Investigation on Molecular Structure, Vibrational Analysis and Thermodynamic Properties of 1-(2,6-dimethylmorpholine-4-yl-methyl)-3-methyl-4-[3-ethoxy-(4-benzenesulfonyloxy)- benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one

Year 2019, Volume: 3 Issue: 2, 76 - 85, 15.12.2019

Hilal Medetalibeyoğlu Haydar Yüksek Gül Özdemir

https://doi.org/10.33435/tcandtc.469783

Cited By: 1

Abstract

In
this article, 1-(2,6-dimethylmorpholine-4-yl-methyl)-3-methyl-4-[3-ethoxy-(4-benzenesulfonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one has been theoretically studied. All quantum chemical
calculations were carried out by using Gaussian 09W program package and
GaussView molecular visualization program. The
¹H and ¹³C NMR chemical shifts of the title molecule were
calculated by the GIAO method and compared with experimental results. Theoretical
and experimental values were plotted according to dexp=a+b.
d
calc. The standard error values were found via the Sigma plot with regression
coefficient of a and b constants. The vibrational frequency values of this
compound have been calculated by using 6-31G(d,p) basis set with DFT and HF
methods and these values are multiplied with appropriate adjustment factors.
The veda4f program was used in defining IR data. The polarizability (α), hyperpolarizability (β), dipole moment along
with molecular electrostatic potential surface have been calculated. The
molecular electrostatic potential (MEP) map was calculated to assign reactive
site on the surface of the molecule. The calculated electronic, structural (bond
lengths and bond angles)  and several
thermodynamic parameters of title molecule were performed using the
Hartree-Fock (HF) and density functional methods (DFT/B3LYP) with 6-31G(d,p)
basis set.

