Molecular Geometry, Homo-Lumo Analysis and Mulliken Charge Distribution of 2,6-Dichloro-4-Fluoro Phenol Using DFT and HF Method
Phenolic compounds are used in human diet, commonly present in plants. Foremost polyphenolic compounds found in plants are flavanols, flavonoids, flavonones, iso-flavones, phenolic acids, flavonoids, chalcones, lignans etc. These compounds possess antimicrobial, antiviral and anti-inflammatory properties along with high antioxidative activity. The antioxidative activity of phenolic compounds depends on their structure. The polyphenols are very useful for the treatment of inflammation, cancer, anti-ageing purposes in cosmetic formulations, and nutraceutical applications. This article focused on substituted phenol, taking into concern their potential health benefits. The recent rise in machine-learning methods has engendered many advances in the molecular sciences. Using desired level of electronic structure theory from density functional theory, we can calculate the properties (electronic structure, force field, energy) of atomistic systems. The full electron density carries with it a considerable computational cost. While the DFT calculation loses accuracy when the molecule is either extended or compressed, Δ-DFT corrects these errors. Here, molecular point group symmetries are used to obtain chemical accuracy. The optimal 2,6-dichloro-4-fluoro phenol molecular geometry was derived using the 6-311+G (d, p) basis set and DFT/B3LYP (density functional theory) and Hartree-Fock (HF) techniques. A detailed interpretation of Homo-Lumo analysis of 2,6-dichloro-4-fluoro phenol is also listed. Using the 6-311+G (d, p) basis set and the Hartree-Fock (HF) method, the Mulliken charge distribution of this molecule has also been computed.
R.A. Yadav, P. Rani, M. Kumar, R. Singh, P. Singh, and N.P. Singh, “Experimental IR and Raman spectra & quantum chemical studies of molecular structures, conformers & vibrational characteristics of L-ascorbic acid”, Spectrochemica Acta A, 84(1), 6 (2011). https://doi.org/10.1016/j.saa.2011.07.043
V. Krishnakumar et al., “Vibrational and normal coordinate analysis of xanthine and hypoxanthine”, Indian J. of Physics, 42(06), 411-418 (2004). http://nopr.niscpr.res.in/handle/123456789/26125
V.K. Rastogi, V. Jain, M.A. Palafox, D.N. Singh, and R.A. Yadav, “The variation of enthalpy function and heat capacity of 2,6,4 DCFP”, Spectrochemica Acta, 57(A), 209 (2001). https://doi.org/10.1016/S1386-1425(00)00327-9
V. Krishnakumar, and V. Balachandran, “FTIR, FT-Raman spectral analysis and normal coordinate calculations of 2-hydroxy-3-methoxy-benzyldehyde-thio-semicarbozone”, Indian J. of Pure and Appl. Physics, 42, 313-318 (2004). http://nopr.niscpr.res.in/bitstream/123456789/9583/1/IJPAP%2042%285%29%20313-318.pdf
S. Gunasekaran, and P. Abitha, Indian J. of Pure and Appl. Physics, 43, 329-334 (2005). http://nopr.niscpr.res.in/bitstream/123456789/8791/1/IJPAP%2043%285%29%20329-334.pdf
S. Chaudhary, Ph. D. Thesis, “Spectral investigation and thermodynamic functions of some aromatic molecules”, C.C.S Univ. 2001.
V. Krishnakumar, and R.J. Xavier, “FT-Raman and FT-IR spectral studies of 3-mercapto-1,2,4 triazole”, Indian J. of Pure and Appl. Phys. 41, 95-112 (2003). http://nopr.niscpr.res.in/bitstream/123456789/25035/1/IJPAP%2041%282%29%2095-99.pdf
Fu. Aiping, Du. Dongmei, and Z. Zhengyu, “Study of formamide-meyhonal dimer with ab initio and density function theory methods”, Journal of Quantum Chemistry, 97, 865-875 (2004). https://doi.org/10.1002/qua.10796
A. Altum, K. Gölcük, and M. Kumru, Journal of Molecular Structure, 637, 155 (2003). https://doi.org/10.1016/S0166-1280(03)00531-1
V. Krishnakumar, and R. Ramasamy, “Spectral and normal coordinate analysis of 6-methoxy purine”, Indian J. of Pure and App. Physics, 40, 252-255 (2002). https://www.researchgate.net/publication/279895257_Spectral_and_normal_coordinate_analysis_of_6-methoxy_purine
B.S. Yadav et al., “FT-IR spectroscopic studies of 2-hydroxy-4-methyl pyrimidine hydrochloride” Asain journal of chemistry, 20(1), 273-276 (2008).https://asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=20_1_43
V. Krishnakumar et al., “Normal coordinate analysis of vibrational spectra of 2- methyliodine and 5-hysdroxyinolane”, Indian J. of Pure and Appl. Physics, 41, 85-99 (2003). https://www.semanticscholar.org/paper/Normal-coordinate-analysis-of-vibrational-spectra-Krishnakumar-Xavier/bb1c9858cca12a0d182404e34ec3db17af178eb8
R.L. Frost, Y. Xi, S.J. Palmer, G.J. Millar, K. Tan, and R.E. Pogson, “Vibrational spectroscopy of synthetic stecorite H(NH4)Na(PO4)·4H2O”, Spectrochimica Acta A, 84(1), 269-274 (2011). https://doi.org/10.1016/j.saa.2011.09.040
