Novel O-C-C-O and C-O-C-C stereochemistry in crown ether analogs. X-ray crystal structure and NMR studies of dibenzo-20-crown-6

The X-ray crystal structure of the title material indicates that the molecule possesses a pseudo-centre of inversion. A pair of O-C-C-O bonds have a trans conformation in contrast to normal gauche stereochemistry for such units in crown ethers. For the C-O-C-C networks, which are normally transoid i...

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Bibliographic Details
Published in:Canadian journal of chemistry 1995-01, Vol.73 (1), p.100-105
Main Authors: Buchanan, G.W, Moghimi, A, Bensimon, C
Format: Article
Language:English
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Summary:The X-ray crystal structure of the title material indicates that the molecule possesses a pseudo-centre of inversion. A pair of O-C-C-O bonds have a trans conformation in contrast to normal gauche stereochemistry for such units in crown ethers. For the C-O-C-C networks, which are normally transoid in crown ethers, all four such units involving methylene carbons of the 20-membered ring exhibit unusual geometries. Two units possess gauche conformations and the other two have torsion angles near 120°. Solution 1 H and 13 C NMR spectra have been recorded as a function of temperature and 13 C solid state spectra are included. Keywords: crown ether, solid state conformation.
ISSN:0008-4042
1480-3291
DOI:10.1139/v95-015