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Adding Explicit Solvent Molecules to Continuum Solvent Calculations for the Calculation of Aqueous Acid Dissociation Constants

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Kelly, Casey P., Cramer, Christopher J., Truhlar, Donald G.·2006·The Journal of Physical Chemistry A

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Abstract

Aqueous acid dissociation free energies for a diverse set of 57 monoprotic acids have been calculated using a combination of experimental and calculated gas and liquid-phase free energies. For ionic species, aqueous solvation free energies were calculated using the recently developed SM6 continuum solvation model. This model combines a dielectric continuum with atomic surface tensions to account for bulk solvent effects. For some of the acids studied, a combined approach that involves attaching a single explicit water molecule to the conjugate base (anion), and then surrounding the resulting anion-water cluster by a dielectric continuum, significantly improves the agreement between the calculated pK(a) value and experiment. This suggests that for some anions, particularly those concentrating charge on a single exposed heteroatom, augmenting implicit solvent calculations with a single explicit water molecule is required, and adequate, to account for strong short-range hydrogen bonding interactions between the anion and the solvent. We also demonstrate the effect of adding several explicit waters by calculating the pK(a) of bicarbonate (HCO(3)(-)) using as the conjugate base carbonate (CO(3)(2-)) bound by up to three explicit water molecules.

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Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions
Krishnan, R., Binkley, J. S., Seeger, R., & Pople, J. A. (1980) · The Journal of Chemical Physics · doi:10.1063/1.438955 · Cited by 17,772
Quantum Mechanical Continuum Solvation Models
Tomasi, J., Mennucci, B., & Cammi, R. (2005) · Chemical Reviews · doi:10.1021/cr9904009 · Cited by 16,868
Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets
Frisch, M. J., Pople, J. A., & Binkley, J. S. (1984) · The Journal of Chemical Physics · doi:10.1063/1.447079 · Cited by 8,561
Nist chemistry webbook, nist standard reference database number 69
Linstorm, P. (1998) · Medical Entomology and Zoology · Cited by 4,606
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Klamt, A. (1995) · The Journal of Physical Chemistry · doi:10.1021/j100007a062 · Cited by 4,118
Ab initio study of solvated molecules: a new implementation of the polarizable continuum model
Cossi, M., Barone, V., Cammi, R., & Tomasi, J. (1996) · Chemical Physics Letters · doi:10.1016/0009-2614(96)00349-1 · Cited by 3,440
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Adamo, C., & Barone, V. (1998) · The Journal of Chemical Physics · doi:10.1063/1.475428 · Cited by 3,436
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Curtiss, L. A., Raghavachari, K., Redfern, P. C., Rassolov, V., & Pople, J. A. (1998) · The Journal of Chemical Physics · doi:10.1063/1.477422 · Cited by 2,865
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Miertus̃, S., & Tomasi, J. (1982) · Chemical Physics · doi:10.1016/0301-0104(82)85072-6 · Cited by 2,475
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Barone, V., Cossi, M., & Tomasi, J. (1997) · The Journal of Chemical Physics · doi:10.1063/1.474671 · Cited by 2,406
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Authors: Kelly, C. P., Cramer, C. J., & Truhlar, D. G.
Venue: The Journal of Physical Chemistry A
Publisher: American Chemical Society (ACS)
Published: 2006-02-01
Volume: 110
Issue: 7
Pages: 2493-2499
ISSN: 1089-5639 (ISSN-L)
1520-5215
DOI: 10.1021/jp055336f
OpenAlex: W2155273994
Cited by: 445
References: 55
FWCI: 15.46
Type: journal article
Language: en
Open access: green

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Adding Explicit Solvent Molecules to Continuum Solvent Calculations for the Calculation of Aqueous Acid Dissociation Constants

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