M. Karabacak, M. Cinar, Z. Unal, and M. Kurt, “Spectroscopic and computational studies on 3-methyl aniline”, Mol. Struct. 982, 22-27 (2010). https://doi.org/10.1016/j.molstruc.2010.07.033
V.P. Gupta, and P. Tandon, “Conformational and vibrational studies of isomeric hydrogen cynide tetramers by quantum chemical methods”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 89, 55-66 (2012). https://doi.org/10.1016/j.saa.2011.12.030
M.J. Frisch et al., Gaussian 09 Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
A. Abhas et al., Spectrochimica Acta Part A, 21, 376-383 (2015). https://doi.org/10.1016/j.saa.2014.11.024
Samuel Tetteh et al, Electronic Spectra of ortho-Substituted Phenols: An Experimental and DFT Study”, Hindawi Journal of Spectroscopy, 1, 1-10 (2018). https://doi.org/10.1155/2018/4193657
F.A. Pasha, H.K. Srivastava, Y. Beg, and P.P. Singh, “DFT Based Electrophilicity Index and QSAR study of Phenols as Anti Leukaemia Agent”, American Journal of Immunology, 2(1), 23-28 (2006). https://thescipub.com/pdf/ajisp.2006.23.28.pdf
M. Bogojeski, L. Vogt-Maranto, M.E. Tuckerman, K.-R. Müller, and K. Burke, “Quantum chemical accuracy from density functional approximations via machine learning”, Nature Communication, 11, 5223 (2020). https://doi.org/10.1038/s41467-020-19093-1
J. Teotia et al., “Ultraviolet Absorption Spectra, Solvent Effect and Non-Linear Optical Properties of 2-Amino-4,6 dimethylpyridine by Hartee-Fock and Density Functional Theory”, Asian Journal of Chemistry, 28(10), 2204-2210 (2016). https://doi.org/10.14233/ajchem.2016.19928
S. Kumar, R. Kumar, J. Teotia, and M.K. Yadav, “Experimental & theoritical (ab initio & DFT) analysis of UV-Vis spectra, thermodynamic functions & nonlinear optical properties of 2-chloro-3,4-dimethylbenzyl dehyde”, Journal of Advances in Physics, 8(2), 2122-2134 (2015). https://rajpub.com/index.php/jap/article/view/1519/pdf_158
S. Kumar, Surbhi, and M.K. Yadav, “Optimized Molecular Geometries, Internal Coordinates, Vibrational Analysis, Thermodynamic properties, First Hyper Polarizability and Homo-Lumo Analysis of Duroquinone using Density Functional Theory and Hartree-Fock Method.”, Russian Journal of Physical Chemistry B, 15, S22–S31 (2021). https://doi.org/10.1134/S1990793121090116
H. Kumar, N. Choudhary, Varsha, N. Kumar, Suman, and R. Seth, “Phenolic compounds and their health benefits: A review”, Journal of Food Research and Technology April-June, 2(2), 46-59 (2014). https://www.researchgate.net/profile/Harish-Kumar-96/publication/350966390_Phenolic_compounds_and_their_health_benefits_A_review/links/607d535b8ea909241e0cf38c/Phenolic-compounds-and-their-health-benefits-A-review.pdf
X. Xiang, Z.-X. Zhao, and H.-X. Zhang, “A theoretical study based on DFT calculations on the different influence of functional groups on the C–H activation process via Pd-catalysed β-X elimination”, Royal Society of Chemistry, 12, 26116-26122 (2022). https://doi.org/10.1039/D2RA03506E
S. Bhandari, R. Khatun, T.S. Khan, D. Khurana, M.K. Poddar, A. Shukla, V.V.D.N. Prasada, and R. Bal, “Preparation of a nanostructured iron chromite spinel in the pure form and its catalytic activity for the selective oxidation of benzene to phenol: experimental and DFT studies”, Journal of Green Chemistry, 24, 9303-9314 (2022). https://doi.org/10.1039/D2GC02335K
F. Maldonado, L. Villamagua, and R. Rivera “DFT Analysis of the Adsorption of Phenol on the Nonpolar (101̅0) ZnO Surface”, J. Phys. Chem. C, 123(19), 12296–12304 (2019). https://doi.org/10.1021/acs.jpcc.9b01906
Sarvendra et al., “Vibrational spectroscopic investigation, first hyper polarizability & Homo Lumo analysis of tetrahydroxy-1,4 quinone hydrate using DFT and HF methods”, Russian J. of Physical Chemistry B, 12(3), 383-393 (2018).
Seema et al., “Ultraviolet absorption spectra, solvent effect and Non- linear Optical properties of 1,2,4,5-tetrachloro-3-nitrobenzene by hartee-fock density functional theory” International journal of research and analytical reviews, 6(2), 2241-2248 (2019). http://ijrar.org/viewfull.php?&p_id=IJRAR19K3768
S. Kumar, Surbhi, and M.K. Yadaw, S. Kumar, Surbhi, and M.K. Yadaw, “Ultraviolet Absorption spectra, solvent effect and non-linear optical properties of tetrahydroxy-1-4 quinone hydrate by HF and DFT theory”, Asian Journal of Chemistry, 29(10), 2241-2248 (2017). https://doi.org/10.14233/ajchem.2017.20741
Copyright (c) 2023 Surbhi, Deeya Shalya, Sarvendra Kumar
This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).