Thermodynamically controlled synthesis of a chiral tetra-cavitand nanocapsule and mechanism of enantiomerization.

Junling Sun, James L. Bennett, Thomas J. Emge, Ralf Warmuth

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The dynamic covalent synthesis, structure and conformational dynamics of a chiral polyimine nanocapsule 1a are reported. Reaction of four tetraformyl cavitands and eight H2N(CH2)2NH2 yields quantitatively 1a, which has a compact, asymmetrically folded, pseudo-C2-symmetric structure, as determined by X-ray crystallography, and encapsulates four CHCl3 and three CH 3OH guests in the solid state. In solution, 1a enantiomerizes by passing over a barrier of ΔG298 = 21.5 ± 0.7 kcal mol-1 via a refolding process.

Original languageEnglish (US)
Pages (from-to)3268-3271
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number10
DOIs
StatePublished - Mar 16 2011

All Science Journal Classification (ASJC) codes

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

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