NH-form of a threonine-based Schiff base in the solid state

Add time:07/31/2019    Source:sciencedirect.com

Stable NH-form of the threonine-based Schiff base 4, (2S,3R)-3-((tert-butyldimethylsilyl)oxy)-2-(((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)butanamide, was synthesized and characterized in the crystalline state by means of IR spectroscopy and X-ray crystallographic analysis. This is the first X-ray determination of an amino acid-based Schiff base that was locked in the NH-form. Comparison of the characteristic bond lengths based on the X-ray structure of 4 with previously reported NH-forms of other Schiff bases revealed that the structure of 4 was a hybrid of two canonical structures, namely, zwitterion and quinoid, contributing to the resonance. It was also found that 4 exist in the OH-form in solution and its phenolic proton is well-constrained via intramolecular hydrogen bonding with the imine functionality.

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