Green synthesis of N,N′-(1,2-phenylene)bis(phthalimide-5-carboxilic acid) and the prediction of its properties: Standard enthalpies of formation and sublimation
Year: 2025
Type: article
Abstract: The synthesis of the molecule N,N′-(1,2-phenylene)bis(phthalimide-5-carboxylic acid) was carried out using green chemistry principles. The reactants 1,2-diaminobenzene and 1,2,4-benzenetricarboxylic anhydride were used for solid-state synthesis without catalysts. The resulting compound called oDIDA was characterized using infrared spectroscopy, mass spectrometry, proton nuclear magnetic resonance, and differential scanning calorimetry. Experimentally it was possible to obtain the structure, composition and melting temperature at 546.46 K. Since the compound oDIDA decomposes upon reaching its melting point, its thermochemical properties were predicted in the gaseous and crystalline phases. Ab initio molecular orbital calculations at the B3LYP/6-311++G(d,p) level of theory were occupied to determine the gaseous-phase heat capacities and absolute entropies. Supervised learning was applied to a dataset of carboxylic acids and imides to predict the standard molar enthalpies of formation and sublimation using the hold-out (70/30) evaluation technique. Finally, enthalpic increases, relative stabilities and the analysis of equilibrium reaction for the synthesis of oDIDA were obtained.
Source: Journal of Molecular Structure
Institution: Benemérita Universidad Autónoma de Puebla
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,360
Awards: G8066980823, G8118645892
OpenAlex ID: W4410477066