Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins
A series of 1,3-bis-substituted-5,5-dimethylhydantoins was synthesized using the reaction of 5,5-dimethylhydantoin with the corresponding alkyl halide in the presence of trimethylamine as catalyst and sodium hydroxide, according to a modified literature procedure. The experimental investigation incl...
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doaj-4bef7a2e8fce409ba9f94ed40c9c1ae82020-12-24T12:11:51ZengSerbian Chemical Society Journal of the Serbian Chemical Society0352-51391820-74212003-01-01681069970610.2298/JSC0310699U0352-51390310699USynthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoinsUšćumlić Gordana S.0Kshad Abdulbaseta A.1Mijin Dušan Ž.2Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, P. O. Box 3503, 11120 Belgrade, Serbia and MontenegroDepartment of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, P. O. Box 3503, 11120 Belgrade, Serbia and MontenegroDepartment of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, P. O. Box 3503, 11120 Belgrade, Serbia and MontenegroA series of 1,3-bis-substituted-5,5-dimethylhydantoins was synthesized using the reaction of 5,5-dimethylhydantoin with the corresponding alkyl halide in the presence of trimethylamine as catalyst and sodium hydroxide, according to a modified literature procedure. The experimental investigation included modification of the synthetic procedure in terms of starting materials solvent, temperature, isolation techniques, as well as purification and identification of the products. The absorption spectra of the 1,3-bis-substituted-5,5-dimethylhydantoins were recorded in twelve solvents in the range 200–400 nm. The effects of the solvent polarity and hydrogen bonding on the absorption spectra were interpreted by means of linear solvation energy relationships using a general equation of the form ν = ν0 s¶* + aα + bβ and by two-parameter models presented by the equation ν = ν0 s¶* + aα, where ¶* is a measure of the solvent polarity/polarisability, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. The solvent and substituent effects on the electronic absorption spectra of the investigated hydantoins is discussed.http://www.doiserbia.nb.rs/img/doi/0352-5139/2003/0352-51390310699U.pdfultraviolet absorption spectrasolvent effectslinear salvation energy relationships1,3-bis-substituted-5,5-dimethylhydantoins |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ušćumlić Gordana S. Kshad Abdulbaseta A. Mijin Dušan Ž. |
spellingShingle |
Ušćumlić Gordana S. Kshad Abdulbaseta A. Mijin Dušan Ž. Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins Journal of the Serbian Chemical Society ultraviolet absorption spectra solvent effects linear salvation energy relationships 1,3-bis-substituted-5,5-dimethylhydantoins |
author_facet |
Ušćumlić Gordana S. Kshad Abdulbaseta A. Mijin Dušan Ž. |
author_sort |
Ušćumlić Gordana S. |
title |
Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
title_short |
Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
title_full |
Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
title_fullStr |
Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
title_full_unstemmed |
Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
title_sort |
synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1, 3-bis-substituted-5, 5-dimethylhydantoins |
publisher |
Serbian Chemical Society |
series |
Journal of the Serbian Chemical Society |
issn |
0352-5139 1820-7421 |
publishDate |
2003-01-01 |
description |
A series of 1,3-bis-substituted-5,5-dimethylhydantoins was synthesized using the reaction of 5,5-dimethylhydantoin with the corresponding alkyl halide in the presence of trimethylamine as catalyst and sodium hydroxide, according to a modified literature procedure. The experimental investigation included modification of the synthetic procedure in terms of starting materials solvent, temperature, isolation techniques, as well as purification and identification of the products. The absorption spectra of the 1,3-bis-substituted-5,5-dimethylhydantoins were recorded in twelve solvents in the range 200–400 nm. The effects of the solvent polarity and hydrogen bonding on the absorption spectra were interpreted by means of linear solvation energy relationships using a general equation of the form ν = ν0 s¶* + aα + bβ and by two-parameter models presented by the equation ν = ν0 s¶* + aα, where ¶* is a measure of the solvent polarity/polarisability, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. The solvent and substituent effects on the electronic absorption spectra of the investigated hydantoins is discussed. |
topic |
ultraviolet absorption spectra solvent effects linear salvation energy relationships 1,3-bis-substituted-5,5-dimethylhydantoins |
url |
http://www.doiserbia.nb.rs/img/doi/0352-5139/2003/0352-51390310699U.pdf |
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