Synthesis and structure of stable water-soluble phosphonium alkanoate zwitterions derived from 1,3,5-triaza-7-phosphaadamantane

Antal Udvardy, Mihály Purgel, Tímea Szarvas, Ferenc Joó, Ágnes Kathó

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

1,3,5-triaza-7-phosphaadamantane (PTA) was shown to form phosphonium alkanoate zwitterions with unsaturated dicarboxylic acids in water in the absence of strong acids. Solid-state structures of the phosphonium salt (1) derived from maleic or fumaric acids and that of the zwitterionic product (2) of the reaction of PTA with citraconic and mesaconic acids were determined by single-crystal X-ray diffraction. DFT calculations gave insight into the mechanism of the reaction, including the relative reactivity of the four dicarboxylic acids, and revealed the reasons for the lack of phosphonium salt formation by PTA in strongly acidic aqueous solutions.

Original languageEnglish
Pages (from-to)1323-1334
Number of pages12
JournalStructural Chemistry
Volume26
Issue number5-6
DOIs
Publication statusPublished - Dec 1 2015

Keywords

  • 1,3,5-triaza-7-phosphaadamantane
  • Fumaric acid
  • Maleic acid
  • Phosphonium salt
  • Water-soluble
  • Zwitterion

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Synthesis and structure of stable water-soluble phosphonium alkanoate zwitterions derived from 1,3,5-triaza-7-phosphaadamantane'. Together they form a unique fingerprint.

  • Cite this