Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II
Efekat supstituenata na apsorpcione spektre 3-N-(4-supstituisanih fenil)-5-karboksi uracila u različitim rastvaračima - deo II
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Absorption spectra of some 3-N-(4-substituted phenyl)-5-carboxy uracils, previously determined in twelve solvents, are correlated with substituent sp+ values or by dual substituent parameter correlations involving sI and sR+ values. The substituents at the phenyl nucleus are as follows: H, Cl, Br, I, Me, Et, OMe, COOH and NO2. Considering the structure of the investigated system, it is very probable that the effect of the substituent at the phenyl nucleus on the electronic spectra of the substituted uracils is influenced by resonance interactions between the electron pairs of both the nitrogen atoms, the carbonyl groups and the substituent itself. The polarity of the reaction medium also affects the complex resonance interactions in the molecules of the investigated compounds. The obtained results support a suggestion made by Brownlee and Topsom that UV/visible spectral shifts can conform to reasonable precise linear free energy relationships if the substituent is not a part of the chr...omophoric system.
Apsorpcioni spektri 3-N-(4-supstituisanih fenil)-5-karboksi uracila (supstiuenti: H, Cl, Br, I, Me, Et, OMe, COOH i NO2) su korelisani prostom i proširenom Hammett-ovom jednačinom uključujući sp+ odnosno sI i sR+ konstante u dvanaest rastvarača različite polarnosti. Zadovoljavajući rezultati korelacije apsorbcionih spektara za elektronske prelaze u karboksi karbonilnoj grupi sa konstantama supstiuenata su potvrda ispravnosti odabranog modela za proučavanje mehanizma prenošenja efekata supstituenata kroz složene molekule 3-N-(4-supstituisanih fenil)-5-karboksi uracila.
Кључне речи:
absorption spectra / substituent effects / solvent effects / intramolecular hydrogen bondИзвор:
Journal of the Serbian Chemical Society, 2000, 65, 2, 81-86Издавач:
- Serbian Chemical Society, Belgrade
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Valentić, Nataša AU - Ušćumlić, Gordana AU - Radojković-Veličković, M. PY - 2000 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/288 AB - Absorption spectra of some 3-N-(4-substituted phenyl)-5-carboxy uracils, previously determined in twelve solvents, are correlated with substituent sp+ values or by dual substituent parameter correlations involving sI and sR+ values. The substituents at the phenyl nucleus are as follows: H, Cl, Br, I, Me, Et, OMe, COOH and NO2. Considering the structure of the investigated system, it is very probable that the effect of the substituent at the phenyl nucleus on the electronic spectra of the substituted uracils is influenced by resonance interactions between the electron pairs of both the nitrogen atoms, the carbonyl groups and the substituent itself. The polarity of the reaction medium also affects the complex resonance interactions in the molecules of the investigated compounds. The obtained results support a suggestion made by Brownlee and Topsom that UV/visible spectral shifts can conform to reasonable precise linear free energy relationships if the substituent is not a part of the chromophoric system. AB - Apsorpcioni spektri 3-N-(4-supstituisanih fenil)-5-karboksi uracila (supstiuenti: H, Cl, Br, I, Me, Et, OMe, COOH i NO2) su korelisani prostom i proširenom Hammett-ovom jednačinom uključujući sp+ odnosno sI i sR+ konstante u dvanaest rastvarača različite polarnosti. Zadovoljavajući rezultati korelacije apsorbcionih spektara za elektronske prelaze u karboksi karbonilnoj grupi sa konstantama supstiuenata su potvrda ispravnosti odabranog modela za proučavanje mehanizma prenošenja efekata supstituenata kroz složene molekule 3-N-(4-supstituisanih fenil)-5-karboksi uracila. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II T1 - Efekat supstituenata na apsorpcione spektre 3-N-(4-supstituisanih fenil)-5-karboksi uracila u različitim rastvaračima - deo II EP - 86 IS - 2 SP - 81 VL - 65 UR - https://hdl.handle.net/21.15107/rcub_technorep_288 ER -
@article{ author = "Valentić, Nataša and Ušćumlić, Gordana and Radojković-Veličković, M.", year = "2000", abstract = "Absorption spectra of some 3-N-(4-substituted phenyl)-5-carboxy uracils, previously determined in twelve solvents, are correlated with substituent sp+ values or by dual substituent parameter correlations involving sI and sR+ values. The substituents at the phenyl nucleus are as follows: H, Cl, Br, I, Me, Et, OMe, COOH and NO2. Considering the structure of the investigated system, it is very probable that the effect of the substituent at the phenyl nucleus on the electronic spectra of the substituted uracils is influenced by resonance interactions between the electron pairs of both the nitrogen atoms, the carbonyl groups and the substituent itself. The polarity of the reaction medium also affects the complex resonance interactions in the molecules of the investigated compounds. The obtained results support a suggestion made by Brownlee and Topsom that UV/visible spectral shifts can conform to reasonable precise linear free energy relationships if the substituent is not a part of the chromophoric system., Apsorpcioni spektri 3-N-(4-supstituisanih fenil)-5-karboksi uracila (supstiuenti: H, Cl, Br, I, Me, Et, OMe, COOH i NO2) su korelisani prostom i proširenom Hammett-ovom jednačinom uključujući sp+ odnosno sI i sR+ konstante u dvanaest rastvarača različite polarnosti. Zadovoljavajući rezultati korelacije apsorbcionih spektara za elektronske prelaze u karboksi karbonilnoj grupi sa konstantama supstiuenata su potvrda ispravnosti odabranog modela za proučavanje mehanizma prenošenja efekata supstituenata kroz složene molekule 3-N-(4-supstituisanih fenil)-5-karboksi uracila.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II, Efekat supstituenata na apsorpcione spektre 3-N-(4-supstituisanih fenil)-5-karboksi uracila u različitim rastvaračima - deo II", pages = "86-81", number = "2", volume = "65", url = "https://hdl.handle.net/21.15107/rcub_technorep_288" }
Valentić, N., Ušćumlić, G.,& Radojković-Veličković, M.. (2000). Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 65(2), 81-86. https://hdl.handle.net/21.15107/rcub_technorep_288
Valentić N, Ušćumlić G, Radojković-Veličković M. Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II. in Journal of the Serbian Chemical Society. 2000;65(2):81-86. https://hdl.handle.net/21.15107/rcub_technorep_288 .
Valentić, Nataša, Ušćumlić, Gordana, Radojković-Veličković, M., "Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents: Part II" in Journal of the Serbian Chemical Society, 65, no. 2 (2000):81-86, https://hdl.handle.net/21.15107/rcub_technorep_288 .