Journal
JOURNAL OF PHYSICAL CHEMISTRY B
Volume 114, Issue 41, Pages 13232-13240Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp1045673
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Funding
- FCT (Fundacao para a Ciencia e a Tecnologia) from Portugal [PTDC/QUI/67681/2006, CONC-REEQ/275/2001, SFRH/BD/30915/2006]
- [SFRH/BPD/18214/2004]
- Fundação para a Ciência e a Tecnologia [SFRH/BPD/18214/2004, PTDC/QUI/67681/2006, SFRH/BD/30915/2006] Funding Source: FCT
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The chemical equilibria of the pyranomalvidin-3-glucosides linked to (+)-catechin, (-)-epicatechin, and catechol moieties (and the respective coumaroylglucoside Compounds) were established by means of UV-vis spectroscopy. The conjugated double bonds among pyranic rings C and D provide a higher electronic delocalization that prevents the nucleophilic attack of water at position 2. Consequently, besides flavylium cation (AH(+)), the bases A, A(-), and A(2-) have been identified by increasing pH, and the respective acidity constants were determined by spectrophotometry. The formation of dimers at higher concentration was observed for pyranomalvidin-3-O-coumaroylglucoside-(+)-catechin, and the respective data treated by the exciton model suggests the for-nation of a chiller where the monomers form J-type aggregates with the dipolar moments in opposite directions and rotated by 174 degrees at a distance of 5.2 angstrom (from the center).
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