Journal
CHIRALITY
Volume 14, Issue 7, Pages 541-547Publisher
WILEY-LISS
DOI: 10.1002/chir.10080
Keywords
enantiomeric resolution; optical resolution; enantiomeric enrichment; mixed crystal; pseudoracemate; solid solution; X-ray crystallography; crystal structure; melting point phase diagram
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Full characterization of the crystal structures of the racemate, nonracemate (20% ee), and pure enantiomer of [2- [4- (3-ethoxy-2-hydroxypropoxy) phenylcarbamoyl] ethyl] trimethylammonium p-bromobenzenesulfonate (NBMe3), which has successfully shown an unusual enantiomeric resolution phenomenon, preferential enrichment, was achieved by means of X-ray crystallographic analysis and construction of the binary melting point phase diagram. The crystalline nature of the racemate is not a racemic compound but a fairly ordered mixed crystal composed of the two enantiomers. The crystal structure of the nonracemate (20% ee) is virtually identical with that of the racemate and similar to that of the pure enantiomer. The binary melting point phase diagram of NBMe3 is consistent with the nature of a mixed crystal composed of the two enantiomers.
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