Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Akçay, Hakkı Türker; Bayrak, Rıza; Karslıoğlu, Selami; Şahin, Ertan

doi:10.1016/j.jorganchem.2012.03.016

Cited by 26 publications

(9 citation statements)

References 61 publications

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“…In our study, the vibrations observed at 1486-1079 cm -1 are calculated to occur at 1480-1104 cm -1 and are characterized as C-H bending vibrations in plane. All these results are in good agreement with the associated literature [30,31,33,34].…”

Section: Theoretical and Experimental Molecular Structure Parameterssupporting

confidence: 93%

“…In this study, the peaks calculated to be at 1104, 1085, 1010, 902, 837, 762, 712, and 687 cm -1 are matched with the peaks observed at 1079, 1056, 991, 901, 853, 772, 719, and 693 cm -1 and defined as wagging [30,35,36]. CCC (in-plane bending) vibration is observed at about 1000 cm -1 .…”

Section: Theoretical and Experimental Molecular Structure Parameterssupporting

confidence: 76%

“…The theoretical C≡N stretching vibrations were calculated to be at 2265 and 2269 cm -1 and were observed at 2231 cm -1 . The reason why only one sharp peak was observed in the theoretical and experimental spectra may be due to two C≡N stretching vibrations that are very near to each other [30][31][32].…”

Section: Theoretical and Experimental Molecular Structure Parametersmentioning

confidence: 98%

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Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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In this study, 4-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile was synthesized and its molecular structure was characterized by means of FT-IR and X-ray diffraction methods. The crystal is monoclinic and belongs to the P21/n space group. There are three weak intermolecular C-H…N type hydrogen bonds in the molecular structure. The geometrical parameters, vibration frequencies, HOMO-LUMO energies, and molecular electrostatic potential (MEP) map of the compound (3) in ground state were calculated by using density functional theory (DFT/B3LYP) with the 6-311G(d) basis set. Calculated geometrical parameters were compared with X-ray diffraction geometric parameters. On the other hand, theoretical and experimental FT-IR results were also compared.Keywords: crystal structure; 1,2,4-triazole; DFT calculations; molecular electrostatic potential; frontier orbitals ЕКСПЕРИМЕНТАЛНИ И ТЕОРЕТСКИ ИСПИТУВАЊА НА 4-[(4-МЕТИЛ-5-ФЕНИЛ-4H1,2,4-ТРИАЗОЛ-3-ИЛ)СУЛФАНИЛ]БЕНЗЕН-1,2-ДИКАРБОНИТРИЛВо ова истражување беше синтетизиран 4-[(4-метил-5-фенил-4Н1,2,4-триазол-3-ил)сул-фанил]бензен-1,2-дикарбонитрил, а неговата структура беше карактеризирана со помош на FT-IR и рендгенска дифракција. Кристалот е моноклиничен и припаѓа на просторната група P21/n. Во молекулската структура постојат три слаби интермолекулски водородни врски од типот на C-H…N. Геометриските параметри, вибрациските фреквенции, енергиите на HOMO-LUMO и мапата на молекулскиот електростатички потенцијал (MEP) на соединението (3) во основна состојба беа пресметани со теоријата на функционалот на густината (DFT/B3LYP) и основен сет 6-311G(d). Пресметаните геометриски параметри беа споредени со геометриските параметри добиени со рендгенската дифракција. Исто така беа споредени и теоретските и експерименталните резултати добиени со FT-IR.Клучни зборови: кристална структура; 1,2,4-триазол; DFT пресметки; молекулски електростатички потенцијал; гранични орбитали U. Çoruh, R. Ustabaş, H. T. Akçay, E. Menteşe, E. M. V. Lopez Maced.

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Section: Theoretical and Experimental Molecular Structure Parameterssupporting

confidence: 93%

Section: Theoretical and Experimental Molecular Structure Parameterssupporting

confidence: 76%

Section: Theoretical and Experimental Molecular Structure Parametersmentioning

confidence: 98%

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Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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“…Imidazole-substituted phthalocyanines can also be utilized in photodynamic therapy [156], electron transfer process [157], and the synthesis of polymeric phthalocyanines [158]. A new type of metal-free phthalocyanine and the respective Zn-, Ni-, Co-and Cu-complexes with peripheral tetra-imidazole substituents were introduced in 2012 [159]. A phthalonitrile derivative 170 was prepared in fair yields from the reaction between 168 and 4-nitrophthalonitrile 169 in dry DMF in the presence of anhydrous K 2 CO 3 to yield basic reaction conditions.…”

Section: Synthesis Of 245-tri-aryl-1h-imidazolesmentioning

confidence: 99%

“…Subsequently, compound 170 was transformed to compound 171 by heating at 160 • C under N 2 atmosphere in dry N , N -dimethyl aminoethanol. Products 172-175 were obtained by a similar procedure, albeit, with the addition of the respective metal salts (ZnCH 3 COO 2 , CoCl 2 , CuCl 2 , NiCl 2 ) (Scheme 41) [159].…”

Section: Synthesis Of 245-tri-aryl-1h-imidazolesmentioning

confidence: 99%

Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles

2015

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Xanthenedione Substituted Metallophthalocyanines as an Efficient and Recyclable Catalyst for One–pot Three Component Synthesis of 3‐Substituted Indoles

et al. 2016

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An efficient one-pot methodology for the synthesis of 3-aminoalkylated indoles catalyzed by metallophthalocyanines has been developed via a three component Mannich type reaction with secondary amines, aldehydes and indoles. The newer catalysts i. e. metallophthalocyanines were synthesized by tetramerization of xanthenedione substituted phthalonitrile in anhydrous N,N-dimethylformamide by conventional heating and microwave conditions and were characterized by different spectroscopic techniques. The aggregation behaviors of these metallophthalocyanines were studied at different concentration in dimethyl sulfoxide and it was observed that these metallophthalocyanines show monomeric behavior in DMSO. The catalyst was separated from the reaction medium, characterized and was successfully reused up to five catalytic cycles. It was observed that the catalyst is stable in the catalytic system. Based on observations, a suitable reaction pathway is proposed for the current reaction.

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Synthesis, characterization and spectroscopic studies of novel peripherally tetra-imidazole substituted phthalocyanine and its metal complexes, the computational and experimental studies of the novel phthalonitrile derivative

Cited by 26 publications

References 61 publications

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles

Xanthenedione Substituted Metallophthalocyanines as an Efficient and Recyclable Catalyst for One–pot Three Component Synthesis of 3‐Substituted Indoles

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