Novel 1-(4-chlorophenyl)-3-(2-ethoxyphenyl)triazene ligand: Synthesis, X-ray crystallographic studies, spectroscopic characterization and DFT calculations

Document Type : Research Article

Authors

Department of Chemistry, Payame Noor University, Tehran, Iran

Abstract

In the present work, a combined theoretical and experimental investigation on the properties of 1-(4-chlorophenyl)-3-(2-ethoxyphenyl)triazene is reported. The optimized geometry was calculated by B3LYP method using 6-311++G(2d,p) as a large basis set. The FT-IR spectrum was calculated at this level of theory, and was interpreted in terms of potential energy distribution (PED) analysis. The scaled theoretical frequencies were in line with the experimental ones. Furthermore, natural bond orbital (NBO) and atoms in molecules (AIM) theories were used to characterize intra-molecular hydrogen bond. The low value of charge transfer and the absence of bond critical point between O···HN show that there is not intra-molecular hydrogen bond.

Graphical Abstract

Novel 1-(4-chlorophenyl)-3-(2-ethoxyphenyl)triazene ligand: Synthesis, X-ray crystallographic studies, spectroscopic characterization and DFT calculations

Keywords


[1] N. C. Monica Barra, I. Lee, N. Chahal, Substituent Effects on the Thermal Cis-to-Trans Isomerization of 1,3-Diphenyltriazenes in Aqueous Solution. J. Org. Chem. 67 (2002) 2271-2277.
[2] D. S. Moore, S. D. Robinson, Catenated Nitro genLigands Part II.1 Transition Metal Derivatives of Triazoles, Tetrazoles, Pentazoles, and Hexazine. Adv. Inorg. Chem., 32 (1988) 171-239.
[3] R. Meldola, F. W. Streatfield, LXXII.—Notes on anhy-dro-bases. I. Ethenyltriamidonaphthalene. J. Chem. Soc., 51 (1887) 691-700.
[4] M. K. Rofouei J. A. Gharamaleki, E. Fereyduni, A. Aghaei, G. Bruno, H. A. Z. Rudbari, Structural and Solution Studies of two Mercury (II) Complexes with [1, 3‐Bis (2‐ethoxy) ben-zene] triazene. Anorg. Allg. Chem., 638 (2012) 220-223.
[5] G. A. Casagrande, E. Lang, G. M. de Oliveira, M. Hӧrner, F. Broch, Dealing with 1,3-bis(4-nitrophenyl)triazene as interme-diary ligand in the synthesis of polymeric (μ-Se)Hg-cluters: One-pot synthetic procedures and X-ray structural characteri-zation of [(PhSe)7Hg4BrPy]n. Inorg. Chim. Acta., 360 (2007) 1776-1779.
[6] K. Vrieze, G. Van Koten, Comprehensive Coordination Chemistry, Pergamon Press, Oxford, 1987.
[7] G. M. de Oliveira, M. Hӧrner, A. Machado, M. A. Villetti, D. F. Back, B. A. Iglesias, Stabilization of substituted triazene oxides by lanthanides chelation: Synthesis, TGA evaluations and X-ray structural features of [MIII{O2NPhNNN(O)Ph}4](Et3NH)·H2O (M = La3+, Dy3+; Et = C2H5). J. Mol. Struct., 928 (2009) 85-88.
[8] Bruker, SAINTPlus. Data Reduction and Correction Program v. 6.01, Bruker AXS, Madison, Wisconsin, USA, 1998.
[9] G. M. Sheldrick, SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction. Program, Bruker AXS, Mad-ison, Wisconsin, USA, 1998.
[10] G. M. Sheldrick, SHELXTL v. 5.10, Structure Determination Software Suite, BrukerAXS, Madison, Wisconsin, USA, 1998.
[11] Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Ba-boul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Walling-ford CT, 2004.
[12] NBO Version 3.1, E. D. Glendening, A. E. Reed, J. E. Car-penter, F. Weinhold,
[13] R. F. W. Bader, Atoms in Molecules, A Quantum Theory, Springer, UK, 1990.
[14] F. Biegler-König, J. Schönbohm, D. J. Bayles, AIM2000. Comput. Chem., 22 (2001) 545-559.
[15] M. H. Jamróz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw, 2004.
[16] N. M. O''Boyle, A. L. Tenderholt, K. M. Langner, A Library for Package-Independent Computational Chemistry Algo-rithms. J. Comp. Chem., 29 (2008) 839-845.
[17] F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic com-pounds. J. Chem. Soc., Perkin Trans., 2 (|1987) S1-S19.
