The Computational Investigation of IR and UV-Vis Spectra of 2-isopropyl-5-methyl-1,4-benzoquinone Using DFT and HF Methods
A theoretical study on the thymoquinone compound has been performed through two theoretical methods, DFT/B3LYP and HF with 6-31G, 6-31G(d, p) and 6-31++G(d, p) basis sets using Gaussian 09 program. Some theoretical properties, like vibrational and electronic properties especially UV-Vis and FT-IR spectra, of the title compound were analyzed and then compared with available experimental data. The calculated harmonic vibrational frequencies have been scaled with standard scaling factors 0.9 and 0.965 for HF and DFT/B3LYP, respectively and then compared with available experimental FT-IR spectrum. Furthermore, the statistical analysis was investigated to evaluate the performance of both the HF and DFT methods, including root mean square error (RMSE), mean absolute error (MAE) and mean percentage error (MPE). According to the assigned vibrational modes of the title compound, it could be concluded that the DFT/B3LYP method with 6-31++G(d, p) basis set had the best agreement with experimental data. UV-Vis absorption spectra, excitation energies, maximum absorption wavelength, electronic transitions and oscillator strengths of the title compound were calculated by time dependent density functional theory ( TD-DFT) method using the same basis set and compared with available experimental data. The results showed the best performer was HF method with 6-31G basis set.
B.H. Ali, and G. Blunden, “Pharmacological and toxicological properties of Nigella sativa”, Phytother. Res. 17, 299-305 (2003). https://doi.org/10.1002/ptr.1309
Z. Erisgin, M. Atasever, K. Cetinkaya, S.A. Dizakar, S. Omeroglu, and H. Sahin, “Protective effects of, Nigella sativa oil against carboplatin-induced liver damage in rats”, Biomedicine & Pharmacotherapy, 110, 742-747 (2019). https://doi.org/10.1016/j.biopha.2018.12.037
P.K. Perera, D.T. Karunaratne, and N. Kalka, Antiinflammatory Actions and Potential Usage for Arthritic Conditions, Bioactive Food as Dietary Interventions for Arthritis and Related Inflammatory Diseases, (2nd edition), (Academic Press, 2019), pp. 323-341. https://doi.org/10.1016/B978-0-12-813820-5.00019-2
M. El-Dakhakhny, “Studies on the Egyptian Nigella sativa L. IV. Some pharmacological properties of the seeds’ active principle in comparison to its dihydro compound and its polymer”, Arzneimittel-forsch, 15(10), 1227–1229 (1965).
M.E. Abd El-Hack, M. Alagawany, M.R. Farag, R. Tiwari, K. Karthik, and K. Dhama, “Nutritional, Healthical and Therapeutic Efficacy of Black Cumin (Nigella sativa) in Animals, Poultry and Humans”, International Journal of Pharmacology, 12, 232-248 (2016). https://doi.org/10.3923/ijp.2016.232.248
H. Mollazadeh, A.R. Afshari, and H. Hosseinzadeh, “Review on the Potential Therapeutic Roles of Nigella sativa in the Treatment of Patients with Cancer: Involvement of Apoptosis: Black cumin and cancer”, J. Pharmacopuncture, 20(3), 158-172 (2017). https://doi.org/10.3831%2FKPI.2017.20.019
M.A. Randhawa, M. Al-Ghamdi, M. Al-Ghamdi, “Anticancer Activity of Nigella sativa (Black Seed) - A Review”, The American Journal of Chinese Medicine, 39(6), 1075 (2011). https://doi.org/10.1142/S0192415X1100941X
D.R. Worthen, O.A. Ghosheh, P.A. Crooks, “The in vitro anti-tumor activity of some crude and purified components of blackseed, Nigella sativa L”, Anticancer Res. 18, 1527-1532 (1998).
