First-principles prediction of acidities in the gas and solution phase

Wiley Interdisciplinary Reviews: Computational Molecular Science

Volumn 1, Issue 5, 2011, Pages 649-660

  Ho, Junming ^a   Coote, Michelle L ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURATE PREDICTION; COMPUTATIONAL PROTOCOLS; CONTINUUM SOLVENTS; GAS AND SOLUTION PHASE; GAS-PHASE ACIDITIES; SOLVATION FREE ENERGIES; THERMODYNAMIC CYCLE; VARIOUS DENSITIES;

DENSITY FUNCTIONAL THEORY; FREE ENERGY; SOLVATION;

FORECASTING;

EID: 84858130853     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.43     Document Type: Article

References (58)

1. Curtiss LA, Raghavachari K, Redfern PC, Rassolov V, Pople JA. Gaussian-3 (G3) theory for molecules containing first and second-row atoms. J Chem Phys 1998, 109:7764-7777. doi:10.1063/1.477422.
2. Montgomery JA, Frisch MJ, Ochterski JW, Petersson GA. A complete basis set model chemistry. VI. Use of density functional theory geometries and frequencies. J Chem Phys 1999, 110:2822-2827.
3. Martin JM, Parthiban S. In: Cioslowski J, ed. W1 and W2 theories, and their variants: Thermochemistry in the kJ/mol accuracy range. Quantum Mechanical Prediction of Thermochemical Data. Dordrecht, the Netherlands: Kluwer-Academic; 2001, pp 31-65.
4. A. D. McNaught, A. Wilkinson. IUPAC. Compendium of Chemical Terminology. 2nd ed. Oxford: Blackwell Scientific Publications; 1997. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
5. Krol M, Wrona M, Page CS, Bates PA. Macroscopic pKa calculations of fluorescein and its derivatives. J Chem Theory Comput 2006, 2:1520-1529. doi: 10.1021/ct600235y.
6. McQuarrie DM. Statistical Mechanics. New York: Harper and Row; 1970.
7. McQuarrie D, Simon JD. Physical Chemistry: A Molecular Approach. Sausalito, California: University Science Books; 1997.
8. Atkins PW. Physical Chemistry. 6th ed. Oxford: Oxford University Press; 1998.
9. Fernandez-Ramos A, Ellingson BA, Meana-Paneda R, Marques JMC, Truhlar DG. Symmetry numbers and chemical reaction rates. Theor Chem Acc 2007, 118:813-826. doi: 10.1007/s00214-007-0328-0.
10. Lin CY, Izgorodina EI, Coote ML. How accurate are approximate methods for evaluating partition functions for hindered internal rotations? J Phys Chem A 2008, 112:1956-1964. doi: 10.1021/jp710341h.
11. Kirkpatrick S, Gelatt Jr. CD, Vecchi MP. Optimization by simulated annealing. Science 1983, 220:671-680. doi: 10.1126/science.220.4598.671.
12. Chang G, Guida WE, Still WC. An internal-coordinate Monte Carlo method for searching conformational space. J Am Chem Soc 1989, 111:4379-4386. doi: 10.1021/ja00194a035.
13. Izgorodina EI, Lin CY, Coote ML. Energy-directed tree search: an efficient systematic algorithm for finding the lowest energy conformation of molecules. Phys Chem Chem Phys 2007, 9:2507-2516. doi: 10.1039/B700938K.
14. Merrick JP, Moran D, Radom L. An evaluation of harmonic vibrational frequency scale factors. J Phys Chem A 2007, 111:11683-11700. doi: 10.1021/jp073974n.
15. Scott AP, Radom L. Harmonic vibrational frequencies: an evaluation of hartree-fock, moller-plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem 1996, 100:16502-16513. doi: 10.1021/jp960976r.
16. Ho J, Coote ML. pKa calculation of some biologically important carbon acids: an assessment of contemporary theoretical procedures. J Chem Theor Comput 2009, 5:295-306. doi: 10.1021/ct800335v.
17. Curtiss LA, Redfern PC, Raghavachari K, Rassolov V, Pople JA. Gaussian-3 theory using reduced Møller-Plesset order. J Chem Phys 1999, 110:4703-4709. doi:10.1063/1.478385.
