The prediction of pKa values for phenolic compounds by the DFT theory
Tóm tắt: 107
| 
PDF: 59 
##plugins.themes.academic_pro.article.main##
Author
Từ khóa:
Tóm tắt
The acid dissociation constant is an important parameter that affects the physicochemical properties of molecules in solution. A set of 20 phenolic compounds were used to establish a model to predict values of phenolic compounds. Calculations in aqueous medium were performed with a polarizable continuum solvent model (PCM) and three hybrid DFT functionals (B3LYP, PBE0, ωB97XD and M062X) with the basis set 6-311++G(d,p). The directly calculated value of gives less accurate results with an average absolute error (MAE) of 1.74 units when using the ωB97XD functional and phenol as reference compound. In the case of using statistical correction, the accuracy of is greatly improved. In the case of using statistical correction, the accuracy of is greatly improved with the lowest MAE value of 0.14 units (M062X; ). The calculated results of in this study have the same accuracy as the experimental measurements.The acid dissociation constant is an important parameter that affects the physicochemical properties of molecules in solution. A set of 20 phenolic compounds were used to establish a model to predict values of phenolic compounds. Calculations in aqueous medium were performed with a polarizable continuum solvent model (PCM) and three hybrid DFT functionals (B3LYP, PBE0, ωB97XD and M062X) with the basis set 6-311++G(d,p). The directly calculated value of gives less accurate results with an average absolute error (MAE) of 1.74 units when using the ωB97XD functional and phenol as reference compound. In the case of using statistical correction, the accuracy of is greatly improved. In the case of using statistical correction, the accuracy of is greatly improved with the lowest MAE value of 0.14 units (M062X; ). The calculated results of in this study have the same accuracy as the experimental measurements.
Tài liệu tham khảo
-
[1] Namazian and S. Halvani, "Calculations of pKa values of carboxylic acids in aqueous solution using density functional theory”, The Journal of Chemical Thermodynamics, vol. 38, pp. 1495-1502, 2006.
[2] Mansouri, N. F. Cariello, A. Korotcov, V. Tkachenko, C. M. Grulke, C. S. Sprankle, et al., "Open-source QSAR models for pKa prediction using multiple machine learning approaches”, Journal of cheminformatics, vol. 11, pp. 1-20, 2019.
[3] Jover, R. Bosque, and J. Sales, "QSPR prediction of pKa for benzoic acids in different solvents”, QSAR & Combinatorial Science, vol. 27, pp. 563-581, 2008.
[4] C. Shields and P. G. Seybold, Computational approaches for the prediction of pKa values: CRC Press, 2013.
[5] Hunt, L. Hosseini-Gerami, T. Chrien, J. Plante, D. J. Ponting, and M. Segall, "Predicting p K a Using a Combination of Semi-Empirical Quantum Mechanics and Radial Basis Function Methods”, Journal of chemical information and modeling, vol. 60, pp. 2989-2997, 2020.
[6] Casasnovas, J. Ortega‐Castro, J. Frau, J. Donoso, and F. Munoz, "Theoretical pKa calculations with continuum model solvents, alternative protocols to thermodynamic cycles”, International Journal of Quantum Chemistry, vol. 114, pp. 1350-1363, 2014.
[7] H. Jensen, C. J. Swain, and L. Olsen, "Prediction of p K a Values for Druglike Molecules Using Semiempirical Quantum Chemical Methods”, The Journal of Physical Chemistry A, vol. 121, pp. 699-707, 2017.
[8] Andrés-Lacueva, A. Medina-Remon, R. Llorach, M. Urpi-Sarda, N. Khan, G. Chiva-Blanch, et al., "Phenolic compounds: chemistry and occurrence in fruits and vegetables”, ed: Wiley Online Library, 2010, pp. 53-80.
[9] A. Vinson, Y. Hao, X. Su, and L. Zubik, "Phenol antioxidant quantity and quality in foods: vegetables”, Journal of agricultural and food chemistry, vol. 46, pp. 3630-3634, 1998.
