Hexaaza and octaaza macrocycles with 2-hydroxy-3,5-dimethylbenzyl pendant arms
Author(s)
Author(s)
Choi, N.
Evagorou, E. G.
McPartlin, M.
Date Issued
1997
Publisher
Royal Society of Chemistry
Journal
Journal of the Chemical Society, Perkin Transactions 1
Issue
21
Start page
3151
End page
3156
Abstract
New 18-membered hexaaza (3 and 4) and 24-membered octaaza (7 and 8) macrocycles with 2-hydroxy-3,5-dimethylbenzyl pendant arms have been prepared via a Mannich type reaction of the corresponding macrocycles [(1 and 2) and (5 and 6) respectively] with 2,4-dimethylphenol in the presence of methanal in a methanolic solution. X-Ray structure analysis shows the tetramethyl substituted hexaaza macrocycle with 2-hydroxy-3,5-dimethylbenzyl pendant arms 4 and its precursor [H42]4+ both have centrosymmetric molecules with step conformation. Differences in conformation arise from hydrogen bonding interactions; in [H42]4+ bonding between amino nitrogen atoms and water molecules appears to tie the backbone chain of the macrocycle together, and in 4 strong intramolecular hydrogen bonding with each 2-hydroxybenzylamino unit dictates the orientation of the pendant arms.
SFU Affiliated Publication
No
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