Computational insights into substituent effects on the stability and reactivity of flavylium cation analogs of anthocyanins

Autor(es)

Freitas, Adilson A. ; Shimizu, Karina ; Dias, Luis G. ; Quina, Frank H.

• Tipo de documento: Artigo Científico
• Fonte: ARKIVOC; v. N/A, p. 30-pg., 2020-01-01.

Resumo

Synthetic flavylium salts and natural anthocyanins undergo hydration by water at physiological pHs, fading out the color. Equilibrium constants of hydration (K-h), tautomerization (K-t) and isomerization (K-i) of 21 substituted flavylium salts were rationalized based on molecular properties calculated by density functional theory (DFT). The good correlations between core-electron binding energies and equilibrium constants revealed an intricate balance of the substitution pattern on the stabilization of AH(+) and neutral species, indicating that the apparent pK(ap) follows a non-linear relationship with Hammett substituent constants. [GRAPHICS] . (AU)

• Processo FAPESP: 17/03204-7 - Desenvolvimento e aplicação de campo de força coarse-graining em sistemas auto-organizados
• Beneficiário: Luis Gustavo Dias
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/08166-5 - Química em interfaces: interações de fármacos, peptídios e enzimas com membranas modelos
• Beneficiário: Iolanda Midea Cuccovia
• Modalidade de apoio: Auxílio à Pesquisa - Temático