UV absorption and keto-enol tautomerism equilibrium of methoxy and dimethoxy 1,3-diphenylpropane-1,3-diones

Spectrochim Acta A Mol Biomol Spectrosc. 2010 Feb;75(2):925-9. doi: 10.1016/j.saa.2009.12.040. Epub 2009 Dec 16.

Abstract

UV absorption spectra of 1,3-diphenylpropane-1,3-dione (1), its three methoxy derivatives (2-4) and its six dimethoxy derivatives (5-10) in various solvents dissolved were collected. The keto-enol tautomerism equilibrium constant was calculated with (1)H NMR. The position of the methoxy group in 1,3-diphenylpropane-1,3-dione was shown to have an influence on the molecule's UV absorption spectrum and the keto-enol tautomerism equilibrium constant. The methoxy group in the para position increases the absorption of radiation in the UV-A range. A shift to the keto form in the keto-enol tautomerism equilibrium is experienced by compounds with methoxy groups in ortho position. When two methoxy groups are present, the influence of their position is cumulative.

MeSH terms

  • Chalcones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry, Ultraviolet*
  • Stereoisomerism

Substances

  • Chalcones