Two novel long chain aziridinemethanols (1b, c) are described and their mol
ecular organisation in the bulk and self-assembling properties in aqueous d
ispersion are reported. The orientation of the NH hydrogen of the aziridine
alcohol moiety in 1b can be changed by introducing a methyl substituent int
o the rigid three-membered ring, leading to a change in the hydrogen bondin
g pattern interconnecting these molecules. This change in configuration lea
ds to marked differences in the ordering of these molecules in the solid st
ate. Although compounds 1b and 1c both form highly organised structures in
aqueous media and on the air-water interface, noteworthy differences are ob
served. Compound 1c yields left-handed helical ribbons whereas no chiral ag
gregates are found for 1b. However, the addition of 2-acetoxybenzoic acid (
aspirin) to an aqueous dispersion of 1b leads to the generation of both lef
t- and right-handed helical structures. Under these conditions a reaction h
ad taken place that was specific for the ortho-isomer of acetoxybenzoic aci
d.