Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones
Abstract
Spectral properties, solvatochromism and azo-hydrazone tautomerism of ten 5-(substituted phenylazo)3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones in twenty-two solvents are investigated. For quantitative evaluation of the solvent effects on the UV-vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalan. Linear free energy relationships are applied to the UV-vis absorption spectra and correlation of absorption frequencies with Hammett substituent constants are performed. Furthermore, the influence of the electronic nature of the substituents on H-1 and C-13 NMR shifts is investigated by simple and extended Hammett equations, as well as by Swain-Lupton equation.
Keywords:
solvatochromism / UV–vis absorption spectra / fluorescence spectra / Hammett EquationSource:
Chemical Physics Letters, 2014, 615, 62-68Publisher:
- Elsevier Science Bv, Amsterdam
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.cplett.2014.09.063
ISSN: 0009-2614
WoS: 000344747400012
Scopus: 2-s2.0-84949126947
Collections
Institution/Community
Institut za multidisciplinarna istraživanjaTY - JOUR AU - Mirković, Jelena M. AU - Bozic, Bojan D. AU - Mutavdžić, Dragosav AU - Uscumlic, Gordana S. AU - Mijin, Dušan PY - 2014 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/764 AB - Spectral properties, solvatochromism and azo-hydrazone tautomerism of ten 5-(substituted phenylazo)3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones in twenty-two solvents are investigated. For quantitative evaluation of the solvent effects on the UV-vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalan. Linear free energy relationships are applied to the UV-vis absorption spectra and correlation of absorption frequencies with Hammett substituent constants are performed. Furthermore, the influence of the electronic nature of the substituents on H-1 and C-13 NMR shifts is investigated by simple and extended Hammett equations, as well as by Swain-Lupton equation. PB - Elsevier Science Bv, Amsterdam T2 - Chemical Physics Letters T1 - Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones EP - 68 SP - 62 VL - 615 DO - 10.1016/j.cplett.2014.09.063 ER -
@article{ author = "Mirković, Jelena M. and Bozic, Bojan D. and Mutavdžić, Dragosav and Uscumlic, Gordana S. and Mijin, Dušan", year = "2014", abstract = "Spectral properties, solvatochromism and azo-hydrazone tautomerism of ten 5-(substituted phenylazo)3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones in twenty-two solvents are investigated. For quantitative evaluation of the solvent effects on the UV-vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalan. Linear free energy relationships are applied to the UV-vis absorption spectra and correlation of absorption frequencies with Hammett substituent constants are performed. Furthermore, the influence of the electronic nature of the substituents on H-1 and C-13 NMR shifts is investigated by simple and extended Hammett equations, as well as by Swain-Lupton equation.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Chemical Physics Letters", title = "Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones", pages = "68-62", volume = "615", doi = "10.1016/j.cplett.2014.09.063" }
Mirković, J. M., Bozic, B. D., Mutavdžić, D., Uscumlic, G. S.,& Mijin, D.. (2014). Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones. in Chemical Physics Letters Elsevier Science Bv, Amsterdam., 615, 62-68. https://doi.org/10.1016/j.cplett.2014.09.063
Mirković JM, Bozic BD, Mutavdžić D, Uscumlic GS, Mijin D. Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones. in Chemical Physics Letters. 2014;615:62-68. doi:10.1016/j.cplett.2014.09.063 .
Mirković, Jelena M., Bozic, Bojan D., Mutavdžić, Dragosav, Uscumlic, Gordana S., Mijin, Dušan, "Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones" in Chemical Physics Letters, 615 (2014):62-68, https://doi.org/10.1016/j.cplett.2014.09.063 . .