'Hagan^*, Michael Buehl

^*Corresponding author for this work

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

Abstract

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 J_FF spin–spin coupling constant values are discussed.

Original language	English
Pages (from-to)	7901-7910
Number of pages	10
Journal	Journal of Physical Chemistry A
Volume	118
Issue number	36
Early online date	26 Aug 2014
DOIs	https://doi.org/10.1021/jp504568c
Publication status	Published - 11 Sept 2014

Keywords

Nuclear-magnetic-resonance
Spin coupling-constants
Intermolecular interactions
Organofluorine chemistry
Molecular-structure
Electron-density
Fluorine
Bond
NMR
Atoms

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10.1021/jp504568c

OHagan_2014_JPCA_Analysis_AM
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
Accepted author manuscript, 1.05 MB

Novel organofluorine motifs: Novel organofluorine motifs in the service of industry
O'Hagan, D. (PI)
EPSRC
1/03/14 → 28/02/17
Project: Standard
CF2 Group: The CF2 group as a conformational tool in the olfactory receptor response
O'Hagan, D. (PI)
EPSRC
20/05/13 → 19/05/16
Project: Standard

Cite this

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title = "Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks",

abstract = "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.",

keywords = "Nuclear-magnetic-resonance, Spin coupling-constants, Intermolecular interactions, Organofluorine chemistry, Molecular-structure, Electron-density, Fluorine, Bond, NMR, Atoms",

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

note = "The authors thank EaStCHEM, the Royal Society (for a Wolfson Merit Award for D.O{\textquoteright}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.). ",

year = "2014",

month = sep,

day = "11",

doi = "10.1021/jp504568c",

language = "English",

volume = "118",

pages = "7901--7910",

journal = "Journal of Physical Chemistry A",

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publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Analysis of CF···FC interactions on cyclohexane and naphthalene frameworks

AU - Cormanich, Rodrigo A.

AU - Rittner, Roberto

AU - O'Hagan, David

AU - Buehl, Michael

N1 - 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.).

PY - 2014/9/11

Y1 - 2014/9/11

N2 - 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.

AB - 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.

KW - Nuclear-magnetic-resonance

KW - Spin coupling-constants

KW - Intermolecular interactions

KW - Organofluorine chemistry

KW - Molecular-structure

KW - Electron-density

KW - Fluorine

KW - Bond

KW - NMR

KW - Atoms

U2 - 10.1021/jp504568c

DO - 10.1021/jp504568c

M3 - Article

SN - 1089-5639

VL - 118

SP - 7901

EP - 7910

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 36

ER -

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

Abstract

Keywords

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Projects

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

CF2 Group: The CF2 group as a conformational tool in the olfactory receptor response

Cite this