Dataset Information

CS₂/CO₂ Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study.

ABSTRACT: We report on the reaction of ethylene-terminated heteroatoms (C₂X; X = N, O, and S) with CS₂/CO₂ using Mukaiyama reagent (2-chloro-1-methylpyridinium iodide, CMPI) as a promoter for the preparation of imidazolidin-2-one, oxazolidin-2-one, 1,3-dioxolan-2-one, 1,3-dithiolan-2-one, and their thione counterparts at ambient temperature and pressure. Spectroscopic measurements, viz., ¹H/¹³C nuclear magnetic resonance (NMR) and ex situ attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy methods verified the reaction of CS₂/CO₂ with the ethylene-based substrates and subsequently the formation of cyclic products. The experimental data indicated the formation of the enol-form of imidazolidin-2-one and oxazolidin-2-one, while the keto-form was obtained for their thione correspondents. Furthermore, density functional theory calculations revealed the stability of the keto- over the enol-form for all reactions and pointed out the solvent effect in stabilizing the latter.

SUBMITTER: Qaroush AK

PROVIDER: S-EPMC9260919 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Publications

CS2/CO2 Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study.

Qaroush Abdussalam K AK Eftaiha Ala'a F AF Smadi Amneh H AH Assaf Khaleel I KI Al-Qaisi Feda'a M FM Alsoubani Fatima F

ACS omega 20220621 26

We report on the reaction of ethylene-terminated heteroatoms (C2X; X = N, O, and S) with CS2/CO2 using Mukaiyama reagent (2-chloro-1-methylpyridinium iodide, CMPI) as a promoter for the preparation of imidazolidin-2-one, oxazolidin-2-one, 1,3-dioxolan-2-one, 1,3-dithiolan-2-one, and their thione counterparts at ambient temperature and pressure. Spectroscopic measurements, viz., 1H/13C nuclear magnetic resonance (NMR) and ex situ</i ...[more]

PMID: 35811893

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Project description:The consumption of contaminated shellfish with marine toxins causes adverse socioeconomical, environmental and health impacts. The marine toxin okadaic acid (OA) provokes diarrhetic shellfish poisoning (DSP) syndrome characterized by severe gastrointestinal symptoms. Therefore, there is increasing interest in removing these toxins from the marine environment to protect shellfish harvesting sites. Photocatalysis is proposed as an efficient method to detoxify the marine environment. In this study, Prorocentrum lima was used to produce high purity DSP toxins, in particular OA, for degradation studies. The profiling, characterization and quantification of DSP toxins in the culture of P. lima were achieved by ultrahigh performance liquid chromatography coupled to quadrupole-time of flight mass spectrometry (UPLC-QTOF-MSE) for accurate-mass full spectrum acquisition data. The effectiveness of UV/TiO2 system to degrade OA in seawater was assessed in lab-scale experiments and identification of transformation products was proposed based on the data obtained during analysis by UPLC-QTOF-MSE. The detoxification potential of the UV/TiO2 system was investigated using the phosphatase inhibition assay. Sufficient amount of high-purity OA (25 mg, >90% purity) was produced in-house for use in photocatalysis experiments by simple reversed-phase flash chromatography. Complete degradation of OA was observed in seawater after 30 min and 7.5 min in deionized water. The rate constants fitted with the pseudo-first order kinetic model (R2 > 0.96). High-resolution mass spectrometry analysis of the photocatalyzed OA allowed tentative identification of four transformation products. Detoxification was achieved in parallel with the degradation of OA in deionized water and artificial ocean water (≤20 min) but not for seawater. Overall, results suggest that UV/TiO2 photocatalysis can be an effective approach for degrading OA and their TPs in the marine environment. To the best of our knowledge, this is the first report on the use of photocatalysis to degrade marine toxins and its promising potential to protect shellfish harvesting sites.

Dataset Information

CS₂/CO₂ Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study.

Publications

CS<sub>2</sub>/CO<sub>2</sub> Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study.

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