Molecular Structure, Thermochemistry, Non-Covalent Interactions Computation Using DFT Studies Of The 1 Amino 2-(3,4- Dihydroxyphenyl) Boronic Acid (AHPEBA) Compound

Year 2024, Volume: 7 Issue: 1, 1 - 10, 03.06.2024

Rebaz Obaıd Kareem

https://doi.org/10.54565/jphcfum.1395735

Cited By: 2

Abstract

Theoretical parameters for 1 amino 2-(3,4- dihydroxyphenyl) boronic acid in AHPEBA were investigated using density functional theory (DFT), and STO-3G basis set. Quantum chemical calculations were done on the link between inhibitor molecular structure, chemical reactivity, stability, and inhibition performance. In addition, we investigate the theoretical foundations of AHPEBA by looking at properties and characteristics such as the Highest Occupied Molecular Orbital (HOMO), the Lowest Unoccupied Molecular Orbital (LUMO), the Band Gap (BG), the Density of States (DOS), the Ultraviolet (UV) properties, and the Natural Bond Orbital (NBO) evaluations. Also, we use the reduced density gradient (RDG) method to explore non-covalent interactions (NCI). The fact that the BG was measured to be -5.85043 eV lent credence to the hypothesis that the molecule had a high level of chemical stability and a low level of chemical reactivity. According to molecular hardness and softness, electronegativity, and chemical potential, the molecule C8H12BNO4 has a high degree of chemical stability, and a low degree of reactivity. This is the first theoretical study of the AHPEBA compound.