Keywords

mannich bases, GIAO, DFT(B3LYP), 6-31G(d, p) basis set

References

• References [1] F. Lopes, R. Capela, J.O. Goncaves, P.N. Horton, M.B. Hursthouse, J. Iley, C.M. Casimiro, J. Bom, R. Moreira, Amidomethylation of amodiaquine: antimalarial N-Mannich base derivativesTetrahedron Letters, 45 (2004) 7663-7666.
• [2] B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles, European Journal of Medicinal Chemistry, 38 (2003) 759-767.
• [3] K. Kucukoglu, M. Gul, M. Atalay, E. Mete, C. Kazaz, O. Hanninen, H.I. Gul, Synthesis of some Mannich bases with dimethylamine and their hydrazones and evaluation of their cytotoxicity against Jurkat cells, Arzneimittelforschung 61 (2011) 366-371.
• [4] H.I. Gul, J. Vepsalainen, M. Gul, E. Erciyas, O. Hanninen, Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cells, Pharmaceutica Acta Helvetiae, 74(2000) 393-398.
• [5] J.R. Dimmock, E. Erciyas, S.K. Raghavan, D.L. Kirkpatrick, Evaluation of the cytotoxicity of some Mannich bases of acetophenone against the EMT6 tumour, Pharmazie 45 (1990) 755-757.
• [6] A.P. Liesen, T.M. Aquino, C.S. Carvalho, V.T. Lima, J.M. Araujo, J.G. Lima, A.R. Faria, E.J. T.Melo, A.J. Alves, E.W. Alves, A.Q. Alves, A.S. Goes, Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles, European Journal of Medicinal Chemistry, 45 (2010) 3685-3691.
• [7] S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin, A. Ozbek, Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds, European Journal of Medicinal Chemistry, 37 (2002) 197-206.
• [8] A. Kumar, C.S. Rajput, S.K. Bhati, Synthesis of 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent, Bioorganic & Medicinal Chemistry, 15 (2007) 3089-3096.
• [9] J. Balzarini, B. Orzeszko, J.K. Maurin, A. Orzeszko, Synthesis and anti-HIV studies of 2-adamantyl-substituted thiazolidin-4-ones, European Journal of Medicinal Chemistry, 42 (2007) 993-1003.
• [10] J. Balzarini, B. Orzeszko-Krzesinska, J.K. Maurin, A. Orzeszko, Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones, European Journal of Medicinal Chemistry, 44 (2009) 303-311.
• [11] B.R. Bhattarai, B. Kafle, J. Hwang, D. Khadka, S. Lee, J. Kang, S.W. Ham, I. Han, H. Park, H. Cho, Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects, Bioorganic & Medicinal Chemistry, 19 (2009) 6161-6165.
• [12] B.A. Bhat, S. Ponnala, D.P. Sahu, P. Tiwari, B.K. Tripathi, A.K. Srivastava, Synthesis and antihyperglycemic activity profiles of novel thiazolidinedione derivatives, Bioorganic & Medicinal Chemistry, (2004) 12 5857-5864.
• [13] C. M. Jackson, B. Blass, K. Coburn, L. Djandjighian, G. Fadayel, A. J. Fluxe, S. J. Hodson, J. M. Janusz, M. Murawsky, J. M. Ridgeway, R. E. White, S. Wu, Evolution of thiazolidine-based blockers of human Kv1.5 for the treatment of atrial arrhythmias, Bioorganic & Medicinal Chemistry Letters, 17 (2007) 282-284.
• [14] V. P. Petrović, D. Simijonović, S. B. Novaković, G. A. Bogdanović, S. Marković, Z. D. Petrović, Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study, Journal of Molecular Structure, 1098 (2015) 34-40.
• [15] P. E. Hansen, J. Spanget-Larsen, Structural studies on Mannich bases of 2-Hydroxy-3,4,5,6-tetrachlorobenzene. An UV, IR, NMR and DFT study. A mini-review, Journal of Molecular Structure, 1119 (2016) 235-239.
• [16] H. Li, A. Fu, H. Shi, Theoretical studies of stereoselectivities in the direct organocatalytic Mannich reactions involving ketimine, Journal of Molecular Catalysis A: Chemical, 303 (2009) 1–8.
• [17] M. Pagacz-Kostrzewa, R. Bronisz, M. Wierzejewska, Theoretical and matrix isolation FTIR studies of 3-amino-1,2,4-triazole and its isomers, Chemical Physics Letters, 473 (2009) 238–246.
• [18] A. S. Al-Tamimi, Electronic structure, hydrogen bonding and spectroscopic profile of a new 1,2,4-triazole-5(4H)-thione derivative: A combined experimental and theoretical (DFT) analysis, Journal of Molecular Structure, 1120 (2016) 215-227.
• [19] A. O. Ayeni, G. M. Watkins E. C. Hosten, Polymorphism of a new Mannich base - [-4-methyl-2-((4-(4-nitrophenyl)piperazin-1-yl)methyl)phenol], Journal of Molecular Structure, 1160 (2018) 38-45.
• [20] A. D. Raj, M. Jeeva, M. Shankar, G. V. Prabhu, M. Vimalan, I. V.Potheher, Synthesis, growth, physicochemical properties and DFT calculations of 2-naphthol substituted Mannich base 1-(morpholino(phenyl) methyl) naphthalen-2-ol: A non linear optical single crystal, Journal of Molecular Structure, 1147 (2017) 763-775.
• [21] M. S. Boobalan, M. Amaladasan, S. Ramalingam, D. Tamilvendan, G. V. Prabhu, M. Bououdina, First principles and DFT supported investigations on vibrational spectra and electronic structure of 2-((phenylamino)methyl)isoindoline-1,3-dione–An antioxidant active Mannich base, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137 (2015) 962–978.
• [22] A. Fu, H. Li, H. Si, S. Yuan, Y. Duan, Theoretical studies of stereoselectivities in the direct syn- and anti-Mannich reactions catalyzed by different amino acids, Tetrahedron: Asymmetry 19 (2008) 2285–2292.
• [23] J. Pająk, M. Rospenk, G. Maes, L. Sobczyk, Matrix-isolation FT-IR and DFT theoretical studies of the intramolecular hydrogen bonding in Mannich bases, Chemical Physics, 320 (2006) 229–238.
• [24] R. I. Al-Wabli, M. Govindarajan, M. S. Almutairi, M. I. Attia, Spectral characterization, computed frequencies analysis and electronic structure calculations on (1E)-N-hydroxy-3-(1H-imidazol- 1-yl)-1-phenylpropan-1-imine: An oxime-bearing precursor to potential antifungal agents, Journal of Molecular Structure, 1168 (2018) 264-279.
• [25] A. Diez-Martinez, T. Tejero, P. Merino, Experimental and theoretical studies on Mannich-type reactions of chiral non-racemic N-(benzyloxyethyl) nitrones, Tetrahedron: Asymmetry 21 (2010) 2934–2943.
• [26] M. H. Jamróz, Vibrational energy distribution analysis: VEDA 4 program, Warsaw, 2004.
• [27] R. John Xavier, E. Gobinath, Spectroscopic investigations, quantum chemical calculations, HOMO-LUMO and NBO/NLMO analysis of 4-pyridinecarbohydrazide, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 115 (2013) 815–822.
• [28] C. Karunakaran, P.Anilkumar, P.Vinayagamoorthy, Lack of enhanced photocatalytic formation of iodine on particulate semiconductor mixtures, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 98 (2012) 460-465.
• [29] K. Wolinski, J.F. Hinton, P. Pulay, Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society 112 (23), 1990.
• [30] A. Kolla, V. Parasuk, W. Parasuk, A. Karpfen, P. Wolschann, Theoretical study on the intramolecular hydrogen bond in chloro-substituted N,N-dimethylaminomethylphenols. I. Structural effects, Journal of Molecular Structure 690 (2004) 165–174.
• [31] S. J. Pradeepa, D. Tamilvendan, M. S. Boobalan, N. Sundaraganesan, Vibrational and structural observations upon 3-((1H-benzo[d]imidazol-1-yl)methyl)naphthalen-2-ol from spectral and DFT computing approaches, Journal of Molecular Structure 1112 (2016) 33-44.
• [32] Ö. Tamer, M. H. Bhatti, U. Yunus, D. Avcı, Y. Atalay, M. Nadeem, S. R. Shah, M. Helliwell Structural, spectroscopic, nonlinear optical and electronic properties of calcium N-phthaloylglycinate: A combined experimental and theoretical study, Journal of Molecular Structure 1125 (2016) 315-322.
• [33] R. J. Fessenden, J. S. Fessenden, Organic Chemistry, Third Edition, Brooks, Cole Publishing Company, California, 1986.
• [34] A .A. İkizler, Organik Kimyaya Giriş, Dördüncü Baskı, KTÜ Basımevi, Trabzon, Türkiye, 1996, 398s.
• [35] R. M. Silverstein, F. X. Webster, D. J. Kiemle, Spectrometric identification of organic compounds, John Wiley & Sons, 2014.