Anca Gabriela Mirea (National Institute of Materials Physics, Romania)
Abstract: We present herein the synthesis of novel [2 + 2] and [3 + 3] N-acylhydrazone-based macrocycles using a pool of dialdehydes and dihydrazides. The macrocycles were used in various assays to investigate the hosting capacity of various guests using NMR.
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Hi Anca, interesting work! Could you please elaborate a bit more on how you inferred the triangular or tetragonal geometry using 2D NMR?
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Hy Amit! To elucidate the macrocyclic shape, we recorded 2D NMR (NOESY) indicating a triangular shape, according to the space interactions of protons within the molecule. The spectrum revealed NOE connectivity between NH and H (hydrazide moieties) protons, as well as CH=N and H (aldehyde moieties) protons. For more details you can read our article DOI: 10.1039/d4ta09035g.
Thank you very much for your interest! I appreciate your question!
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Hy Amit! To elucidate the macrocyclic shape, we recorded 2D NMR (NOESY) indicating a triangular shape, according to the space interactions of protons within the molecule. The spectrum revealed NOE connectivity between NH and H (hydrazide moieties) protons, as well as CH=N and H (aldehyde moieties) protons. For more details you can read our article DOI: 10.1039/d4ta09035g.
Thank you very much for your interest! I appreciate your question!
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Thanks Anca.
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Nice work Anca – why do you think the rectangular macrocycle readily took up F- and not Br-? What about Cl-? From your work, do you have any insights on what kind of synthetic considerations give rise to different macrocycle shapes?
Thanks!-
Hy Riley! The interaction of the rectangular macrocycle with TBAF may either lead to deprotonation of the hydroxyl and amide groups or cause
hydrogen bonding between the fluoride and the two groups.
The shape of the macrocycle depends on the precursors used for the synthesis.Thank you very much for your interest! I appreciate your question!
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