Othman HAMAD, Rebaz OBAID KAREEM, Omer KAYGILI

Density Function Theory Study of the Physicochemical Characteristics of 2-nitrophenol

2-Nitrophenol (2-NP) is utilized in the production of bio-refractory organic compounds, and petrochemicals, and in the synthesis of many drugs and weed killers. The chemical structure of 2-NP is C6H5NO3. The structure of 2-NP is important as the nitro group (NO2. In this present investigation, the Gaussian 5.0 program was used to compute the difference in energy level that exists between the HOMO and LUMO states of the BGs.This information was then used to optimize the shape of the 2-NP structures using DFT methods. The 3-21G/B3LYP base set has a minimum value for the BG energy of 3.48 eV. This is the minimum value that can be achieved. The DOS for 2-NP was measured to have its maximum possible value of 2.23 ev/atom. According to the results of the IR, and Raman spectrum, the C-H stretching vibration peak for 2-NP was found to be between 3208.96 cm-1 and 3243.76 cm-1. The maximum excitation energy was analyzed at a wavelength of 382.1 nm, and the oscillator strength was determined at 0.0537 UV Spectroscopy. In the potential energy map (PE), the colors are changed from blue to red in the range of -4.442e-2 to 4.442e-2.

Keywords:

Density Function Theory (DFT), HOMO-LUMO, The density of State (DOS), IR Raman spectrum, UV spectroscopy, Potential Energy (PE) map,