M. Burits, F. Bucar, “Antioxidant activity of Nigella sativa essential oil”, Phytotherapy Research, 14, 323-328 (2000). https://doi.org/10.1002/1099-1573(200008)14:5%3C323::AID-PTR621%3E3.0.CO;2-Q
P.J. Houghton, R. Zarka, B. de la Heras, J.R.S. Hoult, “Fixed oil of Nigella sativa and derived thymoquinone inhibit eicosanoid generation in leukocytes and membrane lipid peroxidation”, Planta Medica, 61, 33-36 (1995). https://doi.org/10.1055/s-2006-957994
N.M. Morsi, “Antimicrobial effect of crude extracts of Nigella sativa on multiple antibiotics-resistant bacteria”, Acta Microbiologica Polonica, 49, 63-74 (2000).
M.L. Salem, and M.S. Hossain, “In vivo acute depletion of CD8(+) T cells before murine cytomegalovirus infection upregulated innate antiviral activity of natural killer cells”, International Journal of Immunopharmacology, 22, 707-718 (2000). https://doi.org/10.1016/S0192-0561(00)00033-3
A.H. Gilani, N. Aziz, I.M. Khurram, K.S. Chaudhary, A. Iqbal, “Bron-chodilator.“Spasmolytic and Calcium Antagonist Activities of Nigella sativa seeds (Kalonji): a traditional herbal product with Multiple Me-dicinal Uses”, J. Pak. Med. Assoc. 51, 115-119 (2001). https://ecommons.aku.edu/pakistan_fhs_mc_bbs/422
M.S. Iqbal, A. Jafri, Md. Arshadb, and M.I. Ansari, “Stress response due to sodium azide treatment inside Nigella sativa L. plant and its effect on antioxidative property”, Biocatalysis and Agricultural Biotechnology, 19, 101171 (2019). https://doi.org/10.1016/j.bcab.2019.101171
C. Moller, and M.S. Plesset,“Note on an Approximation Treatment for Many-Electron Systems”, Phys. Rev. 46, 618–622 (1934). https://doi.org/10.1103/PhysRev.46.618
A.D. Becke, “Density-Functional Exchange-Energy Approximation with Correct Asymptotic-Behavior”, Phys. Rev. A, 38(6), 3098–3100 (1988). https://doi.org/10.1103/PhysRevA.38.3098
C.T. Lee, W.T. Yang, and R.G. Parr, “Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron-Density”, Phys. Rev. B, 37(2), 785–789 (1988). https://doi.org/10.1103/PhysRevB.37.785
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, et al, Gaussian 03, Revision C.02, (Gaussian, Inc, Wallingford CT, 2004).
R. Denning, T. Keith, J. Millam, K. Eppinnett, W. Hovell, and R.G. Gilliland, Version 3.09, (Semichem. Inc., Shawnee Mission, KS, 2003).
M.A. Palafox, “DFT computations on vibrational spectra: Scaling procedures to improve the wavenumbers”, Physical Sciences Reviews, 3(6), 20170184 (2018). https://doi.org/10.1515/psr-2017-0184
Integrated Spectral Data Base System for Organic Compounds, (Ibaraki, Japan, National Institute of Advanced In-dustrial Science and Technology, 2003).
Y. Yamakita, and M. Tasumi, “Vibrational analyses of p-benzoquinodimethane and p-benzoquinone based on ab initio Hartree-Fock and second-order Moller-Plessetcalculations”, J. Phys. Chem. 99, 8524-8534(1995). https://doi.org/10.1021/j100021a013
R. Gupta, “Study of spectral and NLO properties of 2-methyl-5-(Propan-2-yl) phenol by DFT”, IJSRED, 4(3), 689-705 (2021). http://www.ijsred.com/volume4/issue3/IJSRED-V4I3P94.pdf
K.M. Marzec, I. Reva, R. Fausto, and L.M. Proniewicz, “Comparative Matrix Isolation Infrared Specroscopy Study of 1,3- and 1,4- DieneMonoterpenes (α- Phellandrene and γ-Terpinene)”, J. Phys. Chem. A, 115, 4342-4353 (2011). https://doi.org/10.1021/jp2013122
R. Abu-Dahab, F. Odeh, S.I. Ismail, H. Azzam, and A. Al Bawab, “Preparation, characterization and antiproliferative activity of thymoquinone-β-cyclodextrin self-assembling nanoparticles”, Pharmazie, 68, 939–944 (2013). https://doi.org/10.1691/ph.2013.3033
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