TY - JOUR
T1 - The bicyclic N,N′-diacylaminal
T2 - A new motif for molecular self-assembly
AU - Grossman, Robert B.
AU - Hattori, Kazuyuki
AU - Parkin, Sean
AU - Patrick, Brian O.
AU - Varner, Melissa A.
PY - 2002/11/20
Y1 - 2002/11/20
N2 - 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 R22(8)-type 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.
AB - 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 R22(8)-type 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.
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U2 - 10.1021/ja026949y
DO - 10.1021/ja026949y
M3 - Article
C2 - 12431093
AN - SCOPUS:0037146003
SN - 0002-7863
VL - 124
SP - 13686
EP - 13687
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -