Issue 6, 2002
From the journal:

New Journal of Chemistry

Carbocyclic molecular clefts incorporating hydrogen bonding features

Jeremy D. Field,a   Peter Turner,a   Margaret M. Harding,*a   Theano Hatzikominosa  and  Linda Kima  

* Corresponding authors

a School of Chemistry, The University of Sydney, Sydney, Australia
E-mail: harding@chem.usyd.edu.au

Abstract

Chiral carbocyclic cleft molecules incorporating carbonyl, hydroxy, oxime, o-phenol and m-nitroaryl groups have been synthesised from dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione, a carbocyclic analogue of Tröger's base. These clefts contain similar features to Tröger's base but in addition contain carbonyl groups, which are readily modified, on the chiral bridge that forms the molecular cleft. The oxime and m-nitroaryl derivatives have been characterised by single crystal X-ray diffraction. The dihedral angles between the two aromatic rings of these two molecules and those of previously reported related molecules are compared. Two crystal packing motifs are identified and found to influence the size of the dihedral cleft angle of this type of molecule.

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Article information

DOI
https://doi.org/10.1039/B109055K
Article type
Paper
Submitted
05 Oct 2001
Accepted
05 Feb 2002
First published
27 May 2002

New J. Chem., 2002,26, 720-725

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Carbocyclic molecular clefts incorporating hydrogen bonding features

J. D. Field, P. Turner, M. M. Harding, T. Hatzikominos and L. Kim, New J. Chem., 2002, 26, 720 DOI: 10.1039/B109055K

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