Anthocyanins and related compounds. Detecting the change of regime between rate control by hydration or by tautomerization

Dyes and Pigments

Volumn 102, Issue , 2014, Pages 308-314

  Pina, Fernando ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Anthocyanins; Flash photolysis; Flavylium; Photochromism; Stopped flow; Tautomerization

Indexed keywords

CHEMICAL TRANSFORMATIONS; EQUILIBRATED SOLUTIONS; FLASH PHOTOLYSIS; FLAVYLIUM; MATHEMATICAL EXPRESSIONS; RATE DETERMINING STEP; STOPPED FLOW; TAUTOMERIZATIONS;

ANTHOCYANINS; CHEMICAL REACTIONS; EQUILIBRIUM CONSTANTS; PH; PHOTOCHROMISM; POSITIVE IONS;

CHEMICAL COMPOUNDS;

EID: 84890096988     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.10.033     Document Type: Article

References (21)

1. L. Jurd Anthocyanidins and related compounds 15. Effects of sunlight on flavylium salt-chalcone equilibrium in acid solutions Tetrahedron 25 1969 2367 2380
2. P. Figueiredo, J.C. Lima, H. Santos, M.C. Wigand, R. Brouillard, and A.L. Maçanita Photochromism of the synthetic 4′,7-dihydroxyflavylium chloride J Am Chem Soc 116 1994 1249 1254
3. F. Pina, M.J. Melo, C.A.T. Laia, A.J. Parola, and J.C. Lima Chemistry and applications of flavylium compounds: a handful of colours Chem Soc Rev 41 2012 869 908
4. R.A. McClelland, and S. Gedge Hydration of the flavylium ion J Am Chem Soc 102 1980 5838 5848
5. R.A. McClelland, and G.H. McGall Hydration of the flavylium ion 2. The 4′-hydroxyflavylium ion J Org Chem 47 1982 3730 3736
6. R. Brouillard, and J.E. Dubois Mechanism of structural transformations of anthocyanins in acidic media J Am Chem Soc 99 1977 1359 1364
7. R. Brouillard, and B. Delaporte Chemistry of anthocyanin pigments 2. Kinetic and thermodynamic study of proton-transfer, hydration, and tautomeric reactions of malvidin 3-glucoside J Am Chem Soc 99 1977 8461 8468
8. R. Brouillard, and J. Lang The hemicetal-cis-chalcone-equilibrium of malvin, a natural anthocyanin Can J Chem 68 1990 755 761
9. C. Bülow, and H. Wagner Derivatives of 1.4-benzopyranol, the mother substance of a new class of pigments II. Ber 34 1901 1782 1804
10. A. Roque, C. Lodeiro, F. Pina, M. Maestri, S. Dumas, P. Passaniti, and V. Balzani Multistate/multifunctional systems. A thermodynamic, kinetic and photochemical investigation on the 4′-dimethylaminoflavylium compound J Am Chem Soc 125 2003 987 994 (Pubitemid 36152650)
11. F. Pina, M.J. Melo, M. Maestri, R. Ballardini, and V. Balzani Photochromism of 4′-methoxyflavylium perchorate. A "write-lock-read- unlock-erase" molecular switching device J Am Chem Soc 119 1997 5556 5561 (Pubitemid 27321414)
12. A.L. Maçanita, P. Moreira, J.C. Lima, F. Quina, C. Yihwa, and C. Vaultier-Giongo Proton transfer in anthocyanins and related flavylium salts. Determination of ground-state rate constants with nanosecond-laser flash photolysis (light pulse jump) J Phys Chem 2002 1248 1255 (Pubitemid 35264272)
13. F. Pina Thermodynamic and kinetics of flavylium salts. Malvin revisited J Chem Soc Faraday Trans 94 1998 2109 2121 Correction 1998; 94: 3781-81
14. V. Petrov, and F. Pina Analytical resolution of the reaction rates of flavylium network by Laplace transform J Math Chem 47 2010 1005 1026
15. H. Kuhn, and W. Sperling Experientia 16 1960 237 244
16. D. Dewar, and G. Sutherland J Chem Soc Chem Commun 1970 272 273
17. C.F. Timberlake, and P. Bridle Nature 212 1966 158 159
18. K.A. Harper, and B.V. Chandler Aust J Chem 20 1967 731 744
19. L. Jurd Chem Ind 1962 1197 1198
20. Y. Leydet, P. Batat, G. Jonusauskas, S. Denisov, J.C. Lima, and A.J. Parola Impact of water on the cis-trans photoisomerization of hydroxychalcones J Phys Chem 117 2013 4167 4173
21. F. Pina, M.J. Melo, R. Ballardini, L. Flamigni, and M. Maestri New J Chem 21 1997 969 976