Wydział Chemii

Hamideh Ahankar

Ali Ramazani

Hamid Saeidian

Katarzyna Ślepokura

Tadeusz Lis

2021

Journal of Structural Chemistry

62

47-57

10.1134/s0022476621010066

Naukowa

Angielski

Artykuł

An efficient method for the synthesis of a new highly substituted pyrrolidinone derivative is developed via a three-component one-pot reaction of aniline, diethyl acetylenedicarboxylate, and 4-anisaldehyde. The structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate is confirmed by FTIR, ¹H and ¹³C NMR spectroscopy. Unambiguous evidence for the structure of the synthesized product is obtained from the single crystal X-ray analysis. The comparison of both its molecular structure and intermolecular interactions with the previously known analogous compounds reveals that the mutual syn- or antiperiplanar orientation of ester C=O and pyrrolinone-bound OH is related to the type of molecular dimers formed in the solid state. The geometrical structure, the HOMO–LUMO analysis (electrophilicity index), ¹H and ¹³C chemical shifts of the desired product are also calculated by DFT at the B3LYP level with the 6-31++G(d,p) basis set. The calculated chemical shifts are in compliance with the experimental data.

pyrrolidinone derivative, multicomponent reaction, single crystal X-ray analysis, density functional theory, electrophilicity index

http://dx.doi.org/10.1134/S0022476621010066