Chiral symmetry breaking in stirred crystallization of 1,1'-binaphthyl melt

Dilip K. Kondepudi, Jennifer Laudadio, Kouichi Asakura

Research output: Contribution to journalArticle

159 Citations (Scopus)

Abstract

As a supercooled melt at 150°C, the chiral compound 1,1'-binaphthyl racemizes rapidly. The melt solidifies as a conglomerate of crystals, each consisting exclusively of either R-(-)- or S-(+)-enantiomer. We find that crystallization performed with a 2.00 g sample with constant stirring produces a large enantiomeric excess (mean 77%) in almost every crystallization. The predominance of R-(-) or S-(+) was random. Unstirred 2.00 g samples of binaphthyl produce a much lower enantiomeric excess (mean 20%) with optical activity centered around zero similar to an earlier report. Thus, chiral symmetry breaking can be realized in crystallization from a melt by the mere act of stirring, as it can be in crystallization from a solution.

Original languageEnglish
Pages (from-to)1448-1451
Number of pages4
JournalJournal of the American Chemical Society
Volume121
Issue number7
DOIs
Publication statusPublished - 1999 Feb 24

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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