Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline

Güp, Ramazan; Giziroglu, Emrah; Kırkan, Bülent

doi:10.1016/j.dyepig.2005.10.005

Cited by 120 publications

(58 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Based on the stretching frequency, this analysis indicates that the binding mode of thiocyanate is N-bonded; this is similar to what has been observed in the literature [33][34][35] . Further confirmation resides in the absorption band at 846-855 cm −1 , which is attributed to the ν(CS) stretching frequency of Nbonded ligands 31,32 ; and in the weak intensity band around 434-476 cm −1 , interpreted as the M−N stretching frequency.…”

Section: Infrared (Ir) Studiesmentioning

confidence: 86%

“…This evidence confirmed the coordination of the Clazpy ligand to the metal centres as well as the function of the azo group to stabilize the lower oxidation state of the metal centres 11 . In addition, the strong sharp band around 2074-2092 cm −1 corresponds to the ν(NCS) thiocyanate stretching frequency [29][30][31][32] . In this case, it has been indicated that the ν as (C − − − N) frequencies could be used as a criterion to differentiate between S-bonded (2110-2140 cm −1 ) and N-bonded (< 2110 cm −1 ) complexes 33,34 .…”

Section: Infrared (Ir) Studiesmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Vittaya¹,

Leesakul²,

Saithong³

et al. 2017

ScienceAsia

View full text Add to dashboard Cite

An azoimine compound, 5-chloro-2-(phenylazo)pyridine (Clazpy), reacted with Ni(II) and Zn(II) sulphate salts and formed divalent metal complexes with a general formula of [M(Clazpy) 2 (NCS) 2 ], where M is Ni(II) or Zn(II). The synthesized complexes were characterized on the basis of elemental analysis, nuclear magnetic resonance, and infrared and electronic absorption spectroscopy. The single crystal X-ray diffraction and infrared data of the Zn(II) complex show that the ligand coordinates through the donating nitrogen atoms of the pyridine ring and azo moiety of Clazpy and N atoms of the thiocyanate groups. Our density functional theory calculations used the B3LYP/6-31G(d,p)&LANL2DZ functional and basis sets to predict the most favourable structures of [Ni(Clazpy) 2 (NCS) 2 ] and [Zn(Clazpy) 2 (NCS) 2 ]. The TD-CAM-B3LYP/6-31+G(d,p)&LANL2DZ electronic transition energies agree with the electronic spectra and hence confirm their structures. Minimal inhibitory concentrations (MIC) and minimal bactericidal concentrations or minimal fungicidal concentrations (MFC) of all tested compounds were determined against human pathogens by a colorimetric microdilution method. The Clazpy compound and its complexes are significantly active against yeast and filamentous fungus with MIC and MFC values of 32 and 200 µg/ml, respectively. The Clazpy ligand showed higher antimicrobial activities against pathogenic yeast Cryptococcus neoformans (MIC/MFC 32/32 µg/ml) than both complexes (MIC/MFC 64/128 µg/ml). The [Ni(Clazpy) 2 (NCS) 2 ] complex exhibited higher antimicrobial activities against fungal strains of Microsporum gypseum (MIC/MFC 64/128 µg/ml) than the [Zn(Clazpy) 2 (NCS) 2 ] complex. These new azoimine metal complexes might therefore be considered as prospective antifungal agents.

show abstract

Section: Infrared (Ir) Studiesmentioning

confidence: 86%

Section: Infrared (Ir) Studiesmentioning

confidence: 99%

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Vittaya¹,

Leesakul²,

Saithong³

et al. 2017

ScienceAsia

View full text Add to dashboard Cite

show abstract

“…[8 -19] The slow exchange of amide hydrogens has led to the observation of isotopic multiplets in the spectra of amides. [8,10,11] The tautomeric forms of azo dyes based on barbituric acid have been assigned by IR, [20] 1 H NMR, [21] and UV-visible [22] spectroscopy. However, the isotope multiplicity of carbon-13 not only assigns carbon atoms in structure backbone, but also assigns tautomeric forms by proton/deuterium exchange, as is described in this work.…”

