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Structures of Hemi‐Curcuminoids in the Solid State and in Solution
Author(s) -
Cornago Pilar,
Cabildo Pilar,
Sanz Dionisia,
Claramunt Rosa M.,
Torralba M. Carmen,
Torres M. Rosario,
Elguero José
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300488
Subject(s) - chemistry , tautomer , moiety , enol , keto–enol tautomerism , scavenger , solid state , curcumin , diketone , proton nmr , proton , photochemistry , antioxidant , organic chemistry , catalysis , biochemistry , physics , quantum mechanics
Abstract Hemi‐curcuminoids are derivatives of the antioxidant radical scavenger curcumin in which one styryl moiety is missing but the β‐diketone functionality is maintained. Five such derivatives have been prepared, and the X‐ray molecular structures for all of them have been determined. The tautomerism of the five compounds has been studied by NMR in the solid state and in solution. An enol–enol proton transfer barrier has been determined.