Skip to content

Research at St Andrews

Are the sublimation thermodynamics of organic molecules predictable?

Research output: Contribution to journalArticlepeer-review

Author(s)

James L. McDonagh, David S. Palmer, Tanja van Mourik, John B. O. Mitchell

School/Research organisations

Abstract

We compare a range of computational methods for the prediction of sublimation thermodynamics (enthalpy, entropy and free energy of sublimation). These include a model from theoretical chemistry that utilizes crystal lattice energy minimization (with the DMACRYS program) and QSPR models generated by both machine learning (Random Forest and Support Vector Machines) and regression (Partial Least Squares) methods. Using these methods we investigate the predictability of the enthalpy, entropy and free energy of sublimation, with consideration of whether such a method may be able to improve solubility prediction schemes. Previous work has suggested that the major source of error in solubility prediction schemes involving a thermodynamic cycle via the solid state is in the modeling of the free energy change away from the solid state. Yet contrary to this conclusion other work has found that the inclusion of terms such as the enthalpy of sublimation in QSPR methods does not improve the predictions of solubility. We suggest the use of theoretical chemistry terms, detailed explicitly in the methods section, as descriptors for the prediction of the enthalpy and free energy of sublimation. A dataset of 158 molecules with experimental sublimation thermodynamics values and some CSD refcodes has been collected from the literature and is provided with their original source references.
Close

Details

Original languageEnglish
Pages (from-to)2162-2179
JournalJournal of Chemical Information and Modeling
Volume56
Issue number11
Early online date17 Oct 2016
DOIs
Publication statusPublished - 28 Nov 2016

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. A review of methods for the calculation of solution free energies and the modelling of systems in solution

    Skyner, R. E., McDonagh, J. L., Groom, C. R., van Mourik, T. & Mitchell, J. B. O., 17 Mar 2015, In: Physical Chemistry Chemical Physics. 17, 9, p. 6174-6191

    Research output: Contribution to journalArticlepeer-review

  2. Uniting cheminformatics and chemical theory to predict the intrinsic aqueous solubility of crystalline druglike molecules

    McDonagh, J., Nath, N., De Ferrari, L., van Mourik, T. & Mitchell, J. B. O., 24 Feb 2014, In: Journal of Chemical Information and Modeling. 54, 3, p. 844-856 13 p.

    Research output: Contribution to journalArticlepeer-review

  3. First-Principles Calculation of the Intrinsic Aqueous Solubility of Crystalline Druglike Molecules

    Palmer, D. S., McDonagh, J. L., Mitchell, J. B. O., van Mourik, T. & Fedorov, M. V., Sep 2012, In: Journal of Chemical Theory and Computation. 8, 9, p. 3322-3337 16 p.

    Research output: Contribution to journalArticlepeer-review

Related by journal

  1. Computational comparison of imidazoline association with the 12 binding site in human monoamine oxidases

    Basile, L., Pappalardo, M., Guccione, S., Milardi, D. & Ramsay, R. R., Apr 2014, In: Journal of Chemical Information and Modeling. 54, 4, p. 1200-1207 8 p.

    Research output: Contribution to journalArticlepeer-review

  2. Erratum: "in silico target predictions: Defining a benchmarking data set and comparison of performance of the multiclass naïve bayes and parzen-rosenblatt window"

    Koutsoukas, A., Lowe, R., Kalantarmotamedi, Y., Mussa, H. Y., Klaffke, W., Mitchell, J. B. O., Glen, R. C. & Bender, A., 28 Jul 2014, In: Journal of Chemical Information and Modeling. 54, 7, p. 2180-2182 3 p.

    Research output: Contribution to journalComment/debatepeer-review

  3. Erratum: Computational comparison of imidazoline association with the i2 binding site in human monoamine oxidases (Journal of Chemical Information and Modeling (2014) 54:4 (1200-1207))

    Basile, L., Pappalardo, M., Guccione, S., Milardi, D. & Ramsay, R. R., 28 Jul 2014, In: Journal of Chemical Information and Modeling. 54, 7, 1 p.

    Research output: Contribution to journalComment/debatepeer-review

  4. Uniting cheminformatics and chemical theory to predict the intrinsic aqueous solubility of crystalline druglike molecules

    McDonagh, J., Nath, N., De Ferrari, L., van Mourik, T. & Mitchell, J. B. O., 24 Feb 2014, In: Journal of Chemical Information and Modeling. 54, 3, p. 844-856 13 p.

    Research output: Contribution to journalArticlepeer-review

ID: 247062978

Top