18. Ho J, Coote ML. A universal approach to continuum solvent pKa calculations-are we there yet? Theor Chem Acc 2010, 125:3-21. doi: 10.1007/s00214-009-0667-0.
19. Vreven T, Morokuma K. On the application of the IMOMO (integrated molecular orbital + molecular orbital) method. J Comp Chem 2000, 21:1419-1432. doi: 10.1002/1096-987X(200012)21.
20. Vreven T, Morokuma K. The accurate calculation and prediction of the bond dissociation energies in a series of hydrocarbons using the IMOMO (integrated molecular orbital+molecular orbital) methods. J Chem Phys 1999, 111:8799-8803. doi:10.1063/1.480227.
21. Blinco JP, Hodgson JL, Morrow BJ, Walker JR, Will GD, Coote ML, Bottle SE. Experimental and theoretical studies of the redox potentials of cyclic nitroxides. J Org Chem 2008, 73:6763-6771. doi: 10.1021/jo801099w.
22. Hodgson JL, Namazian M, Bottle SE, Coote ML. One-electron oxidation and reduction potentials of nitroxide antioxidants: a theoretical study. J Phys Chem A 2007, 111:13595-13605. doi: 10.1021/jp074250e.
23. Lin CY, Izgorodina EI, Coote ML. First principles prediction of the propagation rate coefficients of acrylic and vinyl esters: are we there yet? Macromolecules 2010, 43:553-560. doi: 10.1021/ma902049g.
24. Brittain DRB, Lin CY, Gilbert ATB, Izgorodina EI, Gill PMW, Coote ML. DFT errors of some organic reactions. Phys Chem Chem Phys 2009, 11:1138-1142. doi: 10.1039/B818412G.
25. Zhang S, Baker J, Pulay P. A reliable and efficient first principles-based method for predicting pKa values. 1. Methodology. J Phys Chem A 2010, 114:425-431. doi: 10.1021/jp9067069.
26. Zhang S, Baker J, Pulay P. A reliable and efficient first principles-based method for predicting pKa values. 2. Organic acids. J Phys Chem A 2010, 114:432-442. doi: 10.1021/jp9067087.
27. Adam K. New density functional and atoms in molecules method of computing relative pKa values in solution. J Phys Chem A 2002, 106:11963-11972. doi: 10.1021/jp026577f.
28. Barone V, Cossi M, Tomasi J. A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J Chem Phys 1997, 107:3210-3221. doi:10.1063/1.474671.
29. Levy RM, Kitchen DB, Blair JT, Krogh-Jespersen K. Molecular dynamics simulation of time-resolved fluorescence and nonequilibrium solvation of formaldehyde in water. J Phys Chem 1990, 94:4470-4476.
30. Tomasi J, Mennucci B, Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005, 105:2999-3093. doi: 10.1021/cr9904009.
31. Cances MT, Mennucci B, Tomasi J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 1997, 107:3032-3041. doi:10.1063/1.474659.
32. Klamt A, Schurmann G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc, Perkin Trans 2 1993, 5:799-805. doi: 10.1039/P29930000799.
33. Cossi M, Rega N, Scalmani G, Barone V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem 2003, 24:669-681. doi: 10.1002/jcc.10189.
34. Barone V, Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A 1998, 102:1995-2001. doi: 10.1021/jp9716997.
35. Kelly CP, Cramer CJ, Truhlar DG. SM6: a density functional theory continuum solvation model for calculating aqueous solvation free energies of neutrals, ions, and solute-water clusters. J Chem Theor Comput 2005, 1:1133-1152. doi: 10.1021/ct050164b.
36. Marenich AV, Cramer CJ, Truhlar DG. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 2009, 113:6378-6396.
37. Klamt A. COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Amsterdam, the Netherlands: Elsevier Science Ltd.; 2005.
38. Klamt A, Jonas V, Burger T, Lohrenz JCW. Refinement and parametrization of COSMO-RS. J Phys Chem A 1998, 102:5074-5085. doi: 10.1021/jp980017s.
