Oxo-Stabilised Phosphonium Ylides as Hydrogen Bond Acceptors

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 C-13 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.

Automated summary

Oxo-stabilised phosphonium ylides can form crystalline hydrogen-bonded adducts with aromatic carboxylic acids, as evidenced by X-ray diffraction. C-13 NMR spectroscopy also confirms strong hydrogen bonding in solution with acetic acid, benzamide, thiobenzamide, benzyl alcohol, benzenesulfinic acid, and diphenylphosphinic acid. The X-ray structure of the benzamide adduct reveals a hydrogen-bonded dimeric structure. A bis(stabilised ylide) can also form a complex hydrogen-bonded adduct with benzoic acid, ethanol, and water.