Title | Hexaaza and octaaza macrocycles with 2-hydroxy 3,5-dimethylbenzyl pendant arms |
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Authors | Bligh, S.W.A., Choi, N., Evagorou, E.G. and McPartlin, M. |
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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. |
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Journal | Journal of the Chemical Society, Perkin Transactions |
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Journal citation | 1997 (21), pp. 3151-3156 |
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ISSN | 1472-7781 |
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Year | 1997 |
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Publisher | Royal Society of Chemistry |
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Digital Object Identifier (DOI) | https://doi.org/10.1039/A704835A |
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Publication dates |
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Published | 1997 |
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