Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine

topal, tufan

doi:10.35378/gujs.838992

Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine

Tufan TOPAL (Pamukkale Üniversitesi, Mühendislik Fakültesi, Kimya Bölümü, Denizli, Türkiy)

Gazi University Journal of Science

4 2

Yıl: 2022 Cilt: 35 Sayı: 2 Sayfa Aralığı: 404 - 419 Metin Dili: İngilizce DOI: 10.35378/gujs.838992 İndeks Tarihi: 08-11-2022

Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine

Öz:

3-chloro-2-{(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine (HL) was prepared and its structure elucidated by LC/MS-MS, $^1H and ^{13}C$-NMR, UV-Vis, elemental analysis, FT- Raman and FT-IR. All theoretical calculations and optimized geometry were obtained from the 6-31G(d,p) basis set calculations. Calculated and scaled data of the molecule were compared with the observed FT-Raman and FT-IR spectroscopic data. The theoretical chemical shifts of the HL were performed in chloroform by using the same level with the GIAO method. The UV-Vis analyses of the HL were carried out at three different concentrations in chloroform and ethanol solvents and between 240-440 nm; the calculations of UV-Vis spectra analyses were performed via the TD-DFT method. The charge transfer and hyperconjugative and conjugative interactions were analyzed using the NBO analysis. Furthermore, frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) were also measured using the same method. This work provides a comprehensive electronic properties, vibration analysis and structural information of the title compund.

