Control of Hydrogen Bonding in the Design of New Diol Lattice Inclusion Compounds

Abstract In order to be able to predict and then synthesize new lattice inclusion compounds with the helical tubuland diol host structure, the hydrogen bonding modes of a range of bicyclic and tricyclic diols have been studied using X-ray crystallography. Several distinct types of lattice structure have been recognized. Steric factors play a major role in determining which of these is produced in a given case. Establishment of a series of structural rules provides a window of opportunity for duplication of the helical tubuland host lattice by deliberate design and synthesis. New inclusion compounds resulting from this approach are presented.

[1]  A. Gavezzotti,et al.  Generation of possible crystal structures from molecular structure for low-polarity organic compounds , 1991 .

[2]  I. Goldberg.  The Significance of Molecular Type, Shape and Complementarity in Clathrate Inclusion , 1988, Molecular Inclusion and Molecular Recognition – Clathrates II.

[3]  E. Weber,et al.  A proposal for the classification and nomenclature of host-guest-type compounds , 1983 .

[4]  I. Dance,et al.  Crystal structures of helical tubulate inclusion compounds formed by 2,6-dimethylbicyclo[3.3.1]nonane-exo-2,exo-6-diol , 1992 .

[5]  I. Dance,et al.  2,6-Dimethylbicyclo(3.3.1)nona-3,7-diene-endo-2,endo-6-diol, an Alicyclic Diol Whose Crystal-Structure Involves Two Types of Hydrogen-Bonded Columns , 1991 .

[6]  S. Hawkins,et al.  Syntheses and crystal structures of seven alicyclic diols which crystallise with layer structures instead of the helical tubuland inclusion lattice , 1990 .

[7]  D. Craig,et al.  Preparation and crystal structure of a twin twist-boat bicyclo[3.3.1]nonane monohydrate , 1989 .

[8]  S. Hawkins,et al.  Modification of tube size and shape in a helical tubuland inclusion lattice formed by a new family of diol hosts: syntheses and crystal structures , 1986 .

[9]  I. Dance,et al.  Different crystal structures of inclusion complexes formed by syn-2,syn-7-dihydroxy-2,7-dimethyltricyclo[4.3.1.13,8]undecane with ethyl acetate and benzene , 1983 .

[10]  Jean Jacques,et al.  Enantiomers, Racemates, and Resolutions , 1981 .

[11]  Aleksandr Isaakovich Kitaĭgorodskiĭ,et al.  Molecular Crystals and Molecules , 1973 .