Resumen
From a density functional theory (DFT) analysis of solvation and the different components which comprise the free energy of solvation we propose quantitative structure-property relationship (QSPR) models to predict free energy of solvation, Δ GS 0, of organic compounds in seven alkane solvents (n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, and n-hexadecane). The data contains 151 structurally different compounds containing diverse organic functions: unbranched and branched alkanes, cycloalkanes, aromatics, alcohols, aldehydes, ketones, esters, ethers, amines, nitriles, pyridines, fluorinated hydrocarbons, thiols, sulfides, carboxylic acids and nitro hydrocarbons; covering a Δ GS 0 range from about -50 to 0 kJ/mol. The models for the seven n-alkane solvents contain the same two molecular descriptors, one DFT descriptor (softness) and one geometric (molecular surface area). This fact suggests that the physical mechanisms behind the solvation of organic compounds in n-alkane solvents are of the same nature, as expected from the similar physical and chemical properties of alkanes. The models proposed have the merit of predicting free energy of solvation in alkane solvents with fewer descriptors than other QSPR models reported in the literature having similar statistics, allowing in this way a well-defined physical interpretation. The two descriptors have definite physical meaning corresponding to the different components which comprise free energy of solvation. Thus, the models proposed reach the desired compromise among simpleness, physical interpretation and computation time.
| Idioma original | English |
|---|---|
| Páginas (desde-hasta) | 220-224 |
| Número de páginas | 5 |
| Publicación | Chemical Physics |
| Volumen | 325 |
| N.º | 2-3 |
| DOI | |
| Estado | Published - 20 jun 2006 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Spectroscopy
- Atomic and Molecular Physics, and Optics
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DFT derived solvation models for organic compounds in alkane solvents. / Delgado, Eduardo J.; Alderete, Joel B.; Jaña, Gonzalo A.
En: Chemical Physics, Vol. 325, N.º 2-3, 20.06.2006, p. 220-224.Resultado de la investigación: Article
TY - JOUR
T1 - DFT derived solvation models for organic compounds in alkane solvents
AU - Delgado, Eduardo J.
AU - Alderete, Joel B.
AU - Jaña, Gonzalo A.
PY - 2006/6/20
Y1 - 2006/6/20
N2 - From a density functional theory (DFT) analysis of solvation and the different components which comprise the free energy of solvation we propose quantitative structure-property relationship (QSPR) models to predict free energy of solvation, Δ GS 0, of organic compounds in seven alkane solvents (n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, and n-hexadecane). The data contains 151 structurally different compounds containing diverse organic functions: unbranched and branched alkanes, cycloalkanes, aromatics, alcohols, aldehydes, ketones, esters, ethers, amines, nitriles, pyridines, fluorinated hydrocarbons, thiols, sulfides, carboxylic acids and nitro hydrocarbons; covering a Δ GS 0 range from about -50 to 0 kJ/mol. The models for the seven n-alkane solvents contain the same two molecular descriptors, one DFT descriptor (softness) and one geometric (molecular surface area). This fact suggests that the physical mechanisms behind the solvation of organic compounds in n-alkane solvents are of the same nature, as expected from the similar physical and chemical properties of alkanes. The models proposed have the merit of predicting free energy of solvation in alkane solvents with fewer descriptors than other QSPR models reported in the literature having similar statistics, allowing in this way a well-defined physical interpretation. The two descriptors have definite physical meaning corresponding to the different components which comprise free energy of solvation. Thus, the models proposed reach the desired compromise among simpleness, physical interpretation and computation time.
AB - From a density functional theory (DFT) analysis of solvation and the different components which comprise the free energy of solvation we propose quantitative structure-property relationship (QSPR) models to predict free energy of solvation, Δ GS 0, of organic compounds in seven alkane solvents (n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, and n-hexadecane). The data contains 151 structurally different compounds containing diverse organic functions: unbranched and branched alkanes, cycloalkanes, aromatics, alcohols, aldehydes, ketones, esters, ethers, amines, nitriles, pyridines, fluorinated hydrocarbons, thiols, sulfides, carboxylic acids and nitro hydrocarbons; covering a Δ GS 0 range from about -50 to 0 kJ/mol. The models for the seven n-alkane solvents contain the same two molecular descriptors, one DFT descriptor (softness) and one geometric (molecular surface area). This fact suggests that the physical mechanisms behind the solvation of organic compounds in n-alkane solvents are of the same nature, as expected from the similar physical and chemical properties of alkanes. The models proposed have the merit of predicting free energy of solvation in alkane solvents with fewer descriptors than other QSPR models reported in the literature having similar statistics, allowing in this way a well-defined physical interpretation. The two descriptors have definite physical meaning corresponding to the different components which comprise free energy of solvation. Thus, the models proposed reach the desired compromise among simpleness, physical interpretation and computation time.
KW - Alkanes
KW - DFT
KW - Quantitative structure-property relationship
KW - Solvation
UR - http://www.scopus.com/inward/record.url?scp=33745085488&partnerID=8YFLogxK
U2 - 10.1016/j.chemphys.2005.12.011
DO - 10.1016/j.chemphys.2005.12.011
M3 - Article
AN - SCOPUS:33745085488
VL - 325
SP - 220
EP - 224
JO - Chemical Physics
JF - Chemical Physics
SN - 0301-0104
IS - 2-3
ER -