What is it about?
By taking advantage of 1D NMR (1H and 13C NMR) and 2D NMR (NOESY) spectroscopic analyses of NMR data in dissolved DMSO-d6 at room tempertaure, we indicated the presence of acetohydrazine derivatives as a mixture of two conformers. The critical parameter is a slow rotation around the N-acyl bond, with the N-H bond being in a cis or trans position with respect to the carbonyl bond, leading respectively to syn-periplanar E (sp E) or anti-periplanar E (ap E) conformers.
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Why is it important?
The work deals with the synthesis of a series of heteroaromatic compounds including a particular functional group, N-acyl hydrazone that is subject to dynamic isomerism, a phenomenon that the work identifies, thanks to the NMR tool. Despite the effect of temperature on this equilibrium position, mainly in DMSO, considering its boiling point. A variable temperature NMR experiment was done but the coalescence and the activation barrier of the conformational equilibrium did not show any difference from what we found as results.
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This page is a summary of: Synthesis and characterization of novel conformers of (
E
)
‐
2‐(3‐nitro‐
H
‐imidazo[1,2‐
a
]pyridin‐2‐ylthio)‐
N..., Magnetic Resonance in Chemistry, September 2022, Wiley,
DOI: 10.1002/mrc.5308.
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