39. Klamt A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena. J Phys Chem 1995, 99:2224-2235. doi: 10.1021/j100007a062.
40. Tissandier MD, Cowen KA, Feng WY, Gundlach E, Cohen MH, Earhart AD, Coe JV. The proton's absolute aqueous enthalpy and gibbs free energy of solvation from cluster-ion solvation data. J Phys Chem A 1998, 102:7787-7794. doi: 10.1021/jp982638r.
41. Kelly CP, Cramer CJ, Truhlar DG. Aqueous solvation free Energies of ions and ion-water clusters based on an accurate value for the absolute aqueous solvation free energy of the proton. J Phys Chem B 2006, 110:16066-16081. doi: 10.1021/jp063552y.
42. Liptak MD, Shields GC. Accurate pKa calculations for carboxylic acids using complete basis set and Gaussian-n models combined with CPCM continuum solvation methods. J Am Chem Soc 2001, 123:7314-7319. doi: 10.1021/ja010534f.
43. Namazian M, Zakery M, Noorbala MR, Coote ML. Accurate calculation of the pKa of trifluoroacetic acid using high-level ab initio calculations. Chem Phys Lett 2008, 451:163-168. doi:10.1016/j.cplett.2007.11.088.
44. Liptak MD, Gross KC, Seybold PG, Feldgus S, Shields GC. Absolute pKa determinations for substituted phenols. J Am Chem Soc 2002, 124:6421-6427. doi: 10.1021/ja012474j.
45. Kallies B, Mitzner R. pKa values of amines in water from quantum mechanical calculations using a polarized dielectric continuum representation of the solvent. J Phys Chem B 1997, 101:2959-2967. doi: 10.1021/jp962708z.
46. Pliego JR Jr, Riveros JM. Theoretical calculation of pKa using the cluster-continuum model. J Phys Chem A 2002, 106:7434-7439. doi: 10.1021/jp025928n.
47. Kelly CP, Cramer CJ, Truhlar DG. Adding explicit solvent molecules to continuum solvent calculations for the calculation of aqueous acid dissociation constants. J Phys Chem A 2006, 110:2493-2499. doi: 10.1021/jp055336f.
48. Ding F, Smith JM, Wang H. First principles calculation of pKa values for organic acids in nonaqueous solution. J Org Chem 2009, 74:2679-2691. doi: 10.1021/jo802641r.
49. Fu Y, Liu L, Li R-Q, Liu R, Guo Q-X. First-principle predictions of absolute pKa's of organic acids in dimethyl sulfoxide solution. J Am Chem Soc 2004, 126:814-822. doi: 10.1021/ja0378097.
50. Eckert F, Diedenhofen M, Klamt A. Towards first principles prediction of pKa: COSMO-RS and the cluster-continuum approach. Mol Phys 2010, 108:229-241. doi: 10.1080/00268970903313667.
51. Pliego JR Jr, Riveros JM. The cluster-continuum model for the calculation of the solvation free energy of ionic species. J Phys Chem A 2001, 105:7241-7247. doi: 10.1021/jp004192w.
52. Takano Y, Houk KN. Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules. J Chem Theor Comput 2005, 1:70-77. doi: 10.1021/ct049977a.
53. Mobley DL, Dill KA, Chodera JD. Treating entropy and conformational changes in implicit solvent simulations of small molecules. J Phys Chem B 2008, 112:938-946. doi: 10.1021/jp0764384.
54. Klamt A, Eckert F, Diedenhofen M. Prediction of the free energy of hydration of a challenging set of pesticide-like compounds. J Phys Chem B 2009, 113:4508-4510. doi: 10.1021/jp805853y.
55. Cramer CJ. Essentials of Computational Chemistry: Theories and Models. 2nd ed. Chichester, England: John Wiley & Sons; 2004.
56. Gordon MS, Mullin JM, Pruitt SR, Roskop LB, Slipchenko LV, Boatz JA. Accurate methods for large molecular systems. J Phys Chem B 2009, 113:9646-9663.
57. Guthrie JP. A blind challenge for computational solvation free energies: introduction and overview. J Phys Chem B 2009, 113:4501-4507.
58. Mennucci B. Continuum solvation models: what else can we learn from them? J Phys Chem Lett 2010, 1:1666-1674.