Abstract
Enthalpies of mixing of R- and S-enantiomers of dicarboxylic acids such as 2-methylbutanedioic acid (MBA), 2-hydroxylbutanedioic acid (HBA), 2-methylpentanedioic acid (MPA) and 2-hydroxyl-2-methylbutanedioic acid (HMBA) in ethanol solution have been measured for a large range of mole fraction of heterochiral dicarboxylic acid at 298.15 K. Also densities of ethanol solution of the dicarboxylic acids were determined. Enthalpies of mixing were exothermic for all the concentrations. Enthalpic stabilization on mixing was increased with decreasing concentration of all dicarboxylic acids measured. Sequence of enthalpic stabilization on mixing was MBA mixing was MBA<DHBA<MPA<HMBA<HBS at 0.5 mass%.
Similar content being viewed by others
References
S Takagi R Fujishiro K Amaya (1968) J. Chem. Soc. Chem. Commun. 1968 480
JP Guette D Boucherot A Horeau (1973) Tetrahedron Lett. 1973 465 Occurrence Handle10.1016/S0040-4039(01)95837-X
Z Atik MB Ewing ML McGlashan (1981) J. Phys. Chem. 85 3300 Occurrence Handle1:CAS:528:DyaL3MXlslKlu7o%3D Occurrence Handle10.1021/j150622a018
Z Atik MB Ewing ML McGlashan (1983) J. Chem. Thermodyn. 15 159 Occurrence Handle1:CAS:528:DyaL3sXhvVKltb0%3D Occurrence Handle10.1016/0021-9614(83)90155-6
L Leplori B Koppenhoefer (1994) J. Phys. Chem. 98 6862 Occurrence Handle10.1021/j100078a031
T Kimura T Ozaki S Takagi (1998) Chirality 10 275 Occurrence Handle10.1002/(SICI)1520-636X(1998)10:7<722::AID-CHIR20>3.0.CO;2-0
T Kimura T Ozaki S Takagi (2001) Enantiomers 6 5 Occurrence Handle1:CAS:528:DC%2BD3MXkslWms78%3D
T Kimura T Matsushita K Ueda T Matsuda F Aktar T Kamiyama M Fujisawa. (2004) Thermochim. Acta 414 209 Occurrence Handle1:CAS:528:DC%2BD2cXjsVCrtrw%3D Occurrence Handle10.1016/j.tca.2003.12.024
T Kimura MohdA Khan M Ishii K Ueda T Matsushita T Kamiyama M Fujisawa (2006) J. Chem. Thermodyn. 38 1042 Occurrence Handle1:CAS:528:DC%2BD28XmvFKlu7o%3D Occurrence Handle10.1016/j.jct.2005.10.019
T Kimura MohdA Khan T Kamiyama M Fujisawa (2006) J. Chem. Eng. Data. 51 909 Occurrence Handle1:CAS:528:DC%2BD28Xjtlaqtrk%3D Occurrence Handle10.1021/je050388j
T Kimura MohdA Khan M Ishii T Kamiyama M Fujisawa (2006) Chirality 18 581 Occurrence Handle1:CAS:528:DC%2BD28XnsFOjs7s%3D Occurrence Handle10.1002/chir.20285
T Kimura T Ozaki S Takeda Y Nakai S Takagi (1998) J. Thermal Anal. 54 275
T Kimura T Matsushita K Ueda T Tamura S Takagi (2001) J. Therm. Anal. Cal. 64 231 Occurrence Handle1:CAS:528:DC%2BD3MXktFyjsbo%3D Occurrence Handle10.1023/A:1011553500435
T Kimura T Matsushita K Ueda T Kamiyama S Takagi (2004) J. Chem. and Eng. Data 49 1046 Occurrence Handle1:CAS:528:DC%2BD2cXksFeks74%3D Occurrence Handle10.1021/je0499317
T Kimura Y Usui S Nishimura S Takagi (1989) J. Fac. Sci. Technol. Kinki Univ. 25 109
HyperChem version 7.01, HYPERCUBE, Inc.
Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.
Molecular Moldeling Pro, NorGwyn Montgomery Software Inc.
Private communication with Prof. H. Yokoyama. To be submitted.
T. Kimura and M. Fujisawa, Submitted.
G Castronuovo V Elia F Velleca (1996) J. Chem. Soc., Faraday Trans. 92 3093 Occurrence Handle1:CAS:528:DyaK28XlsVGhurs%3D Occurrence Handle10.1039/ft9969203093
G Castronuovo V Elia M Niccoli F Velleca (2001) Phys. Chem. Chem. Phys. 3 2488 Occurrence Handle1:CAS:528:DC%2BD3MXjvFyit7w%3D Occurrence Handle10.1039/b100987g
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kimura, T., Khan, M.A. & Kamiyama, T. Enthalpies of mixing and apparent molar volumes of ethanol solution of chiral dicarboxylic acids. J Therm Anal Calorim 85, 559–565 (2006). https://doi.org/10.1007/s10973-006-7662-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-006-7662-7