Synthesis, Characterization, and Theoretical Study of Some New Organotellurium Compounds Derived from Camphor

Nuha Hussain Al-Saadawy

doi:10.22146/ijc.69805

Synthesis, Characterization, and Theoretical Study of Some New Organotellurium Compounds Derived from Camphor

https://doi.org/10.22146/ijc.69805

Nuha Hussain Al-Saadawy^(1*)

(1) Department of Chemistry, College of Science, University of Thi-Qar, Thi-Qar, Iraq
(*) Corresponding Author

Abstract

The present work describes the synthesis of a variety of organotellurium compounds. The first part describes the synthesis of a new series of organotellurium compounds containing azomethine groups. Reaction of (E)-(4-((1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II)chloride and (E)-(5-methyl-2-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl) mercury(II)chloride with tellurium tetrabromide in 2:1 mole ratio yielded the tellurated Schiff bases Ar₂TeBr₂ (where Ar = 1-(C₉H₁₆C=N)C=N)C₆H₄ and 1-(C₉H₁₆C=N)C=N)-4-CH₃C₆H₃) respectively. Reduction of organyl tellurium dibromide Ar₂TeBr₂ by hydrazine hydrate obtained the corresponding tellurides (i.e., Ar₂Te) in good yields. Characterization of the prepared compounds was carried out using infrared spectrum (FT-IR), proton nuclear magnetic resonance spectrum (¹H-NMR), and elemental analysis (CHN). The molecular structure of the organotellurium compounds was investigated using the density functional theory with hybrid functional (B3LYP), and the basis set 6-31G Geometrical structure, HOMO surfaces, LUMO surfaces, and energy gap have been produced throughout the geometry optimization. The molecular geometry and contours for the organotellurium compounds were investigated throughout the geometrical optimization. The donor and acceptor properties have been studied by comparing organotellurium compounds' highest occupied molecular orbital energies (HOMO). The present study aims to prepare organotellurium compounds derived from aniline, p-toluidine, and camphor and their derivatives using tellurated Schiff bases.

Keywords

organotellurium; telluride; organyl tellurium dibromide; HOMO and LUMO energies; camphor; density functional theory

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References

[1] Al-Rubaie, A.Z., Al-Salim, N.I., and Al-Jadaan, S.A.N., 1993, Synthesis and characterization of new organotellurium compounds containing an ortho-amino group, J. Organomet. Chem., 443 (1), 67–70.

[2] Al‐Rubaie, A.Z., Al‐Masoudi, W.A., Al‐Jadaan, S.A.N., Jalbout, A.F., and Hameed, A.J., 2008, Synthesis, characterization, and computational study of some new organotellurium compounds containing azomethine groups, Heteroat. Chem., 19 (3), 307–315.

[3] Yamago, S., 2021, Practical synthesis of dendritic hyperbranched polymers by reversible deactivation radical polymerization, Polym. J., 53 (8), 847–864.

[4] Al-Saadawy, N.H., 2021, Synthesis, characterization and theoretical studies of new organotellurium compounds based on (4-(((1S,E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) chloride, Indones. J. Chem., 21 (6), 1443–1453.

[5] Yousif, T.Y., 2020, Preparation of some new organotellurium compounds derived from 4,-4-dihydroxy azobenzene, Coll. Basic Educ. Res. J., 16 (3), 892–898.

[6] Carrera Boutzis, E.I., 2017, Synthesis, Reactivity, and Photochemistry of π-Conjugated Tellurophenes, Dissertation, Department of Chemistry, University of Toronto, Canada.

[7] Aziz, F.K., Gazar, S.H., and Al-Saadawy, N.H., 2020, Simple, selective, and sensitive spectrophotometric method for determination of trace amounts of lead(II), cadmium(II), cobalt(II) with organomercury compounds, J. Global Pharma Technol., 12, 248–255.

[8] Al-Asadi, R.H., 2020, Synthesis and molecular structure study of new organotellurium and organomercury compounds based on 4-bromonaphthalen-1-amine, Russ. J. Gen. Chem., 90 (9), 1744–1749.

