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Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

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Date
2020-05-08
Author
Arango, Alejandra M.
Wist, Julien
Ellena, Javier Alcides
D'vries Arturo, Richard Fernando
Chaur, Manuel N.
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Abstract
We employed (Z)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]nicotinohydrazide (2) and (Z)‐4‐(dimethylamino)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]benzohydrazide (3) as cores of dynamic chemical systems whose different states are modulated, in a reversible fashion, through specific physical and chemical stimuli. The structure of the compounds was determined by Nuclear Magnetic Resonance (NMR) techniques (1D and 2D) and confirmed by single‐crystal X‐ray diffraction. By Variable temperature (VT) 1H NMR experiments and DFT calculations, the conformational isomerism of 2 was studied and added as an additional input for the dynamic system. Additionally, 2 exhibits configurational E/Z isomerization mediated by pH variations and UV light. On the other hand, configurational isomerism locks an unlocks a tridentate pocket for metal cation coordination in both 2 and 3. All the different dynamic states configurational/conformational isomerism and locked and unlocked coordination constitute a development in the field of systems of multiple dynamics suitable for molecular machines.
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http://repository.usc.edu.co/handle/20.500.12421/4530
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