Keywords

NCI, RDG, FTIR, UV, Thermochemistry, HOMO-LUMO, AHPEBA compound

References

• Ueno, H., Iwata, T., Koshiba, N., Takahashi, D. And Toshima, K., 2013. Design, Synthesis And Evaluation Of A Boronic Acid Based Artificial Receptor For L-DOPA In Aqueous Media. Chemical Communications, 49(88), Pp.10403-10405.
• Enquiry. (2005).(1-Amino-2-(3,4-Dihydroxyphenyl)Ethyl)Boronic Acid ,95% Min., Hairui Chemical.
• Pantalone, S., 2022. Food Contaminants Due To Thermal Process.
• Du, J., He, M., Wang, X., Fan, H. And Wei, Y., 2015. Facile Preparation Of Boronic Acid‐Functionalized Magnetic Nanoparticles With A High Capacity And Their Use In The Enrichment Of Cis‐Diol‐Containing Compounds From Plasma. Biomedical Chromatography, 29(2), Pp.312-320.
• Chouchou, A., Patinote, C., Cuq, P., Bonnet, P.A. And Deleuze-Masquéfa, C., 2018. Imidazo [1, 2-A] Quinoxalines Derivatives Grafted With Amino Acids: Synthesis And Evaluation On A375 Melanoma Cells. Molecules, 23(11), P.2987.
• Cross-Coupling, I. And Boronates, M.I.D.A., MIDA-Protected Boronate Esters.
• Venkatesh, G. And Singh, A.K., 2005. 2-{[1-(3, 4-Dihydroxyphenyl) Methylidene] Amino} Benzoic Acid Immobilized Amberlite XAD-16 As Metal Extractant. Talanta, 67(1), Pp.187-194.
• Lin, N., Yan, J., Huang, Z., Altier, C., Li, M., Carrasco, N., Suyemoto, M., Johnston, L., Wang, S., Wang, Q. And Fang, H., 2007. Design And Synthesis Of Boronic-Acid-Labeled Thymidine Triphosphate For Incorporation Into DNA. Nucleic Acids Research, 35(4), Pp.1222-1229.
• Whyte, G.F., Vilar, R. And Woscholski, R., 2013. Molecular Recognition With Boronic Acids—Applications In Chemical Biology. Journal Of Chemical Biology, 6, Pp.161-174. Ferreira, O.O., Mali, S.N., Jadhav, B., Chtita, S., Kuznetsov, A., Bhandare, R.R., Shaik, A.B., Siddique, F., Yadav, A.R., Lai, C.H. And Cruz, J.N., 2023. Synthesis, In-Silico, In Vitro And DFT Assessments Of Substituted Imidazopyridine Derivatives As Potential Antimalarials Targeting Hemoglobin Degradation Pathway. Journal Of Computational Biophysics And Chemistry, 22(7), Pp.795-814.
• Rhazi, Y., Chalkha, M., Nakkabi, A., Hammoudan, I., Akhazzane, M., Bakhouch, M., Chtita, S. And El Yazidi, M., 2022. Novel Quinazolinone–Isoxazoline Hybrids: Synthesis, Spectroscopic Characterization, And DFT Mechanistic Study. Chemistry, 4(3), Pp.969-982.
• Hammoudan, I., Chtita, S. And Riffi-Temsamani, D., 2020. QTAIM And IRC Studies For The Evaluation Of Activation Energy On The C= P, C= N And C= O Diels-Alder Reaction. Heliyon, 6(8).
• HAMAD, O., KAREEM, R.O. And Kaygili, O., 2023. Density Function Theory Study Of The Physicochemical Characteristics Of 2-Nitrophenol. Journal Of Physical Chemistry And Functional Materials, 6(1), Pp.70-76.
• Koohi, M. And Bastami, H., 2023. Investigation Of Ti—B Nanoheterofullerenes Evolved From C20 Nanocage Through DFT. Chemical Review And Letters, 6(2), Pp.223-234.
• Azeez, Y.H., Kareem, R.O., Qader, A.F., Omer, R.A. And Ahmed, L.O., 2024. Spectroscopic Characteristics, Stability, Reactivity, And Corrosion Inhibition Of AHPE-Dop Compounds Incorporating (B, Fe, Ga, Ti): A DFT Investigation.
• Rasul, H.H., Mamad, D.M., Azeez, Y.H., Omer, R.A. And Omer, K.A., 2023. Theoretical Investigation On Corrosion Inhibition Efficiency Of Some Amino Acid Compounds. Computational And Theoretical Chemistry, P.114177.
• El Idrissi, M., Elharfaoui, S., Zmirli, Z., Mouhssine, A., Dani, A., Salle, B., Tounsi, A., Digua, K., And Chaair, H. (2024). Theoretical And Experimental Study Of The Orientation To The Most Effective Coagulant For Removing Reactive Black-5 Dye From Industrial Effluents, Physical Chemistry Research, 12 (1), Pp: 229-248.
• Mamand, D.M., Azeez, Y.H. And Qadr, H.M., 2023. Monte Carlo And DFT Calculations On The Corrosion Inhibition Efficiency Of Some Benzimide Molecules. Mongolian Journal Of Chemistry, 24(50), Pp.Xx-Xx.
• Hussein, Y.T. And Azeez, Y.H., 2023. DFT Analysis And In Silico Exploration Of Drug-Likeness, Toxicity Prediction, Bioactivity Score, And Chemical Reactivity Properties Of The Urolithins. Journal Of Biomolecular Structure And Dynamics, 41(4), Pp.1168-1177.
• Kebiroglu, H., Hamad, O.A., Kaygili, O. And Bulut, N., Epinephrine Compound: Unveiling Its Optical And Thermochemical Properties Via Quantum Computation Methods.
• Verma, P., Janesko, B.G., Wang, Y., He, X., Scalmani, G., Frisch, M.J., And Truhlar, D.G. (2019). M11plus: A Range-Separated Hybrid Meta Functional With Both Local And Rung-3.5 Correlation Terms And High Across-The-Board Accuracy For Chemical Applications, Journal Of Chemical Theory And Computation, 15 (9), Pp: 4804-4815.
• Sucheta, M., Pramod, A.G., Zikriya, M., Salma, K.M., Venugopal, N., Chaithra, R., Harshitha, D., Amudan, S., Renuka, C.G. And Murthy, S., 2022. Frontier Molecular Orbital, Molecular Structure And Thermal Properties Of 2, 4, 6, 8-Tetramethyl-2, 3, 6, 7-Tetrahydro-S-Indacene-1, 5-Dione Using DFT Calculation. Materials Today: Proceedings, 62, Pp.5241-5244.