[10] Chen, J. Yang, L. Ma, J. Li, N. Shahzad, and C. K. Kim, "Structure-antioxidant activity relationship of methoxy, phenolic hydroxyl, and carboxylic acid groups of phenolic acids”, Scientific reports, vol. 10, pp. 1-9, 2020.
[11] Aspée, C. Aliaga, L. Maretti, D. Zúñiga-Núñez, J. Godoy, E. Pino, et al., "Reaction kinetics of phenolic antioxidants toward photoinduced pyranine free radicals in biological models”, The Journal of Physical Chemistry B, vol. 121, pp. 6331-6340, 2017.
[12] A. Alberty, "Recommendations for nomenclature and tables in biochemical thermodynamics (IUPAC recommendations 1994)”, Pure and applied chemistry, vol. 66, pp. 1641-1666, 1994.
[13] Zhao, Z. Jin, and J. Wu, "New theoretical method for rapid prediction of solvation free energy in water”, The Journal of Physical Chemistry B, vol. 115, pp. 6971-6975, 2011.
[14] D. Becke, "A new mixing of Hartree–Fock and local density‐functional theories”, The Journal of chemical physics, vol. 98,
pp. 1372-1377, 1993.
[15] P. Perdew, M. Ernzerhof, and K. Burke, "Rationale for mixing exact exchange with density functional approximations”,
The Journal of chemical physics, vol. 105, pp. 9982-9985, 1996.
[16] -D. Chai and M. Head-Gordon, "Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections”, Physical Chemistry Chemical Physics, vol. 10, pp. 6615-6620, 2008.
[17] Zhao and D. G. Truhlar, "The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals”, Theoretical chemistry accounts, vol. 120, pp. 215-241, 2008.
[18] S. Bryantsev, "Predicting the stability of aprotic solvents in Li-air batteries: pKa calculations of aliphatic C–H acids in dimethyl sulfoxide”, Chemical Physics Letters, vol. 558, pp. 42-47, 2013.
[19] Huang, J. Jiang, M. Wen, and Z.-X. Wang, "Assessing the performance of commonly used DFT functionals in studying the chemistry of frustrated Lewis pairs”, Journal of Theoretical and Computational Chemistry, vol. 13, p. 1350074, 2014.
[20] Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, "Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions”, The Journal of chemical physics, vol. 72, pp. 650-654, 1980.
[21] Kheirjou, A. Abedin, A. Fattahi, and M. M. Hashemi, "Excellent response of the DFT study to the calculations of accurate relative pKa value of different benzo-substituted quinuclidines”, Computational and Theoretical Chemistry, vol. 1027, pp. 191-196, 2014.
[22] M. Carvalho, Y. A. d. O. Só, A. S. K. Wernik, M. d. A. Silva, and R. Gargano, "Accurate acid dissociation constant (pKa) calculation for the sulfachloropyridazine and similar molecules”, Journal of Molecular Modeling, vol. 27, pp. 1-9, 2021.
[23] Miertuš, E. Scrocco, and J. Tomasi, "Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects”, Chemical Physics, vol. 55, pp. 117-129, 1981.
[24] Alibakhshi and B. Hartke, "Improved prediction of solvation free energies by machine-learning polarizable continuum solvation model”, Nature communications, vol. 12, pp. 1-7, 2021.
[25] Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, et al., "Gaussian 16 revision a. 03. 2016; gaussian inc”, Wallingford CT, vol. 2, 2016.
[26] G. Tehan, E. J. Lloyd, M. G. Wong, W. R. Pitt, J. G. Montana, D. T. Manallack, et al., "Estimation of pka using semiempirical molecular orbital methods. part 1: Application to phenols and carboxylic acids”, Quantitative Structure‐Activity Relationships, vol. 21, pp. 457-472, 2002.
[27] D. Liptak, K. C. Gross, P. G. Seybold, S. Feldgus, and G. C. Shields, "Absolute p K a determinations for substituted phenols”, Journal of the American Chemical Society, vol. 124, pp. 6421-6427, 2002.
[28] C. Book, "Chemical Book”, [Online]Available: http://www. chemicalbook. com/ProductChemicalPropertiesCB8852597_ EN. htm, 2017.
##plugins.themes.academic_pro.article.sidebar##
