Issue 7, 2022

The crystal structure and characterization of a co-product in the synthesis of a Schiff base give evidence of its zwitterionic nature in the solid state

Abstract

During the synthesis of the Schiff base 2-methoxy-6-{[(tiophen-2-methyl)imino]methyl}phenol (o-HVATPNH2), a co-product was isolated and characterized. The crystal structure of this molecule, 4,10-dimethoxy-13-(thiophen-2-ylmethyl)-6,12-dihydro-6,12-epiminodibenzo[b,f][1,5]dioxocane, namely (o-VA)2TPNH2 for short, was determined by X-ray diffraction methods. The chiral compound crystallizes as a racemate in the triclinic space group P[1 with combining macron] with 2 molecules per unit cell. The (o-VA)2 molecular fragment in (o-VA)2TPNH2 shows a non-crystallographic two-fold axis that enables the two molecular stereogenic centers to have the same chirality. The formation reaction mechanism for (o-VA)2TPNH2 is proposed and the structural properties of the Schiff base o-HVATPNH2 were revised. Evidence of the presence of the zwitterionic form of a Schiff base in the solid state was found.

Graphical abstract: The crystal structure and characterization of a co-product in the synthesis of a Schiff base give evidence of its zwitterionic nature in the solid state

Supplementary files

Article information

Article type
Paper
Submitted
21 Sep 2021
Accepted
27 Dec 2021
First published
27 Dec 2021

New J. Chem., 2022,46, 3130-3139

The crystal structure and characterization of a co-product in the synthesis of a Schiff base give evidence of its zwitterionic nature in the solid state

M. R. Rodríguez, G. A. Espino, O. E. Piro, G. A. Echeverría, B. S. Parajón-Costa and A. C. González-Baró, New J. Chem., 2022, 46, 3130 DOI: 10.1039/D1NJ04537G

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