Substituent effects on the ring-chain tautomerism of some 1,3-oxazolidine derivatives

Kalevi Pihlaja, Márta Juhász, Henri Kivelä, F. Fülöp

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The 14 and 70 eV electron ionization mass spectra of five sets (R 1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R 1-substituted (Ar = C6H4X; X = p-NO 2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar = C6H4X; X = m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable εRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3.

Original languageEnglish
Pages (from-to)1510-1518
Number of pages9
JournalRapid Communications in Mass Spectrometry
Volume22
Issue number10
DOIs
Publication statusPublished - May 2008

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Gases
Derivatives
Nuclear magnetic resonance spectroscopy
Ionization
Electrons
oxazolidine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

Cite this

Substituent effects on the ring-chain tautomerism of some 1,3-oxazolidine derivatives. / Pihlaja, Kalevi; Juhász, Márta; Kivelä, Henri; Fülöp, F.

In: Rapid Communications in Mass Spectrometry, Vol. 22, No. 10, 05.2008, p. 1510-1518.

Research output: Contribution to journalArticle

Pihlaja, Kalevi ; Juhász, Márta ; Kivelä, Henri ; Fülöp, F. / Substituent effects on the ring-chain tautomerism of some 1,3-oxazolidine derivatives. In: Rapid Communications in Mass Spectrometry. 2008 ; Vol. 22, No. 10. pp. 1510-1518.
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AB - The 14 and 70 eV electron ionization mass spectra of five sets (R 1 = Me, Et, i-Pr, t-Bu and Ph) of seven 2-aryl-4-R 1-substituted (Ar = C6H4X; X = p-NO 2, m-Br, p-Cl, H, p-Me, p-OMe and p-NMe2) (1-5) and of seven 2-aryl-5-phenyl-substituted 1,3-oxazolidines (6; for Ar, see above) were recorded to study their ring-chain equilibria in the gas phase. These equilibria were also studied by 1H NMR spectroscopy in CDCl3 for compounds 5 and 6. A few 2,4- and 2,5-dimethyl-2-aryl derivatives (7, 8: Ar = C6H4X; X = m-Br, H and p-OMe) were studied both in CDCl3 and in the gas phase. The main characteristics of the ring-chain equilibria expressed by the variable εRA% of the ring and of the chain form proved to be a strong dependence on the nature of the substituents on C-2 and C-4. The results in the gas phase are compared with those in CDCl3.

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