[18] A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, R. Taylor, Supplement. Tables of bond lengths de-termined by X-ray and neutron diffraction. Part 2. Organo-metallic compounds and co-ordination complexes of the d-and f-block metals J. Chem. Soc., Dalton Trans., 12 (1989) S1-S83.
[19] M. P. Andersson, P. Uvdal, New Scale Factors for Harmonic Vibrational Frequencies Using the B3LYP Density Functional Method with the Triple-ζ Basis Set 6-311+G(d,p). J. Phys. Chem. 109 (2005) 2937-2941.
[20] V. K. Rastogi, M. A. Palafox, R. P. Tanwar, L. Mittal, 3,5-Difluorobenzonitrile: ab initio calculations, FTIR and Ra-man spectra. Spectrochim. Acta. A., 58 (2002) 1987-2004.
[21] M. Silverstein, G. C. Basseler, C. Morill, Spectrometric Identification of Organic Compounds, Wiley, New York, 1981.
[22] G. Keresztury, Raman Spectroscopy: Theory, in: Chalmers, J. M.; Griffiths P. R. (Eds.), Handbook of Vibrational Spectros-copy, Wiley, New York, 2002.
[23] V. Krishnakumar, N. Prabavathi, S. Muthunatesan, Density functional theory study of vibrational spectra, and assignment of fundamental vibrational modes of 1-bromo 4-fluoronaphthalene. Spectrochim. Acta. A., 70 (2008) 991-996.
[24] M. K. Rofouei, N. Sohrabi, M. Shamsipur; E. Fereyduni, S. Ayyappan, N. Sundaraganesan, X-ray crystallography charac-terization, vibrational spectroscopy, NMR spectra and quan-tum chemical DFT/HF study of N,N-di(2-methoxyphenyl)formamidine. Spectrochim.. Acta. A., 76 (2010) 182-190.
[25] E. Fereyduni, M. K. Rofouei, M. Kamaee, S. Ramalingam, S. M. Sharifkhani, Single crystal structure, spectroscopic (FT-IR, FT-Raman, 1H NMR, 13C NMR) studies, physico-chemical properties and theoretical calculations of 1-(4-chlorophenyl)-3-(4-nitrophenyl)triazene. Spectrochim. Acta. A. 90 (2012) 193-201.
[26] N. P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, Wiley, New York, 1994.
[27] G. Varsanyi, Vibrational spectra of benzene derivatives, Akademiai Kiado, Budapest, 1969.
[28] D. N. Sathyanarayana Vibrational spectroscopy theory and application, New Age, New Delhi, 2004.
[29] S. Periandy, S. Mohan, Proceedings National Academic Science, India, 68 (A), III (1998)
[30] V. R. Dani, Organic Spectroscopy, MacGraw Hill, New Delhi, 1995.
[31] H. Abdel-Shafy, H. Perlmutter, H. Kimmel, Vibrational studies of monosubstituted halogenated pyridines. J. Mol. Struct., 42 (1977) 37-49.
[32] L. E. Clougherty, Notes - C=N Stretching Frequency in Infrared Spectra of Aromatic Azomethines. J. Org. Chem., 22 (1957) 462.
[33] R. Kubler, R. W. Luttke, S. Z. Weckherlin, Electrochem. 64 (1960) 650.
[34] K. J. Morgan, Infrared spectra and structure of arylazonaph-thols. J. Chem. Soc., 20 (1961) 2151-2159.
[35] G. Socrates, Infrared and Raman characteristic group frequen-cies, Wiley, New York, 2001.
[36] L. G. Crane, D. Wang, L. M. Sears, B. Heynz, K. Carron, Anal. Chem. 67 (1995) 360.
[37] N. Sundaraganesan, J. Karpagam, S. Sebastian, J. P. Cornard, Spectrochimica Acta A 2009, 73, 11.
[38] R. Shanmugam, D. Sathyanarayana, The spectroscopic (FTIR, FT-IR gas phase and FT-Raman), first order hyperpolarizabili-ties, NMR analysis of 2,4-dichloroaniline by ab initio HF and density functional methods. Spectrochim. Acta. A., 40 (1984) 11-19.
[39] R. A. Yadav, I. S. Sing, Intermolecular hydrogen-bonding in o-ethyl and m-ethyl phenols. Ind. J. Pure Appl. Phys., 23 (1985) 626-627.
[40] G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, Adam Hilger, 1974.
[41] E. F. Mooney, The infra-red spectra of chloro- and bromo-benzene derivatives—II. Nitrobenzenes. Spectrochim. Acta. A., 20 (1964) 1021-1032.
[42] E. F. Mooney, The infrared spectra of chloro- and bromoben-zene derivatives—I: Anisoles and phenetoles. Spectrochim. Acta. A., 19 (1963) 877-877.
[43] F. Weinhold, C. R. Landis, Valency and bonding, Cambridge University Press, New York, 2005.