Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes

Cihang Yu; Bruno A. Piscelli; Nawaf Al Maharik; David B. Cordes; Alexandra M. Z. Slawin; Rodrigo A. Cormanich; David O'Hagan

doi:10.1039/D2CC05058G

Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes

Cihang Yu, Bruno A. Piscelli, Nawaf Al Maharik, David B. Cordes, Alexandra M. Z. Slawin, Rodrigo A. Cormanich^*, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

Theory and solution NMR indicate that all-syn 1,3,5-trifluorocyclohexane 5 adopts the expected tri-equatorial conformation, however in the solid state the more polar triaxial conformation is observed. This and the favoured conformations of substituted (Me, OMe, NH(CO)Me, NHBoc) derivatives of 5 are investigated to explore triaxial C–F preferences.

Original language	English
Pages (from-to)	12855-12858
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	92
Early online date	25 Oct 2022
DOIs	https://doi.org/10.1039/D2CC05058G
Publication status	Published - 28 Nov 2022

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Copyright © The Author(s) 2022. Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 1.13 MBLicence: CC BY

CCDC 2202377 - 2202382: Experimental Crystal Structure Determination
Yu, C. (Creator), Piscelli, B. A. (Creator), Al Maharik, N. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Cormanich, R. A. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2cxrfh, https://dx.doi.org/10.5517/ccdc.csd.cc2cxrgj and 4 more links, https://dx.doi.org/10.5517/ccdc.csd.cc2cxrhk, https://dx.doi.org/10.5517/ccdc.csd.cc2cxrjl, https://dx.doi.org/10.5517/ccdc.csd.cc2cxrkm, https://dx.doi.org/10.5517/ccdc.csd.cc2cxrln (show fewer)
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@article{44ce1bd479d44698978630e9d968bfd7,

title = "Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes",

abstract = "Theory and solution NMR indicate that all-syn 1,3,5-trifluorocyclohexane 5 adopts the expected tri-equatorial conformation, however in the solid state the more polar triaxial conformation is observed. This and the favoured conformations of substituted (Me, OMe, NH(CO)Me, NHBoc) derivatives of 5 are investigated to explore triaxial C–F preferences.",

author = "Cihang Yu and Piscelli, {Bruno A.} and Maharik, {Nawaf Al} and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Cormanich, {Rodrigo A.} and David O'Hagan",

note = "Funding: Authors thank the Chinese Scholarship Council and FAPESP for studentships (BAP, #2021/09716-5) a Young Researcher Award (RAC, #2018/03910-1) and FAEPEX for a fellowship (RAC, #2479/21).",

year = "2022",

month = nov,

day = "28",

doi = "10.1039/D2CC05058G",

language = "English",

volume = "58",

pages = "12855--12858",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "92",

}

TY - JOUR

T1 - Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes

AU - Yu, Cihang

AU - Piscelli, Bruno A.

AU - Maharik, Nawaf Al

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Cormanich, Rodrigo A.

AU - O'Hagan, David

N1 - Funding: Authors thank the Chinese Scholarship Council and FAPESP for studentships (BAP, #2021/09716-5) a Young Researcher Award (RAC, #2018/03910-1) and FAEPEX for a fellowship (RAC, #2479/21).

PY - 2022/11/28

Y1 - 2022/11/28

N2 - Theory and solution NMR indicate that all-syn 1,3,5-trifluorocyclohexane 5 adopts the expected tri-equatorial conformation, however in the solid state the more polar triaxial conformation is observed. This and the favoured conformations of substituted (Me, OMe, NH(CO)Me, NHBoc) derivatives of 5 are investigated to explore triaxial C–F preferences.

AB - Theory and solution NMR indicate that all-syn 1,3,5-trifluorocyclohexane 5 adopts the expected tri-equatorial conformation, however in the solid state the more polar triaxial conformation is observed. This and the favoured conformations of substituted (Me, OMe, NH(CO)Me, NHBoc) derivatives of 5 are investigated to explore triaxial C–F preferences.

U2 - 10.1039/D2CC05058G

DO - 10.1039/D2CC05058G

M3 - Article

SN - 1359-7345

VL - 58

SP - 12855

EP - 12858

JO - Chemical Communications

JF - Chemical Communications

IS - 92

ER -

Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes

Abstract

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Datasets

CCDC 2202377 - 2202382: Experimental Crystal Structure Determination

Cite this