Gas-Phase Ring-Chain Tautomerism in 1,3-oxazolidines

Pirjo Vainiotalo, Sari Ronkanen, Ferenc Fülöp, Kalevi Pihlaja

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Abstract

Gas-phase ring-chain tautomeric equilibria with fourteen 1,3-oxazolidines derived from norephedrine and norpseudoephedrine were studied by means of mass spectrometry. Using 14 eV ionizing electrons these equilibria were comparable to those in non-polar solvent and obeyed the simple equation: log Kx = ρ σ+ + c, where ρ = 0.58±0.06 and 0.55+0.03 and c = 0.14+0.05 and 0.30±0.03 for norephedrine and norpseudoephedrine derivatives, respectively. Approximate values of enthalpy differences were also observed.

Original languageEnglish
Pages (from-to)3683-3692
Number of pages10
JournalTetrahedron
Volume46
Issue number10
DOIs
Publication statusPublished - 1990

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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