Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones
Link to publisher's homepage at http://www.elsevier.com/
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
Elsevier B.V.
2013
|
| Subjects: | |
| Online Access: | http://dspace.unimap.edu.my/xmlui/handle/123456789/23362 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| id |
my.unimap-23362 |
|---|---|
| record_format |
dspace |
| spelling |
my.unimap-233622014-06-11T10:46:26Z Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones Wojciech, Kuznik Maximilian, N. Kopylovich Gunel, I. Amanullayeva Armando, J.L. Pombeiro Ali Hussain, Reshak, Prof. Dr. Kamran, T. Mahmudov Kityk, Iwan V pombeiro@ist.utl.pt maalidph@yahoo.co.uk iwank74@gmail.com Arylhydrazones of β-diketones Tautomeric equilibrium Solvatochromism Link to publisher's homepage at http://www.elsevier.com/ New arylhydrazones of β-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)hydrazinyl)-2-hydroxy- 5-nitrobenzenesulfonic acid (2), and 3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene) hydrazinyl)-2- hydroxy-5-nitrobenzenesulfonic acid (3), have been synthesized and characterized by IR, 1 H and 13 C 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. 2013-02-04T09:10:25Z 2013-02-04T09:10:25Z 2012-07 Article Journal of Molecular Liquids, vol. 171, 2012, pages 11–15 0167-7322 http://www.sciencedirect.com/science/article/pii/S0167732212001092 http://hdl.handle.net/123456789/23362 en Elsevier B.V. |
| institution |
Universiti Malaysia Perlis |
| building |
UniMAP Library |
| collection |
Institutional Repository |
| continent |
Asia |
| country |
Malaysia |
| content_provider |
Universiti Malaysia Perlis |
| content_source |
UniMAP Library Digital Repository |
| url_provider |
http://dspace.unimap.edu.my/ |
| language |
English |
| topic |
Arylhydrazones of β-diketones Tautomeric equilibrium Solvatochromism |
| spellingShingle |
Arylhydrazones of β-diketones Tautomeric equilibrium Solvatochromism Wojciech, Kuznik Maximilian, N. Kopylovich Gunel, I. Amanullayeva Armando, J.L. Pombeiro Ali Hussain, Reshak, Prof. Dr. Kamran, T. Mahmudov Kityk, Iwan V Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| description |
Link to publisher's homepage at http://www.elsevier.com/ |
| author2 |
pombeiro@ist.utl.pt |
| author_facet |
pombeiro@ist.utl.pt Wojciech, Kuznik Maximilian, N. Kopylovich Gunel, I. Amanullayeva Armando, J.L. Pombeiro Ali Hussain, Reshak, Prof. Dr. Kamran, T. Mahmudov Kityk, Iwan V |
| format |
Article |
| author |
Wojciech, Kuznik Maximilian, N. Kopylovich Gunel, I. Amanullayeva Armando, J.L. Pombeiro Ali Hussain, Reshak, Prof. Dr. Kamran, T. Mahmudov Kityk, Iwan V |
| author_sort |
Wojciech, Kuznik |
| title |
Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| title_short |
Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| title_full |
Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| title_fullStr |
Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| title_full_unstemmed |
Role of tautomerism and solvatochromism in UV–VIS spectra of arylhydrazones of β-diketones |
| title_sort |
role of tautomerism and solvatochromism in uv–vis spectra of arylhydrazones of β-diketones |
| publisher |
Elsevier B.V. |
| publishDate |
2013 |
| url |
http://dspace.unimap.edu.my/xmlui/handle/123456789/23362 |
| _version_ |
1643793973395849216 |
| score |
13.214268 |