NMR and symmetry in bisphosphonates R1R2N-CH[P(O)(OMe)2]2

Nader Amadeu, Erika Bálint, Winfried Boenigk, Ádám Tajti, Gerhard Hägele, Christoph Janiak, G. Keglevich

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

(Amino-methylene)bisphosphonates R1R2N-CH[P(O)(OMe)2]2 bearing achiral and chiral substituents (R1 = Ph, R2 = H, Me; and R1 = PhCH(Me), R2 = Me, Bn) were synthesized and characterized in CDCl3 by 1H, 1H{31P}, 13C{1H}, 31P{1H}, and 31P NMR spectra. [P(O)(OMe)2]2 fragments from achiral compounds give rise to complex 1H NMR spectra characteristic for the [A3M3X]2 1H NMR spectra while chiral compounds yield A3G3M3T3XY type spectra. Aspects of molecular symmetry governing the multiplet patterns are discussed and precise spectral parameters are calculated by line-shape iterations.

Original languageEnglish
Pages (from-to)643-650
Number of pages8
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume192
Issue number6
DOIs
Publication statusPublished - Jun 3 2017

Keywords

  • (Amino-methylene)bisphosphonates
  • grid net search
  • line-shape iterations
  • methyl esters
  • multinuclear NMR
  • spin systems

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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