Tautomerism of N-(2-Bromo-3-ethoxypropyl)-Nʹ-trifluoromethylsulfonylacetamidine

• Published in: Russian journal of general chemistry Vol. 91; no. 4; pp. 657 - 660
• Main Authors: Shainyan, B. A., Chipanina, N. N., Oznobikhina, L. P., Ganin, A. S.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-04-2021; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Dimethyl sulfoxide; Infrared spectroscopy; NMR spectroscopy; tautomerism; ′; (trifluoromethylsulfonyl)ethaneimidamide; (; quantum chemical calculations; NMR spectroscopy; 2-bromo-3-ethoxypropyl; IR spectroscopy
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363221040125

Depending on the solvent nature,
N
(
N
′)-(2-bromo-3-ethoxypropyl)-
N
′(
N
)-(trifluoromethylsulfonyl)ethaneimidamide exists in two tautomeric forms: RNH–C(Me)=NTf and RN=C(Me)–NHTf. The shift of the tautomeric equilibrium from the more stable RNH–C(Me)=NTf to the less stable RN=C(Me)–NHTf in the solution in dimethyl sulfoxide and trifluoroethanol was shown by IR and NMR spectroscopy.