The bicyclic n,n'-diacylaminal: a new motif for molecular self-assembly.
A cage-shaped N,N'-diacylaminal crystallizes from some aromatic solvents as "supramolecular chair cyclohexanes", squat cylindrical hexamers with approximate D3d symmetry containing two arene molecules, and from other aromatic and nonaromatic solvents as infinite tapes. A homologous diacylaminal crystallizes only as an infinite tape. The hexamers represent the first examples of cyclic hexamers held together by %@mt;sys@%%@bold@%R%@rsf@%%@sx@%2%@be@%2%@sxx@%%@fn;(;vis;full;auto@%8%@fnx;);vis;full@%-type%@mx@% hydrogen bonds in which the hydrogen-bonded atoms are not coplanar. The diacylaminal represents a new supramolecular synthon, one perhaps more suited to the design of three-dimensional architectures.
Grossman
Robert B
RB
Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055, USA. rbgros1@uky.edu
Hattori
Kazuyuki
K
Parkin
Sean
S
Patrick
Brian O
BO
Varner
Melissa A
MA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D008958:Models, Molecular
D019086:Bridged Bicyclo Compounds, Heterocyclic; D046911:Macromolecular Substances