[9] Ahmed, W.M., Al-Saadawy, N.H., and Abowd, M.I., 2021, Synthesis and characterization of a new organoselenium and organotellurium compounds depending on 9-chloro-10-nitro-9,10-dihydroanthracene, Ann. Romanian Soc. Cell Biol., 25 (4), 11035–11043.

[10] Kadhim, M.A., and Al-Saadawy, N.H., 2021, Synthesis and characterization for some new organoselenium compounds depending on 8-hydroxyquinoline, Ann. Romanian Soc. Cell Biol., 25 (2), 2162–2172.

[11] Al-Saadawy, N.H., 2022, New organotellurium compounds based on camphor, aniline and p-toluidine: Preparation, characterization and theoretical study, Egypt. J. Chem., 65 (2), 19–27.

[12] Pop, A., Silvestru, C., and Silvestru, A., 2019, Organoselenium and organotellurium compounds containing chalcogen-oxygen bonds in organic synthesis or related processes, Phys. Sci. Rev., 4 (5), 20180061.

[13] Pop, A., Silvestru, C., and Silvestru, A., 2019, "3. Organoselenium and Organotellurium Compounds Containing Chalcogen-Oxygen Bonds in Organic Synthesis or Related Processes" in Selenium and Tellurium Reagents, Eds. Laitinen, R., and Oilunkaniemi, R., De Gruyter, Boston, 61–122.

[14] Tanini, D., and Capperucci, A., 2020, Unexpected ethyltellurenylation of epoxides with elemental tellurium under lithium triethylborohydride conditions, Chemistry, 2 (3), 652–661.

[15] Tanini, D., and Capperucci, A., 2019, Ring-opening reactions of heterocycles with selenium and tellurium nucleophiles, New J. Chem., 43 (29), 11451–11468.

[16] Irfan, M., Rehman, R., Razali, M.R., Ur Rehman, S., Ur Rehman, A., and Iqbal, M.A., 2020, Organotellurium compounds: an overview of synthetic methodologies, Rev. Inorg. Chem., 40 (4), 193–232.

[17] Al-Asadi, R.H., 2019, Synthesis, DFT calculation and biological activity of some organotellurium compounds containing azomethine group, Orbital: Electron. J. Chem., 11 (7), 402–410.

[18] Panda, A., and Behera, R.N., 2014, Comparative study of E⋯N (E=Se/Te) intramolecular interactions in organochalcogen compounds using density functional theory, J. Hazard. Mater., 269, 2–8.

[19] Diki, N.Y.S., Coulibaly, N.H., Kambiré, O., and Trokourey, A., 2021, Experimental and theoretical investigations on copper corrosion inhibition by cefixime drug in 1 M HNO₃ solution, J. Mater. Sci. Chem. Eng., 9, 11–28.

[20] Zhang, Z., Hu, M., Zhang, W., and Zhang, X., 2022, Construction of tellurium-doped mesoporous bioactive glass nanoparticles for bone cancer therapy by promoting ROS-mediated apoptosis and antibacterial activity, J. Colloid Interface Sci., 610, 719-730.

[21] Arora, A., Oswal, P., Rao, G.K., Kumar, S., Singh, A.K., and Kumar, A., 2021, Tellurium-ligated Pd(II) complex of bulky organotellurium ligand as a catalyst of Suzuki coupling: First report on in situ generation of bimetallic alloy ‘telluropalladinite’(Pd₉Te₄) nanoparticles and role in highly efficient catalysis, Catal. Lett., 1–13.

[22] Behera, R.N., and Panda, A., 2012, Nature of the Te⋯N intramolecular interaction in organotellurium compounds. A theoretical investigation by NBO and AIM methods, Comput. Theor. Chem., 999, 215–224.

[23] Kerbadou, R.M., Hadjadj Aoul, R., Benmaati, A., Taleb, A., Hacini, S., and Habib Zahmani, H., 2021, Identification of new biologically active synthetic molecules: Comparative experimental and theoretical studies on the structure-antioxidant activity relationship of cyclic 1,3-ketoamides, J. Mol. Model., 27 (4), 109.

[24] Silverstein, R.M., and Bassler, G.C., 1962, Spectrometric identification of organic compounds, J. Chem. Educ., 39 (11), 546.

