5,6-Dihydroxyindole-2-carboxylic acid: a first principles density functional study

Title5,6-Dihydroxyindole-2-carboxylic acid: a first principles density functional study
Publication TypeJournal Article
Year of Publication2005
AuthorsPowell, Ben J.
JournalChemical Physics Letters
Volume402
Issue1-3
Pagination111–115
Date Publishedjan
AbstractWe report first principles density functional calculations for 5,6-dihydroxyindole-2-carboxylic acid (DHICA) and several oxidised forms. DHICA and 5,6-dihydroxyindole (DHI) are believed to be the basic building blocks of the eumelanins. Our results show that carboxylation has a significant effect on the physical properties of the molecules. In particular, the relative stabilities and the highest occupied molecular orbital-lowest unoccupied molecular orbital gaps (calculated with the DeltaSCF method) of the various redox forms are strongly affected. We predict that, in contrast to DHI, the density of unpaired electrons, and hence the ESR signal, in DHICA is negligibly small. (C) 2004 Elsevier B.V. All rights reserved.