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[1] Wu, J.T., Zhang, J.G., Yin, X., He, P., and Zhang, T.L. (2014). Synthesis and Characterization of the Nitrophenol Energetic Ionic Salts of 5, 6, 7, 8‐Tetrahydrotetrazolo [1, 5‐b][1, 2, 4] triazine, European Journal of Inorganic Chemistry, 2014 (27), pp: 4690-4695.
[2] Allen, S.J., Koumanova, B., Kircheva, Z., and Nenkova, S. (2005). Adsorption of 2-nitrophenol by technical hydrolysis lignin: kinetics, mass transfer, and equilibrium studies, Industrial & engineering chemistry research, 44 (7), pp: 2281-2287.
[3] Aamir, M., Khan, M.D., Sher, M., Bhosale, S.V., Malik, M.A., Akhtar, J., and Revaprasadu, N. (2017). A facile route to cesium lead bromoiodide perovskite microcrystals and their potential application as sensors for nitrophenol explosives, European Journal of Inorganic Chemistry, 2017 (31), pp: 3755-3760.
[4] Reichelt, H., Faunce, C.A., and Paradies, H.H. (2015). Structures of the 2-nitrophenol alkali complexes in solution and the solid state, The Journal of Chemical Physics, 143 (4), pp: 044307.
[5] Ko, J.W., Park, S.H., Jeon, S., Chung, H., and Ko, W.B. (2022). Catalytic activity of C60 fullerene nanowhisker-silver nanoprism composite for reduction of 2-nitrophenol, Fullerenes, Nanotubes and Carbon Nanostructures, 30 (5), pp: 584-588.
[6] Baysal, G., Uzun, D., and Hasdemir, E. (2020). The fabrication of a new modified pencil graphite electrode for the electrocatalytic reduction of 2-nitrophenol in water samples, Journal of Electroanalytical Chemistry, 860 113893.
[7] Kupeta, A., Naidoo, E., and Ofomaja, A. (2018). Kinetics and equilibrium study of 2-nitrophenol adsorption onto polyurethane cross-linked pine cone biomass, Journal of Cleaner Production, 179 191-209.
[8] Buemi, G. (2002). Ab initio DFT study of the rotation barriers and competitive hydrogen bond energies (in gas phase and water solution) of 2-nitroresorcinol, 4, 6-dinitroresorcinol and 2-nitrophenol in their neutral and deprotonated conformations, Chemical physics, 282 (2), pp: 181-195.
[9] Balakrishnan, A., Gaware, G., and Chinthala, M. (2022). Heterojunction photocatalysts for the removal of nitrophenol: A systematic review, Chemosphere, 136853.
[10] Assi, N., Mohammadi, A., Sadr Manuchehri, Q., and Walker, R.B. (2015). Synthesis and characterization of ZnO nanoparticle synthesized by a microwave-assisted combustion method and catalytic activity for the removal of ortho-nitrophenol, Desalination and Water Treatment, 54 (7), pp: 1939-1948.
[11] Zhao, K., Wang, J., Kong, W., and Zhu, P. (2020). Facile Green synthesis and characterization of copper nanoparticles by aconitic acid for catalytic reduction of nitrophenols, Journal of Environmental Chemical Engineering, 8 (2), pp: 103517.
[12] Arasteh, R., Masoumi, M., Rashidi, A.á., Moradi, L., Samimi, V., and Mostafavi, S. (2010). Adsorption of 2-nitrophenol by multi-wall carbon nanotubes from aqueous solutions, Applied Surface Science, 256 (14), pp: 4447-4455.
[13] Pauletto, P., Moreno-Pérez, J., Hernández-Hernández, L., Bonilla-Petriciolet, A., Dotto, G., and Salau, N. (2021). Novel biochar and hydrochar for the adsorption of 2-nitrophenol from aqueous solutions: An approach using the PVSDM model, Chemosphere, 269 128748.
[14] Sellaoui, L., Silva, L.F., Badawi, M., Ali, J., Favarin, N., Dotto, G.L., Erto, A., and Chen, Z. (2021). Adsorption of ketoprofen and 2-nitrophenol on activated carbon prepared from winery wastes: A combined experimental and theoretical study, Journal of Molecular Liquids, 333 115906.
[15] Dalla Nora, F.B., Lima, V.V., Oliveira, M.L., Hosseini-Bandegharaei, A., de Lima Burgo, T.A., Meili, L., and Dotto, G.L. (2020). Adsorptive potential of Zn–Al and Mg–Fe layered double hydroxides for the removal of 2–nitrophenol from aqueous solutions, Journal of Environmental Chemical Engineering, 8 (4), pp: 103913.
[16] Adeosun, W.A., Asiri, A.M., and Marwani, H.M. (2020). Sensitive determination of 2-nitrophenol using electrochemically deposited polymethyl red film for healthcare and environmental safety, Synthetic Metals, 261 116321.
[17] Li, J., He, L., Jiang, J., Xu, Z., Liu, M., Liu, X., Tong, H., Liu, Z., and Qian, D. (2020). Facile syntheses of bimetallic Prussian blue analogues (KxM [Fe (CN) 6]· nH2O, M= Ni, Co, and Mn) for electrochemical determination of toxic 2-nitrophenol, Electrochimica Acta, 353 136579.
