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

Chemistry Central Journal
Jean-Claude BradleyMatthew J McBride

Abstract

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. 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. 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 ...Continue Reading

References

Mar 26, 2003·Journal of Chemical Information and Computer Sciences·Christoph SteinbeckEgon Willighagen
May 25, 2004·Journal of Chemical Information and Computer Sciences·Jesús JoverJoaquim Sales
Jun 25, 2004·Journal of Chromatography. a·Michael H AbrahamAndreas M Zissimos
Oct 19, 2005·Journal of Computer-aided Molecular Design·Igor V TetkoVolodymyr V Prokopenko
Apr 22, 2006·The Journal of Organic Chemistry·Michael H AbrahamLee Griffiths
Feb 20, 2009·Journal of Chemical Information and Modeling·Junmei WangXiaojie Xu
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Oct 13, 2009·International Journal of Pharmaceutics·Parijat Jain, Samuel H Yalkowsky

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Citations

Dec 18, 2015·Analytical and Bioanalytical Chemistry·Andreas KremserTorsten C Schmidt
Mar 26, 2016·Journal of Pharmaceutical Sciences·Doaa Alantary, Samuel Yalkowsky
Oct 6, 2015·Chemistry Central Journal·Michael A Buonaiuto, Andrew S I D Lang
Mar 27, 2015·Applied Biochemistry and Biotechnology·Jung-Ho KimYung-Hun Yang
Sep 19, 2019·História, ciências, saúde--Manguinhos·Paulo Roberto Eliandos SantosFrancisco Dos Santos Lourenço
Mar 24, 2015·Chemistry Central Journal·Jean-Claude BradleyAndrew Sid Lang

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Software Mentioned

Absolv ACD / ADME Suite
Open Notebook Science
Open Source Chemistry Development Kit
ChemSpider
ALOGPS

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