[25] Bennett, A.J., Duke, C.B., and Silverstein, S.D., 1968, Theory of the tunneling spectroscopy of collective excitations, Phys. Rev., 176 (3), 969.

[26] Guthrie, R.D., 1978, Introduction to Spectroscopy (Pavia, Donald; Lampman, Gary M.; Kriz, George S., Jr.), J. Chem. Educ., 56 (10), A323.

[27] Scheinmann, F., 2013, An Introduction to Spectroscopic Methods for the Identification of Organic Compounds: Mass Spectrometry, Ultraviolet Spectroscopy, Electron Spin Resonance Spectroscopy, Nuclear Magnetic Resonance Spectroscopy (Recent Developments), Use of Various Spectral Methods Together, and Documentation of Molecular Spectra, Elsevier Science, Amsterdam, Netherlands.

[28] Pavia, D.L., Lampman, G.M., Kriz, G.S., and Vyvyan, J.A., 2014, Introduction to Spectroscopy, Cengage Learning, Boston, US.

[29] Oliveira, G.P., Barboza, B.H., and Batagin-Neto A., 2022, Polyaniline-based gas sensors: DFT study on the effect of side groups, Comput. Theor. Chem., 1207, 113526.

[30] Gusakova, J., Wang, X., Shiau, L.L., Krivosheeva, A., Shaposhnikov, V., Borisenko, V., Gusakov, V., and Tay, B.K., 2017, Electronic properties of bulk and monolayer TMDs: Theoretical study within DFT framework (GVJ‐2e method), Phys. Status Solidi A, 214 (12), 1700218.

[31] Fernandes, G.F.S., Pontes, M.A.P., Machado, F.B.C., and Ferrão, L.F.A., 2022, Electronic structure and stability of transition metal acetylacetonates TM(AcAc)_n (TM = Cr, Fe, Co, Ni, Cu; n = 1, 2, 3), Comput. Theor. Chem., 1207, 113502.

[32] Xavier, R.J., and Gobinath, E., 2012, FT-IR, FT-Raman, ab initio and DFT studies, HOMO–LUMO and NBO analysis of 3-amino-5-mercapto-1,2,4-triazole, Spectrochim. Acta, Part A, 86, 242–251.

[33] Arivazhagan, M., Manivel, S., Jeyavijayan, S., and Meenakshi, R., 2015, Vibrational spectroscopic (FTIR and FT-Raman), first-order hyperpolarizablity, HOMO, LUMO, NBO, Mulliken charge analyses of 2-ethylimidazole based on Hartree–Fock and DFT calculations, Spectrochim. Acta, Part A, 134, 493–501.

[34] Sheela, N.R., Muthu, S., and Sampathkrishnan, S., 2014, Molecular orbital studies (hardness, chemical potential, and electrophilicity), vibrational investigation and theoretical NBO analysis of 4-4′-(1H-1,2,4-triazol-1-yl methylene) dibenzonitrile based on ab initio and DFT methods, Spectrochim. Acta, Part A, 120, 237–251.

[35] Vennila, P., Govindaraju, M., Venkatesh, G., and Kamal, C., 2016, Molecular structure, vibrational spectral assignments (FT-IR and FT-RAMAN), NMR, NBO, HOMO-LUMO and NLO properties of O-methoxybenzaldehyde based on DFT calculations, J. Mol. Struct., 1111, 151–156.

[36] Muya, J.T., Donald, K.J., Ceulemans, A., and Parish., C., 2021, A comparison of the chemical bonding and reactivity of Si₈H₈O₁₂ and Ge₈H₈O₁₂: A theoretical study, J. Chem. Phys., 154, 164305.

[37] Vikramaditya, T., and Lin, S.T., 2017, Assessing the role of Hartree‐Fock exchange, correlation energy and long-range corrections in evaluating ionization potential, and electron affinity in density functional theory, J. Comput. Chem., 38 (21), 1844–1852.

[38] Xu, H., Xu, D.C., and Wang, Y., 2017, Natural indices for the chemical hardness/softness of metal cations and ligands, ACS Omega, 2 (10), 7185–7193.

DOI: https://doi.org/10.22146/ijc.69805