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

Research output: Contribution to journalArticlepeer-review


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 languageEnglish
Article number50
Issue number2
Publication statusPublished - Feb 2023
Externally publishedYes


  • carboxylic acid
  • hydrogen bond
  • phosphonium ylide
  • X-ray structure


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