Anahtar Kelime: DFT calculations Gaussian 09W FT-Raman Hydrazone Pyridine

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

[1] Adly, O. M. I., and Emara, A. A. A., "Spectroscopic and biological studies of new binuclear metal complexes of a tridentate ONS hydrazone ligand derived from 4-amino-6-methyl-3-thioxo-3,4- dihydro-1,2,4-triazin-5(2H)-one and 4,6-diacetylresorcinol", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 132: 91-101, (2014).
[2] Clark, N. A., Coleman, D., and Maclennan, J. E., "Electrostatics and the electro-optic behaviour of chiral smectics C: ‘block’ polarization screening of applied voltage and ‘V-shaped’ switching", Liquid Crystals, 27: 985–990, (2000).
[3] Da Cunha Areias, M. C., Ávila-Terra, L. H. S., Gaubeur, I., and Suárez-Iha, M. E. V., "A new simultaneous spectrophotometric method for determination of iron(II) and iron(III) in natural waters", Spectroscopy Letters, 34: 289–300, (2001).
[4] Rollas, S., and Küçükgüzel, Ş. G., "Biological activities of hydrazone derivatives", Molecules, 12: 1910–1939, (2007).
[5] Karadeniz, Ş., Ataol, C. Y., Şahin, O., İdil, Ö., and Bati, H., "Synthesis, structural studies and antimicrobial activity of N’-((2Z, 3E)-3-(hydroxyimino)butan-2-ylidene)-2-phenylacetohydrazide and its Co(II), Ni(II) complexes", Journal of Molecular Structure, 1161: 477–485, (2018).
[6] Schlosser, M., and Mongin, F., "Pyridine elaboration through organometallic intermediates: regiochemical control and completeness", Chemical Society Reviews, 36: 1161–1172, (2007).
[7] Mohamed Asath, R., Premkumar, R., Mathavan, T., and Milton Franklin Benial, A., "Structural, spectroscopic and molecular docking studies on 2-amino-3-chloro-5-trifluoromethyl pyridine: A potential bioactive agent", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 175: 51–60, (2017).
[8] Uzun, S., Demircioğlu, Z., "Bis[2-(metilamino)troponato]bakır(II) Molekülünün Yapısal ve Elektronik Özelliklerinin Deneysel ve Kuramsal Analizleri", Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, 15: 9–22, (2020).
[9] Topal, T., Kart, H. H., Tunay Taşlı, P., and Karapınar, E., "Synthesis and structural study on (1E,2E,1′E,2′E)-3,3′-bis[(4-bromophenyl)-3,3′-(4-methy-1,2-phenylene diimine)] acetaldehyde dioxime: A combined experimental and theoretical study", Optics and Spectroscopy, 118: 897–912, (2015).
[10] Malik, M., Wysokiński, R., Zierkiewicz, W., Helios, K., and Michalska, D., "Raman and infrared spectroscopy, DFT calculations, and vibrational assignment of the anticancer agent picoplatin: performance of long-range corrected/hybrid functionals for a platinum(II) complex", The Journal of Physical Chemistry A, 118: 6922-6934, (2014).
[11] Albayati, M. R., Kansız, S., Dege, N., Kaya, S., Marzouki, R., Lgaz, H., Salghi, R., Ali, Ismat., Alghamdi, M. M., Chung, III-Min., "Synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations of 2-[(2,3-dimethylphenyl)amino]-N’-[(E)-thiophen-2-ylmethylidene]benzohydrazide", Journal of Molecular Structure, 1205, 127654, (2020).
[12] Topal, T., "Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds", Acta Chimica Slovenica, 68: 88-101, (2020).
[13] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J.,Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M. , Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. and Fox, D. J. Gaussian, Inc., Gaussian 09, Revision D.01, Wallingford CT, (2013).
[14] Kohn, W. and Sham, L. J., "Self-Consistent Equations Including Exchange and Correlation Effects", Physical Review, 140: A1133-A1138, (1965).
[15] Vladimiroff, T., "A density functional study of s-trinitrobenzene", Journal of Molecular Structure: Theochem, 453: 119–122, (1998).
[16] Panicker, C. Y., Ambujakshan, K. R., Varghese, H. T., Mathew, S., Ganguli, S., Nanda, A. K., and Alsenoy, C. V., "FT-IR, FT-Raman and DFT calculations of 3-{[(4-fluorophenyl)methylene] amino}-2-phenylquinazolin-4(3H)-one", Journal of Raman Spectroscopy, 40: 527–536, (2009).
[17] Jamróz, M. H., "Vibrational energy distribution analysis (VEDA): scopes and limitations", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,114: 220–230, (2013).
[18] Wolinski, K., Hinton, J. F., and Pulay, P., "Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations", Journal of the American Chemical Society, 112: 8251–8260, (1990).
[19] Casida, M. E., Casida, K. C., and Salahub, D. R., "Excited-state potential energy curves from time- dependent density-functional theory: A cross section of Formaldehyde’s 1A1 manifold", International Journal of Quantum Chemistry, 70: 919–924, (1998).
[20] Glendening, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F., NBO Version 3.1, (2003).
[21] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A. V., Bloino, J., Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., Izmaylov, A. F., Sonnenberg, J. L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V. G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M. J., Heyd, J. J., Brothers, E. N., Kudin, K. N., Staroverov, V. N., Keith, T. A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A. P., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Millam, J. M., Klene, M., Adamo, C., Cammi, R., Ochterski, J. W., Martin, R. L., Morokuma, K., Farkas, O., Foresman, J. B., Fox, D. J. Gaussian, Inc., Gaussian 16, Revision A.03, Wallingford CT, (2016).
[22] Dennington, Roy; Keith, Todd A.; Millam, John M. Semichem Inc., GaussView, Version 6, Shawnee Mission, KS, (2016).
[23] Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., Montgomery Jr, J.A., "General atomic and molecular electronic structure system", Journal of Computational Chemistry, 14: 1347– 1363, (1993).
[24] Puviarasan, N., Arjunan, V., and Mohan, S., "FT-IR and FT-Raman studies on 3- aminophthalhydrazide and N-aminophthalimide", Turkish Journal of Chemistry, 26: 323–333, (2002).
