Bis(alkyl)thioethers on a biphenyl scaffold: a spectroscopic and structural insight

Rhiann Ferguson; Phillip S. Nejman; Alexandra M. Z. Slawin; J. Derek Woollins

doi:10.1016/j.molstruc.2017.04.108

Bis(alkyl)thioethers on a biphenyl scaffold: a spectroscopic and structural insight

Rhiann Ferguson, Phillip S. Nejman, Alexandra M. Z. Slawin, J. Derek Woollins

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

Abstract

A series of bis(alkyl)thioether compounds utilising biphenyl as the backbone of the type 2,2′-bis(alkylthio)-1,1′-biphenyl have been prepared with yields of 32-70%. The six benzyl derivatives all displayed an AB quartet for the CH₂ hydrogens within their ¹H NMR spectra due to restricted rotation within the molecule. Where the alkyl group was changed to neopentyl the CH₂protons became equivalent giving rise to a singlet within the ¹H NMR spectrum. The compounds have been characterised principally using multinuclear NMR spectroscopy and single crystal X-ray diffraction.

Original language	English
Pages (from-to)	405-414
Journal	Journal of Molecular Structure
Volume	1143
Early online date	2 May 2017
DOIs	https://doi.org/10.1016/j.molstruc.2017.04.108
Publication status	Published - 5 Sept 2017

Keywords

Thioether
Sulfur
Biphenyl
NMR spectroscopy
X-ray structure

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Woollins_2017_JMS_Thioether_AAM
© 2017 Elsevier Ltd. All rights reserved. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.molstruc.2017.04.108
Accepted author manuscript, 1.17 MBLicence: CC BY-NC-ND
Woollins_2017_JMS_Thioether_AAM_supplementaryAccepted author manuscript, 1.16 MBLicence: CC BY-NC-ND

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@article{707d0a761f3544e98fc937963de3c898,

title = "Bis(alkyl)thioethers on a biphenyl scaffold: a spectroscopic and structural insight",

abstract = "A series of bis(alkyl)thioether compounds utilising biphenyl as the backbone of the type 2,2′-bis(alkylthio)-1,1′-biphenyl have been prepared with yields of 32-70\%. The six benzyl derivatives all displayed an AB quartet for the CH2 hydrogens within their 1H NMR spectra due to restricted rotation within the molecule. Where the alkyl group was changed to neopentyl the CH2 protons became equivalent giving rise to a singlet within the 1H NMR spectrum. The compounds have been characterised principally using multinuclear NMR spectroscopy and single crystal X-ray diffraction.",

keywords = "Thioether, Sulfur, Biphenyl, NMR spectroscopy, X-ray structure",

author = "Rhiann Ferguson and Nejman, \{Phillip S.\} and Slawin, \{Alexandra M. Z.\} and Woollins, \{J. Derek\}",

year = "2017",

month = sep,

day = "5",

doi = "10.1016/j.molstruc.2017.04.108",

language = "English",

volume = "1143",

pages = "405--414",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

}

TY - JOUR

T1 - Bis(alkyl)thioethers on a biphenyl scaffold

T2 - a spectroscopic and structural insight

AU - Ferguson, Rhiann

AU - Nejman, Phillip S.

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

PY - 2017/9/5

Y1 - 2017/9/5

N2 - A series of bis(alkyl)thioether compounds utilising biphenyl as the backbone of the type 2,2′-bis(alkylthio)-1,1′-biphenyl have been prepared with yields of 32-70%. The six benzyl derivatives all displayed an AB quartet for the CH2 hydrogens within their 1H NMR spectra due to restricted rotation within the molecule. Where the alkyl group was changed to neopentyl the CH2 protons became equivalent giving rise to a singlet within the 1H NMR spectrum. The compounds have been characterised principally using multinuclear NMR spectroscopy and single crystal X-ray diffraction.

AB - A series of bis(alkyl)thioether compounds utilising biphenyl as the backbone of the type 2,2′-bis(alkylthio)-1,1′-biphenyl have been prepared with yields of 32-70%. The six benzyl derivatives all displayed an AB quartet for the CH2 hydrogens within their 1H NMR spectra due to restricted rotation within the molecule. Where the alkyl group was changed to neopentyl the CH2 protons became equivalent giving rise to a singlet within the 1H NMR spectrum. The compounds have been characterised principally using multinuclear NMR spectroscopy and single crystal X-ray diffraction.

KW - Thioether

KW - Sulfur

KW - Biphenyl

KW - NMR spectroscopy

KW - X-ray structure

UR - http://www.sciencedirect.com/science/article/pii/S0022286017305604#appd001

UR - https://www.scopus.com/pages/publications/85018781512

U2 - 10.1016/j.molstruc.2017.04.108

DO - 10.1016/j.molstruc.2017.04.108

M3 - Article

SN - 0022-2860

VL - 1143

SP - 405

EP - 414

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

ER -

Bis(alkyl)thioethers on a biphenyl scaffold: a spectroscopic and structural insight

Abstract

Keywords

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