|Title||Hexaaza and octaaza macrocycles with 2-hydroxy 3,5-dimethylbenzyl pendant arms|
|Authors||Bligh, S.W.A., Choi, N., Evagorou, E.G. and McPartlin, M.|
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.
|Journal||Journal of the Chemical Society, Perkin Transactions|
|Journal citation||1997 (21), pp. 3151-3156|
|Publisher||Royal Society of Chemistry|
|Digital Object Identifier (DOI)||https://doi.org/10.1039/A704835A|