Aqueous solubility of organic salts. Investigating trends in a systematic series of 51 crystalline salt forms of methylephedrine

Lygia S. de Moraes, Darren Edwards, Alastair J. Florence, Andrea Johnston, Blair F. Johnston, Catriona A. Morrison, Alan R. Kennedy

Research output: Contribution to journalArticle

8 Citations (Scopus)
17 Downloads (Pure)

Abstract

A dataset consisting of structures and aqueous solubility and melting point data for 51 salt forms of the phenylethylamine base methylephedrine is presented. Analysis showed correlation between solubility and melting point and between melting point of the salt and melting point of the parent acid, but no correlation of salt solubility with solubility of the parent acid. Identification of associations was aided by examining chemically sensible subgroups of the dataset, and this approach highlighted significantly different relationships between solubility and melting point for these subgroups. Thus, for example, the expected negative correlation between solubility and melting point was found for 24 anhydrous benzoate salts, but a positive correlation observed for 8 halide salts. Hydrated forms were anomalous. Packing analysis identified groups of structures that were isostructural with respect to cation packing. Correlation between solubility and melting point was found to be greatest within these isostructural groups, implying a role for packing structure in determining solubility.
Original languageEnglish
Pages (from-to)3277-3286
Number of pages10
JournalCrystal Growth and Design
Volume17
Issue number6
Early online date25 Apr 2017
DOIs
Publication statusPublished - 7 Jun 2017

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melting points
solubility
Solubility
Melting point
Salts
Crystalline materials
salts
trends
subgroups
Phenethylamines
acids
Acids
N-methylephedrine
Benzoates
halides
Cations
Positive ions
cations

Keywords

  • aqueous solubility
  • organic salts
  • methylephedrine
  • anhydrous benzoate salts
  • halide salts
  • active pharmaceutical ingredients
  • physicochemical data
  • crystal diffraction

Cite this

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title = "Aqueous solubility of organic salts. Investigating trends in a systematic series of 51 crystalline salt forms of methylephedrine",
abstract = "A dataset consisting of structures and aqueous solubility and melting point data for 51 salt forms of the phenylethylamine base methylephedrine is presented. Analysis showed correlation between solubility and melting point and between melting point of the salt and melting point of the parent acid, but no correlation of salt solubility with solubility of the parent acid. Identification of associations was aided by examining chemically sensible subgroups of the dataset, and this approach highlighted significantly different relationships between solubility and melting point for these subgroups. Thus, for example, the expected negative correlation between solubility and melting point was found for 24 anhydrous benzoate salts, but a positive correlation observed for 8 halide salts. Hydrated forms were anomalous. Packing analysis identified groups of structures that were isostructural with respect to cation packing. Correlation between solubility and melting point was found to be greatest within these isostructural groups, implying a role for packing structure in determining solubility.",
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Aqueous solubility of organic salts. Investigating trends in a systematic series of 51 crystalline salt forms of methylephedrine. / S. de Moraes, Lygia; Edwards, Darren; Florence, Alastair J.; Johnston, Andrea; Johnston, Blair F.; Morrison, Catriona A.; Kennedy, Alan R.

In: Crystal Growth and Design, Vol. 17, No. 6, 07.06.2017, p. 3277-3286.

Research output: Contribution to journalArticle

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T1 - Aqueous solubility of organic salts. Investigating trends in a systematic series of 51 crystalline salt forms of methylephedrine

AU - S. de Moraes, Lygia

AU - Edwards, Darren

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AU - Johnston, Andrea

AU - Johnston, Blair F.

AU - Morrison, Catriona A.

AU - Kennedy, Alan R.

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N2 - A dataset consisting of structures and aqueous solubility and melting point data for 51 salt forms of the phenylethylamine base methylephedrine is presented. Analysis showed correlation between solubility and melting point and between melting point of the salt and melting point of the parent acid, but no correlation of salt solubility with solubility of the parent acid. Identification of associations was aided by examining chemically sensible subgroups of the dataset, and this approach highlighted significantly different relationships between solubility and melting point for these subgroups. Thus, for example, the expected negative correlation between solubility and melting point was found for 24 anhydrous benzoate salts, but a positive correlation observed for 8 halide salts. Hydrated forms were anomalous. Packing analysis identified groups of structures that were isostructural with respect to cation packing. Correlation between solubility and melting point was found to be greatest within these isostructural groups, implying a role for packing structure in determining solubility.

AB - A dataset consisting of structures and aqueous solubility and melting point data for 51 salt forms of the phenylethylamine base methylephedrine is presented. Analysis showed correlation between solubility and melting point and between melting point of the salt and melting point of the parent acid, but no correlation of salt solubility with solubility of the parent acid. Identification of associations was aided by examining chemically sensible subgroups of the dataset, and this approach highlighted significantly different relationships between solubility and melting point for these subgroups. Thus, for example, the expected negative correlation between solubility and melting point was found for 24 anhydrous benzoate salts, but a positive correlation observed for 8 halide salts. Hydrated forms were anomalous. Packing analysis identified groups of structures that were isostructural with respect to cation packing. Correlation between solubility and melting point was found to be greatest within these isostructural groups, implying a role for packing structure in determining solubility.

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