1 H and  13 C NMR study of the enol–enolic tautomerism of some cyclic β‐ketoaldehydes | Zendy

Shapet'ko N. N. | Zendy; Radushnova I. L. | Zendy; Bogachev Yu. S. | Zendy; Berestova S. S. | Zendy; Potapov V. M. | Zendy; Kiryuschkina G. V. | Zendy; Talebarovskaya I. K. | Zendy

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1 H and 13 C NMR study of the enol–enolic tautomerism of some cyclic β‐ketoaldehydes

Author(s) -

Shapet'ko N. N.,

Radushnova I. L.,

Bogachev Yu. S.,

Berestova S. S.,

Potapov V. M.,

Kiryuschkina G. V.,

Talebarovskaya I. K.

Publication year - 1975

Publication title -

organic magnetic resonance

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0030-4921

DOI - 10.1002/mrc.1270071104

Subject(s) - tautomer , chemistry , chemical shift , enol , aldehyde , enthalpy , keto–enol tautomerism , ketone , computational chemistry , stereochemistry , organic chemistry , physics , thermodynamics , catalysis

Aldehyde (δCH) and enolic (δOH) proton chemical shifts, the corresponding spin–spin coupling constants ( J CH,OH) and the 13 C chemical shifts (δC) have been measured for three cyclic β‐ketoaldehydes as a function of temperature. A tautomeric equilibrium has been shown to exist between the aldo–enol ( A ) and hydroxymethylene ketone ( B ) forms. The chemical shifts δCH δOH and δC for the two pure tautomeric forms A and B have been calculated. The enthalpy changes Δ H in the tautomeric process A ⇄ B and the percentages of the tautomeric forms have been determined.

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