• O'boyle, N.M., Tenderholt, A.L. And Langner, K.M., 2008. Cclib: A Library For Package‐Independent Computational Chemistry Algorithms. Journal Of Computational Chemistry, 29(5), Pp.839-845.
• Mohamed, H.S.H. And Ahmed, S.A., 2019. Reviewing Of Synthesis And Computational Studies Of Pyrazolo Pyrimidine Derivatives. J Chem Rev, 1(3), Pp.154-251.
• Hammoudan, I., Aboulmouhajir, A., Dakir, M., Temsamani, D.R., Bakhouch, M., Bazi, D.E. And Chtita, S., 2023. Mechanistic Elucidation Of Diels–Alder Cycloaddition Reactions Between Quinoflavonoid And Substituted Butadiene Using LOL, ELF, QTAIM, And DFT Studies. Structural Chemistry, 34(3), Pp.959-969.
• Johnson, E.R., Keinan, S., Mori-Sánchez, P., Contreras-García, J., Cohen, A.J. And Yang, W., 2010. Revealing Noncovalent Interactions. Journal Of The American Chemical Society, 132(18), Pp.6498-6506.
• Akman, F., Demirpolat, A., Kazachenko, A.S., Kazachenko, A.S., Issaoui, N. And Al-Dossary, O., 2023. Molecular Structure, Electronic Properties, Reactivity (ELF, LOL, And Fukui), And NCI-RDG Studies Of The Binary Mixture Of Water And Essential Oil Of Phlomis Bruguieri. Molecules, 28(6), P.2684.
• Domingo, L.R., Aurell, M.J., Pérez, P. And Contreras, R., 2002. Quantitative Characterization Of The Global Electrophilicity Power Of Common Diene/Dienophile Pairs In Diels–Alder Reactions. Tetrahedron, 58(22), Pp.4417-4423.
• Macbride, D.M., Malone, C.G., Hebb, J.P. And Cravalho, E.G., 1997. Effect Of Temperature Variation On FT-IR Spectrometer Stability. Applied Spectroscopy, 51(1), Pp.43-50.
• Ikawa, T., Simple Arylation, In Comprehensive Aryne Synthetic Chemistry2022, Elsevier. P. 15-56.
• Speight, J.G., 2016. Environmental Organic Chemistry For Engineers. Butterworth-Heinemann.
• Gupta, V., (2015). Principles And Applications Of Quantum Chemistry, Academic Press,
• Ouellette, R.J. And Rawn, J.D., (2015). Principles Of Organic Chemistry, Academic Press,
• MAMAND, D., 2019. Theoretical Calculations And Spectroscopic Analysis Of Gaussian Computational Examination-NMR, FTIR, UV-Visible, MEP On 2, 4, 6-Nitrophenol. Journal Of Physical Chemistry And Functional Materials, 2(2), Pp.77-86.
• Croker, E.L. And Basu-Dutt, S., 2002. A Classical And Quantum Chemical Analysis Of Gaseous Heat Capacity. The Chemical Educator, 7(3), Pp.136-141.
• Vijjapu, R. And Tiwari, S., 2022. Thermodynamics Of Sensible Thermal Energy Storage Systems.
• López-Chávez, E., Cruz-Torres, A., De Landa Castillo-Alvarado, F., Ortíz-López, J., Peña-Castañeda, Y.A. And Martínez-Magadán, J.M., 2011. Vibrational Analysis And Thermodynamic Properties Of C 120 Nanotorus: A DFT Study. Journal Of Nanoparticle Research, 13, Pp.6649-6659.
• Parlak, A.E., Omar, R.A., Koparir, P. And Salih, M.I., 2022. Experimental, DFT And Theoretical Corrosion Study For 4-(((4-Ethyl-5-(Thiophen-2-Yl)-4H-1, 2, 4-Triazole-3-Yl) Thio) Methyl)-7, 8-Dimethyl-2H-Chromen-2-One. Arabian Journal Of Chemistry, 15(9), P.104088.
• Korkmaz, A.A., Ahmed, L.O., Kareem, R.O., Kebiroglu, H., Ates, T., Bulut, N., Kaygili, O. And Ates, B., 2022. Theoretical And Experimental Characterization Of Sn-Based Hydroxyapatites Doped With Bi. Journal Of The Australian Ceramic Society, 58(3), Pp.803-815.
• Kareem, R.O., Kaygili, O., Ates, T., Bulut, N., Koytepe, S., Kuruçay, A., Ercan, F. And Ercan, I., 2022. Experimental And Theoretical Characterization Of Bi-Based Hydroxyapatites Doped With Ce. Ceramics International, 48(22), Pp.33440-33454.
• İsen, F., Kaygili, O., Bulut, N., Ates, T., Osmanlıoğlu, F., Keser, S., Tatar, B., Özcan, İ., Ates, B., Ercan, F. And Ercan, I., 2023. Experimental And Theoretical Characterization Of Dy-Doped Hydroxyapatites. Journal Of The Australian Ceramic Society, Pp.1-16.
• Kareem, R.O., 2023. Synthesis And Characterization Of Bismuth-Based Hydroxyapatites Doped With Cerium.
• Kamel, M. And Mohammadifard, K., 2021. Thermodynamic And Reactivity Descriptors Studies On The Interaction Of Flutamide Anticancer Drug With Nucleobases: A Computational View. Chemical Review And Letters, 4(1), Pp.54-65.
• Kareem, R.O., Kebiroğlu, M.H., Hamad, O.A., Kaygili, O. And Bulut, N., Epinephrine Compound: Unveiling Its Optical And Thermochemical Properties Via Quantum Computation Methods 2024.
• Shahab, H. And Husain, Y., 2021. Theoretical Study For Chemical Reactivity Descriptors Of Tetrathiafulvalene In Gas Phase And Solvent Phases Based On Density Functional Theory. Passer Journal Of Basic And Applied Sciences, 3(2), Pp.167-173.
• Mustafa, M.D. And Mohammad, Q.H., 2023. Quantum Chemical And Monte Carlo Simulations On Corrosion Inhibition Efficiency Of 2-Mercapto-5-Phenylfuran And Bis (Pyridyl) Oxadiazoles. Известия Высших Учебных Заведений. Химия И Химическая Технология, 66(8), Pp.33-45.