On the existence of the elusive monomethyl ester of carbonic acid [CH 3OC(O)OH] at 300 K: 1H- and 13C NMR measurements and DFT calculations

Angela Dibenedetto, Michele Aresta, Potenzo Giannoccaro, Carlo Pastore, I. Pápai, G. Schubert

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The elusive monomethyl ester of carbonic acid [CH3OC(O)-OH] has been prepared at 300 K by protonation of the sodium salt NaOC(O)OCH3 with anhydrous HCl or water and characterized by 1H- and 13C NMR spectroscopy. The stability of the acid and its reactivity towards hydroxo ions and methylating agents under ambient conditions are discussed. The energetics and the mechanism of the investigated reactions are examined on the basis of density functional calculations. For kinetic and thermodynamic reasons CH3OC(O)OH is unlikely to be formed by insertion of CO2 into the O-H bond of methanol.

Original languageEnglish
Pages (from-to)908-913
Number of pages6
JournalEuropean Journal of Inorganic Chemistry
Issue number5
DOIs
Publication statusPublished - Mar 6 2006

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Carbonic Acid
Protonation
Discrete Fourier transforms
Nuclear magnetic resonance spectroscopy
Density functional theory
Methanol
Esters
Salts
Sodium
Nuclear magnetic resonance
Thermodynamics
Ions
Kinetics
Acids
Water

Keywords

  • Carbon dioxide
  • Density functional calculations
  • Methylation
  • NMR spectroscopy

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

On the existence of the elusive monomethyl ester of carbonic acid [CH 3OC(O)OH] at 300 K : 1H- and 13C NMR measurements and DFT calculations. / Dibenedetto, Angela; Aresta, Michele; Giannoccaro, Potenzo; Pastore, Carlo; Pápai, I.; Schubert, G.

In: European Journal of Inorganic Chemistry, No. 5, 06.03.2006, p. 908-913.

Research output: Contribution to journalArticle

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