Enthalpies of vaporization of aliphatic C5 and C6 alcohols

Majer, Vladimı́r; Svoboda, V.; Uchytilová, V.; Finke, M.

doi:10.1016/0378-3812(85)90026-3

Cited by 44 publications

(49 citation statements)

References 16 publications

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“…86) are much smaller than the other resources. For acetic acid, the CRC value of 23.36 kJ/mol is less than half of the values reported by Majer and Svoboda (51.6 kJ/mol), 23 and Konicek and Wadso (51.6 ± 1.5 kJ/mol); 31 for propanoic acid, the CRC value of 32.14 kJ/mol is also much smaller than the values reported by Majer and Svoboda (55.0 kJ/mol), 23 and Konicek and Wadso (55.0 ± 2.0 kJ/mol). 31 We adopted the values of Majer and Svoboda in this work, not only because they are relatively newer, but also the calculated heats of vaporization by both GAFF and OPLS reproduce their experimental values well.…”

Section: Methodscontrasting

confidence: 56%

“…86) unless explicitly noted. Other experimental data resources include the publications of Majer and Svoboda, 23 Kemp and Egan 24 , Pedley et al, 25 Wiberg et al, 26 Geller, 27 Pihlaja and Heikklia, 28 and Steele et al 29 When multiple experimental data are available for a compound, the overall guidance is to use the latest one. However, for 9 compounds (Nos.…”

Section: Methodsmentioning

confidence: 99%

“… a # res – the number of residues (# res) in a simulation box; # atom – the number of atoms in a residue b densities were measured with pressure larger than 1atm (propene, 1,3-butadiene, methylamine, trimethylamine). c Ref. 23;…”

Section: Figurementioning

confidence: 99%

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Application of Molecular Dynamics Simulations in Molecular Property Prediction. 1. Density and Heat of Vaporization

Wang

Hou

2011

J. Chem. Theory Comput.

124

148

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Molecular mechanical force field (FF) methods are useful in studying condensed phase properties. They are complementary to experiment and can often go beyond experiment in atomic details. Even a FF is specific for studying structures, dynamics and functions of biomolecules, it is still important for the FF to accurately reproduce the experimental liquid properties of small molecules that represent the chemical moieties of biomolecules. Otherwise, the force field may not describe the structures and energies of macromolecules in aqueous solutions properly. In this work, we have carried out a systematic study to evaluate the General AMBER Force Field (GAFF) in studying densities and heats of vaporization for a large set of organic molecules that covers the most common chemical functional groups. The latest techniques, such as the particle mesh Ewald (PME) for calculating electrostatic energies, and Langevin dynamics for scaling temperatures, have been applied in the molecular dynamics (MD) simulations. For density, the average percent error (APE) of 71 organic compounds is 4.43% when compared to the experimental values. More encouragingly, the APE drops to 3.43% after the exclusion of two outliers and four other compounds for which the experimental densities have been measured with pressures higher than 1.0 atm. For heat of vaporization, several protocols have been investigated and the best one, P4/ntt0, achieves an average unsigned error (AUE) and a root-mean-square error (RMSE) of 0.93 and 1.20 kcal/mol, respectively. How to reduce the prediction errors through proper van der Waals (vdW) parameterization has been discussed. An encouraging finding in vdW parameterization is that both densities and heats of vaporization approach their “ideal” values in a synchronous fashion when vdW parameters are tuned. The following hydration free energy calculation using thermodynamic integration further justifies the vdW refinement. We conclude that simple vdW parameterization can significantly reduce the prediction errors. We believe that GAFF can greatly improve its performance in predicting liquid properties of organic molecules after a systematic vdW parameterization, which will be reported in a separate paper.

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Section: Methodscontrasting

confidence: 56%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Application of Molecular Dynamics Simulations in Molecular Property Prediction. 1. Density and Heat of Vaporization

Wang

Hou

2011

J. Chem. Theory Comput.

124

148

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“… a Ref 151. b Ref 152. c Ref 153. d Ref 154. e Ref 155. f Ref 156. g Ref 157. h Ref 158. i Ref 159. j Ref 160. k Ref 161. l Ref 162. m Ref 163. n Ref 164. o Ref 165. p Ref 166. q Ref 167. r Ref 168. s Ref 169. t Ref 170. u Ref 171. v Ref 172. w Ref 173. x Ref 174. y Ref 175. z Ref 176. aa Ref 177. bb Ref 178. cc Ref 179. …”

Section: Figurementioning

confidence: 99%

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

Ren

Ponder

2011

J. Chem. Theory Comput.

432

690

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An empirical potential based on permanent atomic multipoles and atomic induced dipoles is reported for alkanes, alcohols, amines, sulfides, aldehydes, carboxylic acids, amides, aromatics and other small organic molecules. Permanent atomic multipole moments through quadrupole moments have been derived from gas phase ab initio molecular orbital calculations. The van der Waals parameters are obtained by fitting to gas phase homodimer QM energies and structures, as well as experimental densities and heats of vaporization of neat liquids. As a validation, the hydrogen bonding energies and structures of gas phase heterodimers with water are evaluated using the resulting potential. For 32 homo- and heterodimers, the association energy agrees with ab initio results to within 0.4 kcal/mol. The RMS deviation of hydrogen bond distance from QM optimized geometry is less than 0.06 Å. In addition, liquid self-diffusion and static dielectric constants computed from molecular dynamics simulation are consistent with experimental values. The force field is also used to compute the solvation free energy of 27 compounds not included in the parameterization process, with a RMS error of 0.69 kcal/mol. The results obtained in this study suggest the AMOEBA force field performs well across different environments and phases. The key algorithms involved in the electrostatic model and a protocol for developing parameters are detailed to facilitate extension to additional molecular systems.

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“…Enthalpies of vaporization of solutes were taken from literature [35] and molar volumes were calculated from densities taken from literature [36]. The values of B 11 were calculated using the McGlashan and Potter [37] equation for alkanes and Tsonopolous [38] equation for the rest of solvents.…”

Section: Calculation Of Solubility Parametersmentioning

confidence: 99%

The Solubility Parameters of Ionic Liquids

Marciniak

2010

IJMS

111

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The Hildebrand’s solubility parameters have been calculated for 18 ionic liquids from the inverse gas chromatography measurements of the activity coefficients at infinite dilution. Retention data were used for the calculation. The solubility parameters are helpful for the prediction of the solubility in the binary solvent mixtures. From the solubility parameters, the standard enthalpies of vaporization of ionic liquids were estimated.

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Enthalpies of vaporization of aliphatic C5 and C6 alcohols

Cited by 44 publications

References 16 publications

Application of Molecular Dynamics Simulations in Molecular Property Prediction. 1. Density and Heat of Vaporization

Application of Molecular Dynamics Simulations in Molecular Property Prediction. 1. Density and Heat of Vaporization

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

The Solubility Parameters of Ionic Liquids

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