Prediction of the aqueous solvation free energy of organic compounds by using autocorrelation of molecular electrostatic potential surface properties combined with response surface analysis

Michielan, Lisa; Bacilieri, Magdalena; Kaseda, Chosei; Moro, Stefano

doi:10.1016/j.bmc.2008.03.064

Cited by 32 publications

(28 citation statements)

References 22 publications

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“…[30][31][32] Direct comparison of calculated and experimental values of solvation energies is available only for nitrobenzene, for which literature data provides a solvation free energy of neutral molecule (-4.17 kcal/mol or 20.177 V). 33 This value is in good agreement with the data provided by the most SMD models.…”

Section: Gibbs Solvation Free Energysupporting

confidence: 86%

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Sviatenko

Isayev

Gorb³

et al. 2011

J Comput Chem

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A number of density functionals was utilized for the calculation of electron attachment free energy for nitrocompounds, quinones and azacyclic compounds. Different solvation models have been tested on the calculation of difference in free energies of solvation of oxidized and reduced forms of nitrocompounds in aqueous solution, quinones in acetonitrile, and azacyclic compounds in dimethylformamide. Gas-phase free energies evaluated at the mPWB1K/tzvp level and solvation energies obtained using SMD model to compute solvation energies of neutral oxidized forms and PCM(Pauling) to compute solvation energies of anion-radical reduced forms provide reasonable accuracy of the prediction of electron attachment free energy, difference in free solvation energies of oxidized and reduced forms, and as consequence yield reduction potentials in good agreement with experimental data (mean absolute deviation is 0.15 V). It was also found that SMD/M05-2X/tzvp method provides reduction potentials with deviation of 0.12 V from the experimental values but in cases of nitrocompounds and quinones this accuracy is achieved due to the cancelation of errors. To predict reduction ability of naturally occurred iron containing species with respect to organic pollutants we exploited experimental data within the framework of Pourbaix (Eh - pH) diagrams. We conclude that surface-bound Fe(II) as well as certain forms of aqueous Fe(II)aq are capable of reducing a variety of nitroaromatic compounds, quinones and novel high energy materials under basic conditions (pH > 8). At the same time, zero-valent iron is expected to be active under neutral and acidic conditions.

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Section: Gibbs Solvation Free Energysupporting

confidence: 86%

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Sviatenko

Isayev

Gorb³

et al. 2011

J Comput Chem

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“…[47][48][49] Chamberlin et al givea no verview of the experimental methods available to derive DG hyd . [50] Six quantum mechanical methods were investigated using the main stream 6-31 + G(d, p)//6-311 + G(2df,p)b asis set combination.…”

Section: Benchmarkingmentioning

confidence: 99%

“…These consisto ft he 100 organic molecules used in the benchmarking set in addition to 40 compounds with known hydration energy values. [47,69] These are indeed small simple organic compounds such as methane, cyclohexene and anisole. The average MW of this collection is 117.6 g/molw ith log Pa t2 .1, with low values for the rest of the molecular descriptors investigated.…”

Section: The Octanolàwater Partition Coefficient (Log P)mentioning

confidence: 99%

Hydration Free Energy as a Molecular Descriptor in Drug Design: A Feasibility Study

Zafar

Reynisson

2016

Molecular Informatics

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In this work the idea was investigated whether calculated hydration energy (ΔGhyd ) can be used as a molecular descriptor in defining promising regions of chemical space for drug design. Calculating ΔGhyd using the Density Solvation Model (SMD) in conjunction with the density functional theory (DFT) gave an excellent correlation with experimental values. Furthermore, calculated ΔGhyd correlates reasonably well with experimental water solubility (r(2) =0.545) and also log P (r(2) =0.530). Three compound collections were used: Known drugs (n=150), drug-like compounds (n=100) and simple organic compounds (n=140). As an approximation only molecules, which do not de/protonate at physiological pH were considered. A relatively broad distribution was seen for the known drugs with an average at -15.3 kcal/mol and a standard deviation of 7.5 kcal/mol. Interestingly, much lower averages were found for the drug-like compounds (-7.5 kcal/mol) and the simple organic compounds (-3.1 kcal/mol) with tighter distributions; 4.3 and 3.2 kcal/mol, respectively. This trend was not observed for these collections when calculated log P and log S values were used. The considerable greater exothermic ΔGhyd average for the known drugs clearly indicates in order to develop a successful drug candidate value of ΔGhyd <-5 kcal/mol or less is preferable.

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“…53,54,87,95,96,115 The problems associated with Group Contribution approaches have meant that recently the majority of QSPR publications on the prediction of solvation free energy have tended to use other sets of molecular descriptors. 54,95,96,[112][113][114][115]121 Despite the more advanced nature of these QSPR models as compared to GC approaches, the majority of them still not extrapolate well to molecules dissimilar to those in the training dataset. The full theoretical background of these methods has been the subject of a large number of excellent review articles and books (see also above) and will not be recapitulated here.…”

Section: Available Experimental Sfe Datamentioning

confidence: 99%

Solvation Thermodynamics of Organic Molecules by the Molecular Integral Equation Theory: Approaching Chemical Accuracy

2015

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Prediction of the aqueous solvation free energy of organic compounds by using autocorrelation of molecular electrostatic potential surface properties combined with response surface analysis

Cited by 32 publications

References 22 publications

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Toward robust computational electrochemical predicting the environmental fate of organic pollutants

Hydration Free Energy as a Molecular Descriptor in Drug Design: A Feasibility Study

Solvation Thermodynamics of Organic Molecules by the Molecular Integral Equation Theory: Approaching Chemical Accuracy

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