Crystal structures of (2-substituted-5-N-tosyl)bicyclo[3.3.0]-5-azacyclooct-2-enone: a pseudo achiral crystal from enantiopure compound and a counter-example of Wallach's rule

Kyung Seok Jeong, Dong Eun Kim, Eunsung Lee, Young Ho Jhon, Hogyu Han, Jaheon Kim, Nakcheol Jeong

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An unusual crystallization affording an apparently pseudoachiral crystal from single enantiomers 1a and 1b was observed. In cases of enantiopure molecules such as 1a and 1b with structural flexibility, the tendency toward a centrosymmetric arrangement was so overwhelming that apparently achiral crystals were formed even by homochiral compounds via the formation of a pseudo-centrosymmetric asymmetric unit accompanying structural adjustment. In addition, these crystals of 1a constitute as a counter-example of Wallach's rule.

Original languageEnglish
Pages (from-to)1736-1741
Number of pages6
JournalTetrahedron Asymmetry
Volume20
Issue number15
DOIs
Publication statusPublished - 2009 Aug 12

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this