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Issue 21, 2020
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The eternal battle to combat global warming: (thio)urea as a CO2 wet scrubbing agent

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Abstract

(Thio)Urea scaffolds are best known for their importance as intermediates in organic synthesis. In this work, a mechanistic study of the reaction between urea (U), (2-hydroxyethyl)urea (U-EtOH) and thiourea (tU)/NaH in DMSO with CO2 was carried out. While both U/tU reacted with CO2via a 1 : 2 mechanism through the formation of the keto (thio)carbamide–carboxylate adducts (k-U/tU-CO2 Na+), U-EtOH gave mixed CO2-adducts composed of organic carbonate and carbamide–carboxylate moieties (Na+-CO2-U-Et-OCO2 Na+). Moreover, we recorded for the first time, a new type of bond, namely sodium carbamimidothiocarbonate (e-tU-SCO2 Na+), upon bubbling CO2 in the DMSO solution of tU due to the persistence of the enol form (e-tU) and the better nucleophilicity of sulfur over nitrogen focal points. The reaction mechanisms were proven by 1D and 2D nuclear magnetic resonance (NMR) and ex situ attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopies. The stability of these bonds was studied following the changes in 1H-NMR as a function of temperature, which indicated the reversibility of these reactions. Furthermore, the proposed mechanisms were explored theoretically via density functional theory (DFT) calculations by analyzing the energetics of the anticipated products.

Graphical abstract: The eternal battle to combat global warming: (thio)urea as a CO2 wet scrubbing agent

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Supplementary files

Article information


Submitted
04 Feb 2020
Accepted
23 Apr 2020
First published
24 Apr 2020

Phys. Chem. Chem. Phys., 2020,22, 11829-11837
Article type
Paper

The eternal battle to combat global warming: (thio)urea as a CO2 wet scrubbing agent

A. F. Eftaiha, A. K. Qaroush, A. W. Alsayyed, F. Al-Qaisi, F. Alsoubani and K. I. Assaf, Phys. Chem. Chem. Phys., 2020, 22, 11829
DOI: 10.1039/D0CP00629G

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