Hydrogen Bonded Ladder Structures

School of Chemistry, University of New South Wales
â—‹Roger - Bishop Vi T. Nguyen Isa Y. Chan Donald C. Craig Marcia L. Scudder

Certain dialcohols crystallize by means of hydrogen bonding into two parallel strands that are cross-linked by additional hydrogen bonding to form self-assembling ladder structures. If the strands are cross-linked in phase with each other then a step-ladder arrangement is produced. However, if they are cross-linked out-of-phase, then a twisted staircase-ladder results.

There is a strong preference for staircase ladders to contain only one dialcohol enantiomer, even if the starting material is racemic. This paper will describe a new dialcohol capable of forming at least five different staircase-ladder arrangements whose assembly is determined simply by the crystallization conditions employed.
V.T. Nguyen, P.D. Ahn, R. Bishop, M.L. Scudder and D.C. Craig, Eur. J. Org. Chem., 4489 (2001).