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RESEARCH PRODUCT
Long-range substituent and temperature effect on prototropic tautomerism in 2-(acylmethyl)quinolines
Erkki KolehmainenRyszard GawineckiReijo KauppinenBorys Ośmiałowskisubject
StereochemistryHydrogen bondOrganic ChemistryQuinolineSubstituentElectron donorCarbon-13 NMRConjugated systemMedicinal chemistryTautomerchemistry.chemical_compoundchemistryProton NMRPhysical and Theoretical Chemistrydescription
Tautomeric equilibria between 2-(cinnamoylmethyl)quinoline, (Z)-1,2-dihydro-2-(cinnamoylmethylene)quinoline and (Z)-4-phenyl-1-(2-quinolyl)-1,3-butadien-2-ol were studied by 1H, 13C and 15N NMR methods. The —CHCH— fragment conjugated with phenyl and a strong electron donor p-(1-pyrrolidine) substituent were found to favour the enolimine tautomer. This undergoes fast exchange (on the NMR time-scale) with the enaminone form. The amount of the latter tautomer was found to increase at low temperatures. Copyright © 2001 John Wiley & Sons, Ltd.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-01-01 | Journal of Physical Organic Chemistry |