[25] Arslan, H., Algül, O., and Onkol, T., "Vibrational spectroscopy investigation using ab initio and density functional theory analysis on the structure of 3-(6-benzoyl-2-oxobenzo[d]oxazol-3(2H)- yl)propanoic acid", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 70: 606-614, (2008).
[26] Sas, E. B., Kurt, M., Can, M., Horzum, N., and Atac, A., "Spectroscopic studies on 9H-carbazole-9- (4-phenyl) boronic acid pinacol ester by DFT method", Journal of Molecular Structure, 1118: 124– 138, (2016).
[27] Bieńko, D., Malik-Gajewska, M., Walencik, P., Kaj, M., Zierkiewicz, W., Murtaza, G., Ruffer, T., Ahmad, S., "IR and Raman spectroscopic analysis, DFT modeling, and magnetic properties of a nickel(II) complex, [Ni(succ)(H2O)4]n", Journal of Coordination Chemistry, 72: 2215–2232, (2019).
[28] Ramalingam, S., Periandy, S., Mohan, S., "Vibrational spectroscopy (FTIR and FTRaman) investigation using ab initio (HF) and DFT (B3LYP and B3PW91) analysis on the structure of 2- amino pyridine", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 77: 73– 81, (2010).
[29] Wilmshurst, J., and Bernstein, H., "The vibrational spectra of pyridine, pyridine-4-d, pyridine-2,6- d2, and pyridine-3,5-d2", Canadian Journal of Chemistry, 35: 1183–1194, (2011).
[30] Karabacak, M., Sinha, L., Prasad, O., Asiri, A. M., Cinar, M., Shukla, V.K., "FT-IR, FT-Raman, NMR, UV and quantum chemical studies on monomeric and dimeric conformations of 3,5-dimethyl- 4-methoxybenzoic acid", Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., 123: 352–362, (2014).
[31] Colthup, N., "Introduction to infrared and Raman spectroscopy", Elsevier, (2012).
[32] Boopathi, M., Udhayakala, P., Devi, T.S.R., Rajendiran, T. V., "Vibrational spectroscopic (FT-IR , FT-Raman and NMR) and DFT analysis of 2-methoxy-3-(trifluoromethyl) pyridine", Journal of Chemical and Pharmaceutical Research, 7: 1172–1183, (2015).
[33] Agarwal, P., Choudhary, N., Gupta, A., Tandon, P., "Density functional theory studies on the structure, spectra (FT-IR, FT-Raman, and UV) and first order molecular hyperpolarizability of 2- hydroxy-3-methoxy-N-(2-chloro-benzyl)-benzaldehyde-imine: Comparison to experimental data", Vibrational Spectroscopy, 64: 134–147, (2013).
[34] Muthu, S., and Elamurugu Porchelvi, E., "FT-IR, FT-RAMAN, NMR, spectra, normal co-ordinate analysis, NBO, NLO and DFT calculation of N, N-diethyl-4-methylpiperazine-1-carboxamide molecule", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 115: 275–286, (2013).
[35] Topal, T., and Karapınar, E., "Synthesis and characterization of new homo and heteronuclear schiff base copper(II) complexesJournal of the Turkish Chemical Society Section A: Chemistry, 5: 785– 802, (2018).
[36] Oltean, M., Calborean, A., Mile, G., Vidrighin, M., Iosin, M., Leopold, L., Maniu, D., Leopold, N., Chis, V., "Absorption spectra of PTCDI :", A combined UV–Vis and TD-DFT study", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97: 703–710, (2012).
[37] Madhankumar, S., Muthuraja, P., and Dhandapani, M., "Structural characterization, quantum chemical calculations and Hirshfeld surface analysis of a new third order harmonic organic crystal: 2-Amino-4-methylpyridinium benzilate", Journal of Molecular Structure, 1201: 127151, (2020).
[38] Topal, T., "Synthesis and characterization of zinc(II) complexes with new pyridine-based ligands: crystal structure, Hirshfeld surface analysis, and molecular docking study of lung cancer cell", Journal of Coordination Chemistry, 73: 3203–3222, (2020).
[39] Babur Şaş, E., and Kurt, M., "5-Bromo-1H Benzimidazolun Ft-Raman, Ft-Ir, Nmr ve Dft Hesaplamaları", SAÜ Fen Bilimleri Enstitüsü Dergisi, 21, (2017).
[40] Fukui, K., "Role of frontier orbitals in chemical reactions", Science (80), 218: 747–754, (1982).
[41] Karakurt, T., "3-[(E)-2-(4-fenil-1,3-tiyazol-2-yl)hidrazin-1-yiliden]-indolin-2-on bileşiğinin Tautomer Yapısı Üzerinde Gaz ve Katı Fazında Teorik Hesaplamalar", Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, 20: 96–102, (2020).
[42] Arivazhagan, M., and Meenakshi, R., "Vibrational spectroscopic studies and DFT calculations of 4- bromo-o-xylene", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 91: 419– 430, (2012).
[43] Kumar, M., Kariem, M., Sheikh, H.N., Frontera, A., Seth, S.K., Jassal, A.K., "A series of 3D lanthanide coordination polymers decorated with a rigid 3,5-pyridinedicarboxylic acid linker: syntheses, structural diversity, DFT study, Hirshfeld surface analysis, luminescence and magnetic properties", Dalton Transactions, 47: 12318–12336, (2018).
[44] Prabavathi, N., Nilufer, A., and Krishnakumar, V., "FT-IR, FT-Raman and DFT quantum chemical study on the molecular conformation, vibrational and electronic transitions of 1-(m-(trifluoromethyl) phenyl)piperazine", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 121: 483–493, (2014).
[45] Islam, S. K. N., "Conceptual Density Functional Theory and its Application in the Chemical Domain", (2018).
[46] Salzner, U., Baer, R., "Koopmans’ springs to life", The Journal of Chemical Physics, 131, (2009).
[47] Venkateshan, M., Priya, R.V., Muthu, M., Suresh, J., Kumar, R.R., "Crystal structure, Hirshfeld surface analysis, DFT calculations and molecular docking studies on pyridine derivatives as potential inhibitors of NAMPT", Chemical Data Collections, 23: 100262, (2019).
[48] Guerrab, W., Lgaz, H., Kansız, S., Mague, J., Ansar, M., Marzouki, R., Taoufik, J., Ali, I., Chung, M. Ramli, Y., "Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations", Journal of Molecular Structure, 1205: 127630, (2019).
[49] Murray, J. S., and Sen, K., "Molecular electrostatic potentials: concepts and applications", Elsevier, (1996).
[50] Munshi, P., and Guru Row, T. N., "Intra- and intermolecular interactions in small bioactive molecules: cooperative features from experimental and theoretical charge-density analysis", Acta Crystallographica Section B: Structural Science, 62: 612–626, (2006).

