Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones
Solvatohromizam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona
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Eight 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones were synthesized by reaction of benzoylacetone and arendiazonium salt, followed by condensation with cyanoacetamide. Absorption spectra of all azo pyridone dyes were recorded in twelve protic and aprotic solvents in the range of 200-600 nm. A simple Hammett equation was used to study the effect of the substituents on the absorption spectra of these azo dyes. The solute-solvent interactions were clarified on the basis of linear solvation energy relationships concept proposed by Kamlet and Taft. The results showed that the solvent effects on the absorption spectra of the investigated azo dyes were very complex and strongly dependent on the nature of the substituents on the phenylazo group.
Osam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona je sintetizovano reakcijom benzoilacetona i arendiazonijumove soli, i kondenzacijom nastalog proizvoda sa cijano-acetamidom. Apsorpcioni spektri dobijenih arilazo piridonskih boja su snimljeni u dvanaest protičnih i aprotičnih rastvarača u opsegu od 200-600 nm. Za proučavanje uticaja supstituenata na apsorpcione spektre ispitivanih azo boja korišćena je prosta ametova jednačina. Interakcije rastvorak-rastvarač su razjašnjene na osnovu koncepta linearne korelacije energije solvatacije, koji su predložili Kamlet i Taft. Rezultati pokazuju da su efekti rastvarača na apsorpcione spektre istraženih azo boja veoma kompleksni i jako zavise od prirode supstituenata na fenilazo grupi.
Кључне речи:
Arylazo pyridone dyes / solvent effects / substituent effects / absorption spectra / arilazo piridonske boje / uticaj rastvarača / uticaj supstituenata / apsorpcioni spektriИзвор:
Zaštita materijala, 2018, 59, 1, 117-125Издавач:
- Engineering Society for Corrosion, Belgrade, Serbia
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Valentić, Nataša AU - Lađarević, Jelena AU - Božić, Bojan AU - Mijin, Dušan AU - Ušćumlić, Gordana PY - 2018 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3834 AB - Eight 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones were synthesized by reaction of benzoylacetone and arendiazonium salt, followed by condensation with cyanoacetamide. Absorption spectra of all azo pyridone dyes were recorded in twelve protic and aprotic solvents in the range of 200-600 nm. A simple Hammett equation was used to study the effect of the substituents on the absorption spectra of these azo dyes. The solute-solvent interactions were clarified on the basis of linear solvation energy relationships concept proposed by Kamlet and Taft. The results showed that the solvent effects on the absorption spectra of the investigated azo dyes were very complex and strongly dependent on the nature of the substituents on the phenylazo group. AB - Osam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona je sintetizovano reakcijom benzoilacetona i arendiazonijumove soli, i kondenzacijom nastalog proizvoda sa cijano-acetamidom. Apsorpcioni spektri dobijenih arilazo piridonskih boja su snimljeni u dvanaest protičnih i aprotičnih rastvarača u opsegu od 200-600 nm. Za proučavanje uticaja supstituenata na apsorpcione spektre ispitivanih azo boja korišćena je prosta ametova jednačina. Interakcije rastvorak-rastvarač su razjašnjene na osnovu koncepta linearne korelacije energije solvatacije, koji su predložili Kamlet i Taft. Rezultati pokazuju da su efekti rastvarača na apsorpcione spektre istraženih azo boja veoma kompleksni i jako zavise od prirode supstituenata na fenilazo grupi. PB - Engineering Society for Corrosion, Belgrade, Serbia T2 - Zaštita materijala T1 - Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones T1 - Solvatohromizam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona EP - 125 IS - 1 SP - 117 VL - 59 DO - 10.5937/ZasMat1801119V ER -
@article{ author = "Valentić, Nataša and Lađarević, Jelena and Božić, Bojan and Mijin, Dušan and Ušćumlić, Gordana", year = "2018", abstract = "Eight 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones were synthesized by reaction of benzoylacetone and arendiazonium salt, followed by condensation with cyanoacetamide. Absorption spectra of all azo pyridone dyes were recorded in twelve protic and aprotic solvents in the range of 200-600 nm. A simple Hammett equation was used to study the effect of the substituents on the absorption spectra of these azo dyes. The solute-solvent interactions were clarified on the basis of linear solvation energy relationships concept proposed by Kamlet and Taft. The results showed that the solvent effects on the absorption spectra of the investigated azo dyes were very complex and strongly dependent on the nature of the substituents on the phenylazo group., Osam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona je sintetizovano reakcijom benzoilacetona i arendiazonijumove soli, i kondenzacijom nastalog proizvoda sa cijano-acetamidom. Apsorpcioni spektri dobijenih arilazo piridonskih boja su snimljeni u dvanaest protičnih i aprotičnih rastvarača u opsegu od 200-600 nm. Za proučavanje uticaja supstituenata na apsorpcione spektre ispitivanih azo boja korišćena je prosta ametova jednačina. Interakcije rastvorak-rastvarač su razjašnjene na osnovu koncepta linearne korelacije energije solvatacije, koji su predložili Kamlet i Taft. Rezultati pokazuju da su efekti rastvarača na apsorpcione spektre istraženih azo boja veoma kompleksni i jako zavise od prirode supstituenata na fenilazo grupi.", publisher = "Engineering Society for Corrosion, Belgrade, Serbia", journal = "Zaštita materijala", title = "Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones, Solvatohromizam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona", pages = "125-117", number = "1", volume = "59", doi = "10.5937/ZasMat1801119V" }
Valentić, N., Lađarević, J., Božić, B., Mijin, D.,& Ušćumlić, G.. (2018). Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones. in Zaštita materijala Engineering Society for Corrosion, Belgrade, Serbia., 59(1), 117-125. https://doi.org/10.5937/ZasMat1801119V
Valentić N, Lađarević J, Božić B, Mijin D, Ušćumlić G. Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones. in Zaštita materijala. 2018;59(1):117-125. doi:10.5937/ZasMat1801119V .
Valentić, Nataša, Lađarević, Jelena, Božić, Bojan, Mijin, Dušan, Ušćumlić, Gordana, "Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones" in Zaštita materijala, 59, no. 1 (2018):117-125, https://doi.org/10.5937/ZasMat1801119V . .