Structural Chemistry

, Volume 14, Issue 4, pp 391–397 | Cite as

The Molecular Structure and NMR Properties of P-Phosphinoylmethyl Aminophosphonium Salts

  • Carmen López-Leonardo
  • Mateo Alajarín
  • Pilar Llamas-Lorente
  • Delia Bautista
  • María Luisa Jimeno
  • Ibon Alkorta
  • José Elguero

Abstract

The molecular structures of two aminophosphonium salts (bromide and tetrafluoroborate) have been determined by X-ray analysis. They have similar conformations and hydrogen bond (HB) networks: the N–H acid proton is bonded to the anion and, in the case of the fluoroborate, to the oxygen atom of the phosphine oxide, forming a pseudo six-membered ring closed by a weak N–H⋅⋅⋅O intramolecular hydrogen bond (IMHB). These compounds have been studied by multinuclear NMR in solution, including the 15N-labeled derivatives, to determine a complete set of coupling constants. A coupling of ∣1.5∣ Hz between the 15N and the 31P nuclei, separated by three bonds, was observed experimentally for the bromide in CDCl3 solution, which appears to be a classical 3JN-P across the covalent bonds and not a 3hJN-P across the IMHB.

Coupling constants intramolecular hydrogen bonds 15N-labeled derivatives aminophosphonium salts 

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Copyright information

© Plenum Publishing Corporation 2003

Authors and Affiliations

  • Carmen López-Leonardo
    • 1
  • Mateo Alajarín
    • 1
  • Pilar Llamas-Lorente
    • 1
  • Delia Bautista
    • 2
  • María Luisa Jimeno
    • 3
  • Ibon Alkorta
    • 3
  • José Elguero
    • 3
  1. 1.Departamento de Química Orgánica, Facultad de QuímicaUniversidad de MurciaMurciaSpain
  2. 2.Servicio Universitario de Instrumentación Científica, Edificio SACEUniversidad de MurciaMurciaSpain
  3. 3.Instituto de Química MédicaCentro de Química Orgánica ‘Manuel Lora Tamayo,’ CSICMadridSpain

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