Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones
Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona
2010
Аутори
Alimmari, Adel SAMarinković, Aleksandar D.
Mijin, Dušan
Valentić, Nataša V.
Todorović, Nina
Ušćumlić, Gordana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.
Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača.
Кључне речи:
arylazo pyridone dyes / absorption spectra / solvent effect / substituent effect / tautomeric equilibrationИзвор:
Journal of the Serbian Chemical Society, 2010, 75, 8, 1019-1032Издавач:
- Serbian Chemical Society
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-MPN2006-2010-142063)
DOI: 10.2298/JSC091009074A
ISSN: 0352-5139
WoS: 000281683900001
Scopus: 2-s2.0-77956426927
Институција/група
IHTMTY - JOUR AU - Alimmari, Adel SA AU - Marinković, Aleksandar D. AU - Mijin, Dušan AU - Valentić, Nataša V. AU - Todorović, Nina AU - Ušćumlić, Gordana PY - 2010 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/712 AB - A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents. AB - Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones T1 - Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona VL - 75 IS - 8 SP - 1019 EP - 1032 DO - 10.2298/JSC091009074A ER -
@article{ author = "Alimmari, Adel SA and Marinković, Aleksandar D. and Mijin, Dušan and Valentić, Nataša V. and Todorović, Nina and Ušćumlić, Gordana", year = "2010", abstract = "A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents., Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones, Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona", volume = "75", number = "8", pages = "1019-1032", doi = "10.2298/JSC091009074A" }
Alimmari, A. S., Marinković, A. D., Mijin, D., Valentić, N. V., Todorović, N.,& Ušćumlić, G.. (2010). Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones. in Journal of the Serbian Chemical Society Serbian Chemical Society., 75(8), 1019-1032. https://doi.org/10.2298/JSC091009074A
Alimmari AS, Marinković AD, Mijin D, Valentić NV, Todorović N, Ušćumlić G. Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones. in Journal of the Serbian Chemical Society. 2010;75(8):1019-1032. doi:10.2298/JSC091009074A .
Alimmari, Adel SA, Marinković, Aleksandar D., Mijin, Dušan, Valentić, Nataša V., Todorović, Nina, Ušćumlić, Gordana, "Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones" in Journal of the Serbian Chemical Society, 75, no. 8 (2010):1019-1032, https://doi.org/10.2298/JSC091009074A . .