Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge

Jean-Claude Bradley; Michael H Abraham; William E Acree Jr; Andrew Sid Lang; Samantha N Beck; David A Bulger; Elizabeth A Clark; Lacey N Condron; Stephanie T Costa; Evan M Curtin; Sozit B Kurtu; Mark I Mangir; Matthew J McBride

doi:10.1186/s13065-015-0080-9

Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge

Chem Cent J. 2015 Mar 22:9:11. doi: 10.1186/s13065-015-0080-9. eCollection 2015.

Affiliations

¹ Department of Chemistry, Drexel University, Disque Hall Rm. 305. 3141 Chestnut Street, Philadelphia, PA 19104 USA.
² Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ UK.
³ Department of Chemistry, University of North Texas, 1155 Union Circle Drive #305070, Denton, TX 76203 USA.
⁴ Department of Computing and Mathematics, Oral Roberts University, Tulsa, OK 74171 USA.

Abstract

Background: Calculating Abraham descriptors from solubility values requires that the solute have the same form when dissolved in all solvents. However, carboxylic acids can form dimers when dissolved in non-polar solvents. For such compounds Abraham descriptors can be calculated for both the monomeric and dimeric forms by treating the polar and non-polar systems separately. We illustrate the method of how this can be done by calculating the Abraham descriptors for both the monomeric and dimeric forms of trans-cinnamic acid, the first time that descriptors for a carboxylic acid dimer have been obtained.

Results: Abraham descriptors were calculated for the monomeric form of trans-cinnamic acid using experimental solubility measurements in polar solvents from the Open Notebook Science Challenge together with a number of water-solvent partition coefficients from the literature. Similarly, experimental solubility measurements in non-polar solvents were used to determine Abraham descriptors for the trans-cinnamic acid dimer.

Conclusion: Abraham descriptors were calculated for both the monomeric and dimeric forms of trans-cinnamic acid. This allows for the prediction of further solubilities of trans-cinnamic acid in both polar and non-polar solvents with an error of about 0.10 log units. Graphical abstractMolar concentration of trans-cinnamic acid in various polar and non-polar solvents.