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RESEARCH PRODUCT
Predominance of 2-arylhydrazones of 1,3-diphenylpropane-1,2,3-trione over its proton-transfer products
Reijo KauppinenBorys OśmiałowskiRyszard GawineckiErkki KolehmainenHenryk JanotaMaija Nissinensubject
chemistry.chemical_classificationChloroformHydrogen bondChemical shiftOrganic ChemistrySubstituentHydrazoneTautomerchemistry.chemical_compoundchemistryComputational chemistryAb initio quantum chemistry methodsMoietyPhysical and Theoretical Chemistrydescription
2-Phenylhydrazones of 1,3-diphenyl-1,2,3-trione are the dominant tautomeric form detected in chloroform solution by 15N NMR chemical shifts. The substituent in the phenylhydrazone moiety does not affect this tautomeric preference. The substituent effect is transmitted effectively only to the hydrazone nitrogen and hydrogen atoms. Ab initio calculations show that the ketohydrazone tautomer is really very much favoured over its proton-transfer products in chloroform solution. The same tautomer was also detected in the crystal state by X-ray crystallography. Copyright © 2001 John Wiley & Sons, Ltd.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-01-01 | Journal of Physical Organic Chemistry |