About: Role of tautomerism and solvatochromism in UV-VIS spectra of arylhydrazones of beta-diketones

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	New arylhydrazones of beta-diketones, 5-chloro-3-(2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyl)-2-hydroxybenzenesulfonic acid (1), 3-(2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyI)-2-hydroxy-5-nitrobenzenesulfonic acid (2), and 3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene) hydrazinyI)-2-hydroxy-5-nitrobenzenesulfonic acid (3), have been synthesized and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. 3 and known 5-(2-(4.4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-4-hydroxybenzene-1,3-disulfonic acid (4) exist in DMSO solution exclusively in the hydrazone form, while 1 and 2 exist in DMSO and H2O solutions as a mixture of enol-azo and hydrazone tautomeric forms, in ratios dependent on the solvent polarity and inductive effect of the substituents. DFT and TDDFT approaches were applied for simulations of experimental UV-VIS absorption spectra of the studied compounds, taking into account solvatochromic as well as tautomeric effect. The performed simulations have established a correlation of substantial experimental 120 nm red shift of the enol-azo form with respect to hydrazone with HOMO and LUMO orbitals' delocalization. Crown New arylhydrazones of beta-diketones, 5-chloro-3-(2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyl)-2-hydroxybenzenesulfonic acid (1), 3-(2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyI)-2-hydroxy-5-nitrobenzenesulfonic acid (2), and 3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene) hydrazinyI)-2-hydroxy-5-nitrobenzenesulfonic acid (3), have been synthesized and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. 3 and known 5-(2-(4.4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-4-hydroxybenzene-1,3-disulfonic acid (4) exist in DMSO solution exclusively in the hydrazone form, while 1 and 2 exist in DMSO and H2O solutions as a mixture of enol-azo and hydrazone tautomeric forms, in ratios dependent on the solvent polarity and inductive effect of the substituents. DFT and TDDFT approaches were applied for simulations of experimental UV-VIS absorption spectra of the studied compounds, taking into account solvatochromic as well as tautomeric effect. The performed simulations have established a correlation of substantial experimental 120 nm red shift of the enol-azo form with respect to hydrazone with HOMO and LUMO orbitals' delocalization. Crown (en)
Title	Role of tautomerism and solvatochromism in UV-VIS spectra of arylhydrazones of beta-diketones Role of tautomerism and solvatochromism in UV-VIS spectra of arylhydrazones of beta-diketones (en)
skos:prefLabel	Role of tautomerism and solvatochromism in UV-VIS spectra of arylhydrazones of beta-diketones Role of tautomerism and solvatochromism in UV-VIS spectra of arylhydrazones of beta-diketones (en)
skos:notation	RIV/60076658:12520/12:43884003!RIV13-MSM-12520___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ED2.1.00/01.0024)
http://linked.open...iv/cisloPeriodika	05
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Reshak, Ali Hussain
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Jihočeská univerzita v Českých Budějovicích / Fakulta rybářství a ochrany vod
http://linked.open...dnocenehoVysledku	166067
http://linked.open...ai/riv/idVysledku	RIV/60076658:12520/12:43884003
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Solvatochromism; Tautomeric equilibrium; Arylhydrazones of beta-diketones; ION; RESONANCE; CONVERSION; HYDROGEN-BOND (en)
http://linked.open.../riv/klicoveSlovo	HYDROGEN-BOND ION Solvatochromism Arylhydrazones of beta-diketones CONVERSION RESONANCE Tautomeric equilibrium
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[01758BB55B69]
http://linked.open...i/riv/nazevZdroje	JOURNAL OF MOLECULAR LIQUIDS
http://linked.open...in/vavai/riv/obor	BH
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...vavai/riv/projekt	South Bohemian Research Center of Aquaculture and Biodiversity of Hydrocenoses
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	171
http://linked.open...iv/tvurceVysledku	Reshak, Ali Hussain Kityk, I. V. Amanullayeva, Gunel I. Kopylovich, Maximilian N. Kuznik, Wojciech Mahmudov, Kamran T. Pombeiro, Armando J. L.
http://linked.open...ain/vavai/riv/wos	000306250200003
issn	0167-7322
number of pages	5 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molliq.2012.03.023
http://localhost/t...ganizacniJednotka	12520

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