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

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

doi:10.1021/ja110475w

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

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

School of Arts and Sciences, Chemistry & Chemical Biology

Research output: Contribution to journal › Article › peer-review

32 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 language	English (US)
Pages (from-to)	3268-3271
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	10
DOIs	https://doi.org/10.1021/ja110475w
State	Published - Mar 16 2011

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Thermodynamically controlled synthesis of a chiral tetra-cavitand nanocapsule and mechanism of enantiomerization.",

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.",

author = "Junling Sun and Bennett, {James L.} and Emge, {Thomas J.} and Ralf Warmuth",

year = "2011",

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AU - Sun, Junling

AU - Bennett, James L.

AU - Emge, Thomas J.

AU - Warmuth, Ralf

PY - 2011/3/16

Y1 - 2011/3/16

N2 - 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.

AB - 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.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

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

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