The hydrochloride and hydrobromide salt forms of (S)-amphetamine

Lynn Dennany, Alan R. Kennedy, Brandon Walker

Research output: Contribution to journalArticle

Abstract

(S)-Amphetamine hydrochloride, C9H14ClN, has a Z′ = 6 structure with six independent cation, anion pairs. That these are indeed crystallographically independent is supported by different packing orientations of the cations and by observation of a wide range of cation conformations generated by rotation about the phenyl–CH2 bond. The supramolecular contacts about the anions also differ such that both a wide variation in the geometry of the three N–H···Cl hydrogen bonds formed by each chloride anion and differences in C–H···Cl contacts are apparent. (S)-Amphetamine hydrobromide, C9H14BrN, is broadly similar to the chloride in terms of cation conformation, the existance of three N–H···X hydrogen bond contacts per anion and the overall 2 dimensional hydrogen bonded sheet motif. However, only the chloride structure features organic bilayers and Z′ > 1.
LanguageEnglish
Pages844-849
Number of pages6
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume71
Issue number10
DOIs
Publication statusAccepted/In press - 25 Aug 2015

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Amphetamine
Anions
Cations
Salts
Chlorides
Hydrogen
Conformations
Hydrogen bonds
Geometry

Keywords

  • (S)-Amphetamine hydrochloride
  • phenylethylamine salts
  • crystal structures

Cite this

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The hydrochloride and hydrobromide salt forms of (S)-amphetamine. / Dennany, Lynn; Kennedy, Alan R.; Walker, Brandon.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 71, No. 10, 25.08.2015, p. 844-849.

Research output: Contribution to journalArticle

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AB - (S)-Amphetamine hydrochloride, C9H14ClN, has a Z′ = 6 structure with six independent cation, anion pairs. That these are indeed crystallographically independent is supported by different packing orientations of the cations and by observation of a wide range of cation conformations generated by rotation about the phenyl–CH2 bond. The supramolecular contacts about the anions also differ such that both a wide variation in the geometry of the three N–H···Cl hydrogen bonds formed by each chloride anion and differences in C–H···Cl contacts are apparent. (S)-Amphetamine hydrobromide, C9H14BrN, is broadly similar to the chloride in terms of cation conformation, the existance of three N–H···X hydrogen bond contacts per anion and the overall 2 dimensional hydrogen bonded sheet motif. However, only the chloride structure features organic bilayers and Z′ > 1.

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