2,3-Bisphosphonosuccinic Acid Hexamethyl Ester [(CH 3O) 2(O)P-CH-COOCH 3] 2-NMR-Spectroscopic Studies of ABX and [AM 3R 3X] 2+Z 6 Spin Systems

Gerhard Hägele, Joachim Dettmann, Krzysztof Huben, Stefan Jankowski, Erika Bálint, G. Keglevich

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Addition of dimethyl phosphite to the triple bond of dimethylacetylene-dicarboxylate by conventional routes or assisted by microwaves leads predominantly to the meso form of 2,3-bisphosphonosuccinic acid hexamethyl ester [(CH3O)2(O)P-CH-COOCH3]2. Molecular structure and dominant rotamer were deduced from multinuclear 31P{1H}-, 13C{1H}-, 1H-, 1H{31P}-NMR studies on ABX and [AM3R3X]2+Z6 spin systems. Vicinal coupling constants 3JPP, 3JPH, and 3JHH were used as stereochemically relevant parameters to deduce rotamer preferences via Karplus-type relationships.

Original languageEnglish
Pages (from-to)1315-1327
Number of pages13
JournalPhosphorus, Sulfur and Silicon and Related Elements
Volume189
Issue number9
DOIs
Publication statusPublished - Sep 2 2014

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Microwaves
Molecular Structure
Molecular structure
Esters
Nuclear magnetic resonance
Acids
dimethyl hydrogen phosphite
dimethylacetylene
Proton Magnetic Resonance Spectroscopy

Keywords

  • 2,3-bisphosphonosuccinate
  • 2-ethane-bisphosphonate
  • C{H}
  • H
  • H{P}
  • P{H}
  • JPP
  • ABX
  • Meso 1
  • spectral analysis
  • [AMRX]2+Z

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

2,3-Bisphosphonosuccinic Acid Hexamethyl Ester [(CH 3O) 2(O)P-CH-COOCH 3] 2-NMR-Spectroscopic Studies of ABX and [AM 3R 3X] 2+Z 6 Spin Systems. / Hägele, Gerhard; Dettmann, Joachim; Huben, Krzysztof; Jankowski, Stefan; Bálint, Erika; Keglevich, G.

In: Phosphorus, Sulfur and Silicon and Related Elements, Vol. 189, No. 9, 02.09.2014, p. 1315-1327.

Research output: Contribution to journalArticle

Hägele, Gerhard ; Dettmann, Joachim ; Huben, Krzysztof ; Jankowski, Stefan ; Bálint, Erika ; Keglevich, G. / 2,3-Bisphosphonosuccinic Acid Hexamethyl Ester [(CH 3O) 2(O)P-CH-COOCH 3] 2-NMR-Spectroscopic Studies of ABX and [AM 3R 3X] 2+Z 6 Spin Systems. In: Phosphorus, Sulfur and Silicon and Related Elements. 2014 ; Vol. 189, No. 9. pp. 1315-1327.
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AU - Hägele, Gerhard

AU - Dettmann, Joachim

AU - Huben, Krzysztof

AU - Jankowski, Stefan

AU - Bálint, Erika

AU - Keglevich, G.

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