Experimental and Theoretical Studies, Spectral (FT-IR, NMR) and NBO Analysis of 4-(3-2,4-Dichlorophenyl)Triaz-1-enyl) Benzamide

Document Type : Research Article


1 College of Engineering, University of Tehran, Tehran, I.R. IRAN

2 Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, I.R. IRAN

3 Department of Chemistry, Mianeh Branch, Islamic Azad University, Mianeh, I.R. IRAN

4 Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, I.R. IRAN


Abstract-4-(3-(2,4-Dichlorophenyl)triaz-1-enyl)benzamide, CTB, was synthesized and characterized using IR and NMR (1H and 13C) spectroscopy. The optimized geometry, vibrational wave numbers, 1H and 13C chemical shift values and NBO parameters of CTB were computed with Density Functional Theory (DFT/PBE1PBE) and Hartree-Fock (HF) methods using 6-311+G(2d,p) basis set. The harmonic vibrational wavenumbers were calculated and their scaled values were compared with the experimental FT-IR spectrum. A detailed interpretation of the NMR spectra of CTB was reported. The calculated data are in reasonably good agreement with the experimental measurements. Moreover, the logP value and thermodynamic properties were estimated with ChemBioOffice Ultra 11.0, ACD/LogP and ALOGPS programs. The NBO analysis was carried out for CTB.


Main Subjects

[1] Griess P., On New Nitrogenous Derivatives of the Phenyl- and Benzoyl-Series, Proc. Royal Soc. London, 9: 594–597 (1857).
[2] Enders D., Rijksen C., Köbberling E.B., Gillner A., Köbberling, A Triazene-Based New Photolabile Linker in Solid Phase Chemistry, J. Tetrahedron Lett., 45: 2839–2841 (2004).
[4] Santos A.J.R.W.A., Hörner R., Paraginski G.L., Machado F.C., Hörner M., Crystal Structure of 3-Phenyl-1-methyltriazene 1-oxide, Anal. Sci., 23: x251–x252 (2007).
[5] Iglesias B.A., Hörner M., Toma H.E., Araki K., 5-(1-(4-phenyl)-3-(4-nitrophenyl)triazene)-10,15,20-triphenylporphyrin, J. Porphyrins, Phthalocyanines, 16: 200–209 (2012).
[6] Oliveira G.M., Hörner M., Machado A., Back D.F., Monteiro J.H.S.K., Davolos M.R.,New Chelate Complexes of Trivalent Y and Lanthanides (Eu, Ho, Yb) with a Triazene N-Oxide: Synthesis, Structural Characterization and Luminescence Properties, Inorg. Chim. Acta., 366: 203–208 (2011).
[7] Kimball D.B., Herges R., Haley M.M., Two Unusual, Competitive Mechanisms for (2-Ethynylphenyl)triazene Cyclization:  Pseudocoarctate versus Pericyclic Reactivity,  J. Am. Chem. Soc., 124: 1572-1573 (2002).
[8] Zhao P., Zhang Z., Wang P. J., Liu D.S., 1,3-diphenyltriazene as a Possible Optical Molecular Switch: A First-Principles Study, Physica B, 404: 3462-   (2009).
[9] Khani H., Rofouei M.K., Arab P., Gupta V.K., Vafaei Z., Multi-Walled Carbon Nanotubes-Ionic Liquid-Carbon Paste Electrode as a Super Selectivity Sensor: Application to Potentiometric Monitoring of Mercury Ion(II), J. Hazard. Mater., 183: 402–409 (2010).
[10] Frisch M.J., et al., “Gaussian 03 Revision C.02”, Gaussian Inc., Pittsburgh, PA, (2003).
[11]  Jeffrey P. Merrick, Moran D., Radom L., An Evaluation of Harmonic Vibrational Frequency Scale Factors, J. Phys. Chem. A, 111: 11683-11700 (2007).
[12] ACD/HNMR and ACD/CNMR; “Advanced Chemistry Development”, Inc., http://www.acdlabs.com.
[13] Oboyle N.M., Tenderholt A.L., Langner K.M., cclib: A Library for Package-Independent Computational Chemistry Algorithms, J. Comput. Chem., 29: 839-845 (2008).
[14] Domingues V.O., Hörner R., Reetz L.G.B., Kuhn F., Coser V.M., Rodrigues J.N., Bauchspiess R., Pereira W.V., Paraginski G.L., Locatelli A., Fank J.O., Giglio V.F., Hörner M., In Vitro Evaluation of Triazenes: DNA Cleavage, Antibacterial Activity and Cytotoxicity Against Acute Myeloid Leukemia Cells, J. Braz. Chem. Soc., 21:  2226-2237 (2010).
[15] Melardi M.R., Aghamohamadi M., Gharamaleki J.A., Rofouei M.K., Notash B., 1-(3,5-Dichlorophenyl)-3-(2-methoxyphenyl)triaz-1-ene, Acta Cryst., E68, o724 (2012).
[16] Fereyduni E., Vessally E., Yaaghubi E., Sundaraganesan N., One-Pot Synthesis, FT-IR, NMR and Density Functional Method (B3LYP) Studies on 2-(cyclohexylamino)-2-oxo-1-(pyridin-2-yl)ethyl Benzoate, Spectrochim. Acta A, 81: 64–71 (2011).
[17] Vessally E., Fereyduni E., Erdogdu Y., Habibi A., Eskandari K., Gulluoglu M.T., Synthesis, Spectroscopic and DFT Investigation of Dimethyl-2-(5-acetyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(triphenylphosphinylidene)Succinate, J. Mol. Struct., 985: 120–127 (2011).
[18] Chem Bio Draw Ultra, Version 11.0, Available from CambridgeSoft.