Work

A serendipitous synthesis of N,N′-Diethyloxamide: crystallographic and computational analysis of its solid-state structure

Year: 2025

Type: article

Abstract: A combined crystallographic/computational analysis focused on the supramolecular features of the crystal structure of N,N'-diethyloxamide (NNDO) is discussed in this work. The studied compound was obtained unexpectedly during the synthesis of a series of salts of cyclic oximes derivatives. In the solid state NNDO is stabilized essentially through a strong N–H···O hydrogen bond but Hirshfeld surface analysis and Density Functional Theory (DFT) calculations were carried out to evaluate the strength of the predominant hydrogen bonds observed in the X-ray structure, as well as the secondary CH···O and CH···N contacts established between the ethyl groups and the perpendicular dioxamide group. These interactions were further investigated using a combination of Quantum Theory of Atoms in Molecules (QTAIM) and Non-Covalent Interaction Plot (NCIplot) computational tools, and were rationalized using Molecular Electrostatic Potential (MEP) surface calculations.

Source: Chemical Papers

DOI: 10.1007/s11696-025-04428-3

Authors: Mahdi Jemai, Miquel Barceló-Oliver, Houda Marouani, Antonio Frontera, Rafel Prohens

Institutions: University of Carthage, Universitat de Barcelona, Universitat de les Illes Balears

Language: English

Topic: Crystallography and molecular interactions

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,490