APA	topal t (2022). Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. , 404 - 419. 10.35378/gujs.838992
Chicago	topal tufan Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. (2022): 404 - 419. 10.35378/gujs.838992
MLA	topal tufan Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. , 2022, ss.404 - 419. 10.35378/gujs.838992
AMA	topal t Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. . 2022; 404 - 419. 10.35378/gujs.838992
Vancouver	topal t Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. . 2022; 404 - 419. 10.35378/gujs.838992
IEEE	topal t "Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine." , ss.404 - 419, 2022. 10.35378/gujs.838992
ISNAD	topal, tufan. "Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine". (2022), 404-419. https://doi.org/10.35378/gujs.838992

APA	topal t (2022). Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. Gazi University Journal of Science, 35(2), 404 - 419. 10.35378/gujs.838992
Chicago	topal tufan Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. Gazi University Journal of Science 35, no.2 (2022): 404 - 419. 10.35378/gujs.838992
MLA	topal tufan Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. Gazi University Journal of Science, vol.35, no.2, 2022, ss.404 - 419. 10.35378/gujs.838992
AMA	topal t Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. Gazi University Journal of Science. 2022; 35(2): 404 - 419. 10.35378/gujs.838992
Vancouver	topal t Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine. Gazi University Journal of Science. 2022; 35(2): 404 - 419. 10.35378/gujs.838992
IEEE	topal t "Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine." Gazi University Journal of Science, 35, ss.404 - 419, 2022. 10.35378/gujs.838992
ISNAD	topal, tufan. "Spectroscopic and Quantum Chemical Studies on the Structure of 3-chloro-2- {(2Z)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl}pyridine". Gazi University Journal of Science 35/2 (2022), 404-419. https://doi.org/10.35378/gujs.838992