[18] Yilmaz, E., Tut, Y., Turkoglu, O., and Soylak, M. (2018). Synthesis and characterization of Pd nanoparticle-modified magnetic Sm2O3–ZrO2 as effective multifunctional catalyst for reduction of 2-nitrophenol and degradation of organic dyes, Journal of the Iranian Chemical Society, 15 (8), pp: 1721-1731.
[19] Rebaz, O., KOPARIR, P., QADER, I., and AHMED, L.J.G.U.J.o.S. (2022). Theoretical Determination of Corrosion Inhibitor Activities of Naphthalene and Tetralin, 1-1.
[20] QADER, İ.N., MOHAMMAD, A., AZEEZ, Y.H., AGİD, R.S., HASSAN, H.S., AL-NABAWİ, S.H.M.J.J.o.P.C., and Materials, F. Chemical Structural and Vibrational Analysis of Potassium Acetate: A Density Function Theory Study, 2 (1), pp: 23-25.
[21] Pearson, R.G.J.I.c. (1988). Absolute electronegativity and hardness: application to inorganic chemistry, 27 (4), pp: 734-740.
[22] Aydoğmuş, Z., Aslan, S.S., Yildiz, G., and Senocak, A.J.J.o.a.c. (2020). Differential Pulse Voltammetric Determination of Anticancer Drug Regorafenib at a Carbon Paste Electrode: Electrochemical Study and Density Functional Theory Computations, 75 (5), pp: 691-700.
[23] AHMED, L., Rebaz, O.J.J.o.P.C., and Materials, F. (2019). A theoretical study on Dopamine molecule, 2 (2), pp: 66-72.
[24] Bálint, D. and Jäntschi, L.J.M. (2021). Comparison of molecular geometry optimization methods based on molecular descriptors, 9 (22), pp: 2855.
[25] AKTAŞ, A.E., Rebaz, O., KOPARIR, M.J.J.o.P.C., and Materials, F. Synthesis, Characterization and Theoretical Anti-Corrosion Study for Substitute Thiazole Contained Cyclobutane Ring, 5 (1), pp: 111-120.
[26] Plakhutin, B.N. and Davidson, E.R.J.T.J.o.P.C.A. (2009). Koopmans’ theorem in the restricted open-shell Hartree− Fock Method. 1. A variational approach, 113 (45), pp: 12386-12395.
[27] Koopmans, T.J.p. (1934). Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den einzelnen Elektronen eines Atoms, 1 (1-6), pp: 104-113.
[28] Shahab, H., Husain, Y.J.P.J.o.B., and Sciences, A. (2021). Theoretical Study for Chemical Reactivity Descriptors of Tetrathiafulvalene in gas phase and solvent phases based on Density Functional Theory, 3 (2), pp: 167-173.
[29] Kiyooka, S.-i., Kaneno, D., and Fujiyama, R.J.T.L. (2013). Parr’s index to describe both electrophilicity and nucleophilicity, 54 (4), pp: 339-342.
[30] Ernst, H.A., Wolf, T.J., Schalk, O., González-García, N., Boguslavskiy, A.E., Stolow, A., Olzmann, M., and Unterreiner, A.-N.J.T.J.o.P.C.A. (2015). Ultrafast dynamics of o-nitrophenol: An experimental and theoretical study, 119 (35), pp: 9225-9235.
[31] Nasidi, I.I., Kaygili, O., Majid, A., Bulut, N., Alkhedher, M., and ElDin, S.M.J.A.O. (2022). Halogen Doping to Control the Band Gap of Ascorbic Acid: A Theoretical Study.
[32] Kareem, R.O., Kaygili, O., Ates, T., Bulut, N., Koytepe, S., Kuruçay, A., Ercan, F., and Ercan, I.J.C.I. (2022). Experimental and theoretical characterization of Bi-based hydroxyapatites doped with Ce, 48 (22), pp: 33440-33454.
[33] Korkmaz, A.A., Ahmed, L.O., Kareem, R.O., Kebiroglu, H., Ates, T., Bulut, N., Kaygili, O., and Ates, B.J.J.o.t.A.C.S. (2022). Theoretical and experimental characterization of Sn-based hydroxyapatites doped with Bi, 1-13.
[34] Hssain, A.H., Bulut, N., Ates, T., Koytepe, S., Kuruçay, A., Kebiroglu, H., and Kaygili, O.J.C.P.L. (2022). The experimental and theoretical investigation of Sm/Mg co-doped hydroxyapatites, 800 139677.
[35] Mahmood, B.K., Kaygili, O., Bulut, N., Dorozhkin, S.V., Ates, T., Koytepe, S., Gürses, C., Ercan, F., Kebiroglu, H., and Agid, R.S.J.C.I. (2020). Effects of strontium-erbium co-doping on the structural properties of hydroxyapatite: An Experimental and theoretical study, 46 (10), pp: 16354-16363.
[36] Edwards, A.A. and Alexander, B.D. (2017). UV-Visible absorption spectroscopy, organic applications.
[37] Wu, T.-Y.J.P.R. (1955). Electron affinity of boron, carbon, nitrogen, and oxygen atoms, 100 (4), pp: 1195.
[38] Zhelavskaya, I.S., Shprits, Y.Y., and Spasojevic, M., Reconstruction of plasma electron density from satellite measurements via artificial neural networks, in Machine learning techniques for space weather2018, Elsevier. p. 301-327.
[39] Bort, J.A. and Rusca, J.B., (2007). Theoretical and computational chemistry: foundations, methods and techniques, Publicacions de la Universitat Jaume I,
[40] Yu, F., Li, J., Liu, Z., Wang, R., Zhu, Y., Huang, W., Liu, Z., and Wang, Z.J.J.o.C.S. (2022). From Atomic Physics to Superatomic Physics, 1-18.