Document Type

Conference Proceeding

Publication Date

Spring 2015

Publication Title

American Chemical Society National Meeting

Abstract

Curcumin, the primary natural dye from the spice turmeric, has been of recent interest due to its possible health benefits as an antioxidant and possible anti cancer and anti Alzheimer's properties. Limited solubility and instability in water are of primary importance when considering curcumin's possible uses as a pharmaceutical. DFT computations were carried out using B3LYP and MO6 density functionals and the SMD solvent model for water. TDDFT computations were carried out on geometries optimized in water as described by the SMD solvent model. It is found that M06 with the 3-21G* basis set and SMD solvent model gives accurate λmax values though the larger 6-31+G* basis set is needed for accurate description of the trianionic protonation state. The 6-31+G* basis set is also needed for accurate computation of pKa values. The particle-in-a-box model gives unexpectedly good agreement with computational λmax values when delocalization of phenolic lone pair electrons are appropriately considered in the different protonation states and box lengths from optimized geometries are used. This gives a simple model of how the electronic structure of curcumin is influenced by protonation state and is in good agreement with both computation and experiment.

Comments

This oral presentation was presented at the 2015 Spring American Chemical Society National Meeting.

Primo Type

Conference Proceeding

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