Structural basis of solid solution formation during chiral resolution

Orsolya Barabás, Dóra K. Menyhárd, Zsolt Böcskei, Kálmán Simon, Ilona Kiss-Ajzert, Kálmán Takács, I. Hermecz

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A systematic study of crystal packing in a series of structures is presented: an isostructural triplet of an optically active compound {(R)-2-(6,7-diethoxy-1,2,3,4-tetrahydro-1-isoquinolidene)-2-[2-hydroxy-3-(4-morpholinyl)propyl]mercaptoacetonitrile hydrochloride, C22H32ClN3O4S} 1, its racemate 2 and their achiral dehydroxy parent compound {2-(6,7-diethoxy-1,2,3,4-tetrahydro-1-isoquinolidene)-2-[3-(4-morpholinyl)propyl]mercaptoacetonitrile hydrochloride, C22H32ClN3O3S} 3. Based on the structures we suggest some requirements necessary for an optically active compound and its racemate to be isostructural. A generally used resolving agent D-champhor sulphonic acid was unable to provide full separation of the racemate. The crystal structure of a partially resolved product (C32H47N3O8S2) 4 sheds light on the possible reasons of this failure. We suggest a few criteria for solid solution formation of diastereomeric salts. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4061-4070
Number of pages10
JournalTetrahedron Asymmetry
Volume11
Issue number20
DOIs
Publication statusPublished - Oct 20 2000

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Sulfonic Acids
hydrochlorides
Solid solutions
solid solutions
Salts
Crystal structure
Crystals
Acids
sulfonic acid
salts
requirements
crystal structure
products
crystals

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Barabás, O., Menyhárd, D. K., Böcskei, Z., Simon, K., Kiss-Ajzert, I., Takács, K., & Hermecz, I. (2000). Structural basis of solid solution formation during chiral resolution. Tetrahedron Asymmetry, 11(20), 4061-4070. https://doi.org/10.1016/S0957-4166(00)00347-5

Structural basis of solid solution formation during chiral resolution. / Barabás, Orsolya; Menyhárd, Dóra K.; Böcskei, Zsolt; Simon, Kálmán; Kiss-Ajzert, Ilona; Takács, Kálmán; Hermecz, I.

In: Tetrahedron Asymmetry, Vol. 11, No. 20, 20.10.2000, p. 4061-4070.

Research output: Contribution to journalArticle

Barabás, O, Menyhárd, DK, Böcskei, Z, Simon, K, Kiss-Ajzert, I, Takács, K & Hermecz, I 2000, 'Structural basis of solid solution formation during chiral resolution', Tetrahedron Asymmetry, vol. 11, no. 20, pp. 4061-4070. https://doi.org/10.1016/S0957-4166(00)00347-5
Barabás O, Menyhárd DK, Böcskei Z, Simon K, Kiss-Ajzert I, Takács K et al. Structural basis of solid solution formation during chiral resolution. Tetrahedron Asymmetry. 2000 Oct 20;11(20):4061-4070. https://doi.org/10.1016/S0957-4166(00)00347-5
Barabás, Orsolya ; Menyhárd, Dóra K. ; Böcskei, Zsolt ; Simon, Kálmán ; Kiss-Ajzert, Ilona ; Takács, Kálmán ; Hermecz, I. / Structural basis of solid solution formation during chiral resolution. In: Tetrahedron Asymmetry. 2000 ; Vol. 11, No. 20. pp. 4061-4070.
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