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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

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2010
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Autori
Alimmari, Adel SA
Marinković, Aleksandar D.
Mijin, Dušan
Valentić, Nataša V.
Todorović, Nina
Ušćumlić, Gordana
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
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.
Ključne reči:
arylazo pyridone dyes / absorption spectra / solvent effect / substituent effect / tautomeric equilibration
Izvor:
Journal of the Serbian Chemical Society, 2010, 75, 8, 1019-1032
Izdavač:
  • Serbian Chemical Society
Projekti:
  • Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)

DOI: 10.2298/JSC091009074A

ISSN: 0352-5139

WoS: 000281683900001

Scopus: 2-s2.0-77956426927
[ Google Scholar ]
9
8
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/712
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija
IHTM
TY  - 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  - http://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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/712",
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 AS, Marinković AD, Mijin D, Valentić NV, Todorović N, Ušćumlić G. Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona. Journal of the Serbian Chemical Society. 2010;75(8):1019-1032
Alimmari, A. S., Marinković, A. D., Mijin, D., Valentić, N. V., Todorović, N.,& Ušćumlić, G. (2010). Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona.
Journal of the Serbian Chemical SocietySerbian Chemical Society., 75(8), 1019-1032.
https://doi.org/10.2298/JSC091009074A
Alimmari Adel SA, Marinković Aleksandar D., Mijin Dušan, Valentić Nataša V., Todorović Nina, Ušćumlić Gordana, "Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona" 75, no. 8 (2010):1019-1032,
https://doi.org/10.2298/JSC091009074A .

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