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Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones.

ABSTRACT: Substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones have been prepared via three-component reactions and the tautomerism of these 3-pyrroline-2-ones is due to the slight difference of energy, and the significantly large rate constant of transformation between two tautomers. 1,4,5-Trisubstituted pyrrolidine-2,3-dione derivatives were prepared from the above mentioned 2-pyrrolidinone derivatives and aliphatic amines, which exist in enamine form and are stabilized by an intramolecular hydrogen bond. A possible reaction mechanism between 3-pyrroline-2-one and aliphatic amine (CH₃NH₂) was proposed based on computational results and the main product is formed favorably following the PES via the lowest ΔG ^# pathway in both the gas-phase and an ethanol solvent model. DFT calculations showed that kinetic selectivity is more significant than thermodynamic selectivity for forming main products.

SUBMITTER: Nguyen NT

PROVIDER: S-EPMC9443309 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones.

Nguyen Nguyen Tran NT Dai Vo Viet VV Tri Nguyen Ngoc NN Van Meervelt Luc L Trung Nguyen Tien NT Dehaen Wim W

Beilstein journal of organic chemistry 20220831

Substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones have been prepared via three-component reactions and the tautomerism of these 3-pyrroline-2-ones is due to the slight difference of energy, and the significantly large rate constant of transformation between two tautomers. 1,4,5-Trisubstituted pyrrolidine-2,3-dione derivatives were prepared from the above mentioned 2-pyrrolidinone derivatives and aliphatic amines, which exist in enamine form and are stabilized by an intramolecular hydrogen bond. ...[more]

PMID: 36105726

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Project description:Gold nanoparticles depending on their shape and mixtures of multiple shapes can exhibit peculiar optical properties, including the dichroic effect typical of the Lycurgus cup, which has puzzled scientists for a long time. Such optical properties have been recently exploited in several fields such as paint technology, sensors, dichroic polarizers, display (LCD) devices, laser applications, solar cells and photothermal therapy among others. In this article, we have demonstrated a simple room temperature one-pot synthesis of gold sol displaying a dichroic effect using a slow reduction protocol involving only trisodium citrate as a reducing agent. We found that the dichroic gold sol can be easily formed at room temperature by reducing gold salt by trisodium citrate below a certain critical concentration. The sol displayed an orangish-brown color in scattered/reflected light and violet/blue/indigo/purple/red/pink in transmitted light, depending on the experimental conditions. With minor changes such as the introduction of a third molecule or replacing a small amount of water in the reaction mixture with ethanol, the color of the gold sol under transmitted light changed and a variety of shades of red, pink, cobalt blue, violet, magenta and purple were obtained. The main advantage of the proposed method lies in its simplicity, which involves the identification of the right ratio of the reactants, and simple mixing of reactants at room temperature with no other requirements. TEM micrographs displayed the formation of two main types of particles viz. single crystal gold nanoplates and polycrystalline faceted polyhedron nanoparticles. The mechanism of growth of the nanoplates and faceted polyhedron particles have been described by an enhanced diffusion limited aggregation numerical scheme, where it was assumed that both trisodium citrate and the gold ions in solution undergo a stochastic Brownian motion, and that the evolution of the entire system is regulated by a principle of energy minimization. The predictions of the model matched with the experiments with a good accuracy, indicating that the initial hypothesis is correct.

Dataset Information

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones.

Publications

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones.

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