Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Mathew J. Jones; Ricardo Callejo; Alexandra M. Z. Slawin; Michael Bühl; David O'Hagan

doi:10.3762/bjoc.12.281

Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Mathew J. Jones, Ricardo Callejo, Alexandra M. Z. Slawin, Michael Bühl, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF₂ groups. The dipolar nature of the ring arises from the axial orientation of two of the C-F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF₂ groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.

Original language	English
Pages (from-to)	2823-2827
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.281
Publication status	Published - 22 Dec 2016

Keywords

Aliphatic rings
C-F bond
Cyclohexane conformation
Difluoromethylene group
Organofluorine chemistry

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10.3762/bjoc.12.281Licence: CC BY

O'Hagan_2016_BJOC_FacialPolarity_CC
© 2016 Jones et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 2.07 MBLicence: CC BY

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

Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring (dataset)
Jones, M. J. (Creator), Callejo, R. (Creator), Slawin, A. M. Z. (Creator), Buehl, M. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2017
https://dx.doi.org/10.5517/ccdc.csd.cc1mfydd
Dataset

Cite this

@article{9d3cc624dde44ab6ad62f282bf58c865,

title = "Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring",

abstract = "2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C-F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.",

keywords = "Aliphatic rings, C-F bond, Cyclohexane conformation, Difluoromethylene group, Organofluorine chemistry",

author = "Jones, {Mathew J.} and Ricardo Callejo and Slawin, {Alexandra M. Z.} and Michael B{\"u}hl and David O'Hagan",

note = "This work was supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea). D.O{\textquoteright}H. thanks the Royal Society for a Wolfson Research Merit Award.",

year = "2016",

month = dec,

day = "22",

doi = "10.3762/bjoc.12.281",

language = "English",

volume = "12",

pages = "2823--2827",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - Organofluorine chemistry

T2 - difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

AU - Jones, Mathew J.

AU - Callejo, Ricardo

AU - Slawin, Alexandra M. Z.

AU - Bühl, Michael

AU - O'Hagan, David

N1 - This work was supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea). D.O’H. thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2016/12/22

Y1 - 2016/12/22

N2 - 2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C-F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.

AB - 2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C-F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.

KW - Aliphatic rings

KW - C-F bond

KW - Cyclohexane conformation

KW - Difluoromethylene group

KW - Organofluorine chemistry

U2 - 10.3762/bjoc.12.281

DO - 10.3762/bjoc.12.281

M3 - Article

AN - SCOPUS:85008164832

SN - 1860-5397

VL - 12

SP - 2823

EP - 2827

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Abstract

Keywords

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

Datasets

Organofluorine chemistry: difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring (dataset)

Cite this