(E)-2-Benzylidenebenzocyclanones, part VIII: Spectrophotometric determination of pK a values of some natural and synthetic chalcones and their cyclic analogues

Ivan Kron, Zuzana Pudychová-Chovanová, Beáta Veliká, Juraj Guzy, P. Perjési

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

UV-Vis spectrophotometry was used to determine acid dissociation constant (pKa) values of the natural flavonoids phloretin, phlorizin, naringenin, and naringin, as well as 4′-hydroxychalcone, 4′-(dimethylamino)chalcone, and their cyclic analogues. Comparison of the results with those previously reported for the natural flavonoids showed the applied method is a relatively straightforward and easy-to-perform technique for the determination of pK a values of compounds with relatively low solubility. Comparative analysis of the pK a values of the synthetic chalcones showed a strong correlation between the degree of conjugation and the acid strength of the respective compounds with different geometry. Our results provide further evidence that modification of the three-dimensional structure of open-chain bioactive compounds is the method of choice to modify not only their stereochemistry but also their physicochemical properties.

Original languageEnglish
Pages (from-to)13-17
Number of pages5
JournalMonatshefte fur Chemie
Volume143
Issue number1
DOIs
Publication statusPublished - Jan 2012

Fingerprint

Chalcones
Flavonoids
Phloretin
Phlorhizin
Stereochemistry
Acids
Spectrophotometry
Solubility
Geometry
dimethylaminochalcone
naringenin
naringin
4-hydroxychalcone

Keywords

  • Acidity
  • Chalcone derivatives
  • Structure-pK relationship
  • UV-Vis spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

(E)-2-Benzylidenebenzocyclanones, part VIII : Spectrophotometric determination of pK a values of some natural and synthetic chalcones and their cyclic analogues. / Kron, Ivan; Pudychová-Chovanová, Zuzana; Veliká, Beáta; Guzy, Juraj; Perjési, P.

In: Monatshefte fur Chemie, Vol. 143, No. 1, 01.2012, p. 13-17.

Research output: Contribution to journalArticle

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