Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors

R. Alan Aitken; Lee P. Cleghorn; Graham Dawson; Ian P. Gray; Anna Lashtabeg; Alexandra M.Z. Slawin

doi:10.3390/inorganics11020050

Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors

R. Alan Aitken^*, Lee P. Cleghorn, Graham Dawson, Ian P. Gray, Anna Lashtabeg, Alexandra M.Z. Slawin

^*Corresponding author for this work

University of St Andrews

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

Abstract

Oxo-stabilised phosphonium ylides are found to form crystalline hydrogen-bonded adducts with aromatic carboxylic acids, as confirmed by X-ray diffraction. There is also strong hydrogen bonding in solution as indicated by ¹³C NMR spectroscopy and this confirmed adduct formation with acetic acid, benzamide, thiobenzamide, benzyl alcohol, benzenesulfinic acid and diphenylphosphinic acid. The X-ray structure of the benzamide adduct was also determined, showing a hydrogen-bonded dimeric structure. A bis(stabilised ylide) was also prepared and is found to form a complex hydrogen-bonded adduct with benzoic acid, ethanol and water.

Original language	English
Article number	50
Journal	Inorganics
Volume	11
Issue number	2
DOIs	https://doi.org/10.3390/inorganics11020050
Publication status	Published - Feb 2023
Externally published	Yes

Keywords

carboxylic acid
hydrogen bond
phosphonium ylide
X-ray structure

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10.3390/inorganics11020050

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title = "Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors",

abstract = "Oxo-stabilised phosphonium ylides are found to form crystalline hydrogen-bonded adducts with aromatic carboxylic acids, as confirmed by X-ray diffraction. There is also strong hydrogen bonding in solution as indicated by 13C NMR spectroscopy and this confirmed adduct formation with acetic acid, benzamide, thiobenzamide, benzyl alcohol, benzenesulfinic acid and diphenylphosphinic acid. The X-ray structure of the benzamide adduct was also determined, showing a hydrogen-bonded dimeric structure. A bis(stabilised ylide) was also prepared and is found to form a complex hydrogen-bonded adduct with benzoic acid, ethanol and water.",

keywords = "carboxylic acid, hydrogen bond, phosphonium ylide, X-ray structure",

author = "Aitken, {R. Alan} and Cleghorn, {Lee P.} and Graham Dawson and Gray, {Ian P.} and Anna Lashtabeg and Slawin, {Alexandra M.Z.}",

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doi = "10.3390/inorganics11020050",

language = "English",

volume = "11",

journal = "Inorganics",

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TY - JOUR

T1 - Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors

AU - Aitken, R. Alan

AU - Cleghorn, Lee P.

AU - Dawson, Graham

AU - Gray, Ian P.

AU - Lashtabeg, Anna

AU - Slawin, Alexandra M.Z.

PY - 2023/2

Y1 - 2023/2

N2 - Oxo-stabilised phosphonium ylides are found to form crystalline hydrogen-bonded adducts with aromatic carboxylic acids, as confirmed by X-ray diffraction. There is also strong hydrogen bonding in solution as indicated by 13C NMR spectroscopy and this confirmed adduct formation with acetic acid, benzamide, thiobenzamide, benzyl alcohol, benzenesulfinic acid and diphenylphosphinic acid. The X-ray structure of the benzamide adduct was also determined, showing a hydrogen-bonded dimeric structure. A bis(stabilised ylide) was also prepared and is found to form a complex hydrogen-bonded adduct with benzoic acid, ethanol and water.

AB - Oxo-stabilised phosphonium ylides are found to form crystalline hydrogen-bonded adducts with aromatic carboxylic acids, as confirmed by X-ray diffraction. There is also strong hydrogen bonding in solution as indicated by 13C NMR spectroscopy and this confirmed adduct formation with acetic acid, benzamide, thiobenzamide, benzyl alcohol, benzenesulfinic acid and diphenylphosphinic acid. The X-ray structure of the benzamide adduct was also determined, showing a hydrogen-bonded dimeric structure. A bis(stabilised ylide) was also prepared and is found to form a complex hydrogen-bonded adduct with benzoic acid, ethanol and water.

KW - carboxylic acid

KW - hydrogen bond

KW - phosphonium ylide

KW - X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=85148751580&partnerID=8YFLogxK

U2 - 10.3390/inorganics11020050

DO - 10.3390/inorganics11020050

M3 - Article

AN - SCOPUS:85148751580

SN - 2304-6740

VL - 11

JO - Inorganics

JF - Inorganics

IS - 2

M1 - 50

ER -

Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors

Abstract

Keywords

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