Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
New large, up to 45-membered macrocycles were synthesised from piperazine and m- and p-2,6-bis(bromomethyl)xylene under high dilution conditions. X-ray structures of compounds 3a, 4a, 5a, and 8b were determined. Surprisingly, none of the macrocycles prepared showed any inclusion properties towards small guest molecules. Instead, the compounds were found to self-organize during the packing process into larger structures due to the complementary of the molecular skeletons. In the crystalline state 3a forms nets, where the macrocycles are bound by H—C—H…N interactions to each other. 4a exits in a dimeric structure, which, in turn, further extends to a sheet structure. The positively charged phane 8b (di-dihydrochloride salt) adopts a chair-chair conformation, confirming that protonation of the N atoms does not change the conformation.
Type of Medium: