Chemical shift non-equivalence in the nmr spectroscopy of dialkyl α-hydroxybenzyl- and dialkyl α-methoxybenzylphosphonates and the crystal structure of dimethyl α-chloromethyl-α-hydroxybenzylphosphonate

Harry R. Hudson, Mary McPartlin, Ray W. Matthews, Harold R. Powell, Ramon O. Yusuf, Zsuzsa M. JáSzay, GyöRgy Keglevich, Imre PetneháZy, LáSzló TőKet

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Single crystal X-ray diffraction of dimethyl α-chloromethyl-α-hydroxybenzylphosphonate shows the compound to exist as hydrogen-bonded dimers in the solid state. In solution, 1H and 13C nmr spectroscopy reveal chemical shift non-equivalence of the corresponding nuclei in the two alkoxy groups of dialkyl α-hydroxybenzyl- and dialkyl α-methoxybenzylphosphonates, an effect that is attributed primarily to the presence of the chiral α-carbon atom, although restriction of rotation about the P-Cα bond by intermolecular hydrogen-bonding may also be a factor in the α-hydroxy compounds. Chemical shift non-equivalence of the α-halogenomethyl protons in dimethyl α-halogenomethyl-α-hydroxyben-zylphosphonates is significantly greater for the chloro- than for the bromo-compound.

Original languageEnglish
Pages (from-to)239-243
Number of pages5
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Issue number1-4
Publication statusPublished - jún. 1 1993


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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