Journal of Organic Chemistry p. 3125 - 3132 (1985)
Update date:2022-07-31
Topics:
Weber, Edwin
Josel, Hans-Peter
Puff, Heinrich
Franken, Sybille
A series of organic macrocycles composed of a systematically varied combination of ethano, propano, benzeno, pyridino,and analogous groups, mainly ether-linked (see Chart I), are reported, and their abilities to function as solid-state inclusion hosts are studied.It is found that 3-5, 11-13, 18b, and 21 form crystalline inclusion compounds with a number of low-molecular-weight alcohols such as methanol, ethanol, 1- and 2-propanol, 1-butanol, ethylene glycol, and/or with dimethylformamide and acetonitrile as CH-acidic guests.The observed inclusion selectivities and thestoichiometries of the various host-guest compounds are discussed showing that by and large both chemical and steric host-guest fits apply in the formation of the aggregates.The crystal structure of the inclusion compound of the bipyridino host 11 with 1-propanol (1:1) has been determined from single-crystal X-ray diffraction.There are eight host and guest molecules in each unit cell of dimension a = 2665.2 pm, b = 813.8 pm, c = 2667.4 pm, β = 105.61 deg; space group C2/c; R = 0.088 for 2884 unique reflections.The host macrocycle shows a hollow-type conformation with the 1-propanol molecule coordinated via a moderately stable H-bond to one of the bipyridine nitrogens (O...N = 300 pm).The packing diagram characterizes the host-guest topology largely as a channel-like clathrate (actually "tubulato-coordinatoclathrate").A number of general conclusions that will facilitate the future design of selectively binding hosts for solid-state inclusion are given.
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