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

Abstract : 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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Soumis le : mardi 3 septembre 2019 - 10:05:44
Dernière modification le : jeudi 24 octobre 2019 - 15:32:07

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Ryusei Oketani, Hiroki Takahashi, Marine Hoquante, Clément Brandel, Pascal Cardinaël, et al.. NH-form of a threonine-based Schiff base in the solid state. Journal of Molecular Structure, Elsevier, 2019, 1184, pp.36-40. ⟨10.1016/j.molstruc.2019.01.093⟩. ⟨hal-02081050⟩

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