Section: Introductionmentioning

confidence: 99%

Tautomeric behaviour and isotopic multiplets in the ¹³C NMR spectra of partially deuterated 5‐arylazo‐pyrimidine (1H,3H,5H)‐2,4,6‐triones and 5‐arylazo‐2‐thioxo‐pyrimidine (1H,3H,5H)‐4,6‐diones—evidence for elucidation of tautomeric forms

Pesyan

2009

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

NMR spectra of the synthesized azo dyes, 5-arylazo-pyrimidine (1H,3H,5H)-2,4,6-triones (5a-g), 1,3-dimethyl-5-arylazo-pyrimidine (1H,3H,5H)-2,4,6-triones (6a-g), and 5-arylazo-2-thioxo-pyrimidine (1H,3H,5H)-4,6-diones (7a-g) were studied in (CD(3))(2)SO (three drops of CD(3)OD were added into solutions of the dyes in two different concentrations). All dyes showed intramolecular hydrogen bonding. Dyes 5a-7a showed bifurcated intramolecular hydrogen bonds. Tautomeric behaviours of some of N-methylated azo dyes (6a-g) were studied in two different concentrations. The solvent-substrate proton exchange of dyes 5a-d, 6a and 7a-e was examined in presence of three drops of CD(3)OD. The dyes which were soluble in (CD(3))(2)SO containing CD(3)OD showed isotopic splitting (beta-isotope effect) in the (13)C NMR spectra.

show abstract

“…Azo compounds are highly colored and have been used as dyes and pigments for a long time. They have also been used in many practical applications such as coloring fibers, photoelectronic applications, and analytical chemistry (Koh and Greaves 2001;Hallas and Choi 1999;Gup et al 2007). …”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation

et al. 2008

View full text Add to dashboard Cite

N,N′-Pyromelliticdiimido-di-L-amino acids (1a-1d) were prepared from the reaction of pyromellitic dianhydride with the corresponding L-amino acids in a solution of glacial acetic acid/ pyridine (3:2) at refluxing temperature. 4,4′-sulfonyl bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, 4,4′-oxy bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol and 4,4′-methylene bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, were prepared from 4,4′-diamino diphenyl sulfone, 4,4′-diamino diphenyl ether, 4,4′-diamino diphenyl methane, sodium nitrite and phenol following the general procedure of diazo coupling. Interfacial polycondensation method was used to prepare the corresponding poly(azo-ester-imid)s (PAEI 1-12 ) in biphasic solution of water/ dichloromethane. The resulting polymers (PAEIs) have been obtained in high yields having good inherent viscosities (0.32-0.57 dl g −1 ), optical activities and thermal stabilities.

show abstract

Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline

Cited by 120 publications

References 25 publications

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Tautomeric behaviour and isotopic multiplets in the ¹³C NMR spectra of partially deuterated 5‐arylazo‐pyrimidine (1H,3H,5H)‐2,4,6‐triones and 5‐arylazo‐2‐thioxo‐pyrimidine (1H,3H,5H)‐4,6‐diones—evidence for elucidation of tautomeric forms

Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation

Contact Info

Product

Resources

About

Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline

Cited by 120 publications

References 25 publications

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Synthesis, characterization, and biological studies of novel Ni(II) and Zn(II) complexes with 5-chloro-2-(phenylazo)pyridine

Tautomeric behaviour and isotopic multiplets in the 13C NMR spectra of partially deuterated 5‐arylazo‐pyrimidine (1H,3H,5H)‐2,4,6‐triones and 5‐arylazo‐2‐thioxo‐pyrimidine (1H,3H,5H)‐4,6‐diones—evidence for elucidation of tautomeric forms

Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation

Contact Info

Product

Resources

About

Tautomeric behaviour and isotopic multiplets in the ¹³C NMR spectra of partially deuterated 5‐arylazo‐pyrimidine (1H,3H,5H)‐2,4,6‐triones and 5‐arylazo‐2‐thioxo‐pyrimidine (1H,3H,5H)‐4,6‐diones—evidence for elucidation of tautomeric forms