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

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Crystal counters
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Crystal structure
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crystal structure
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Enantiomers
enantiomers
Crystallization
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tendencies
adjusting
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Molecules
molecules

ASJC Scopus subject areas

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

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

In: Tetrahedron Asymmetry, Vol. 20, No. 15, 12.08.2009, p. 1736-1741.

Research output: Contribution to journalArticle

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