Computational predictions on Brønsted acidic ionic liquid-catalyzed carbon dioxide conversion to five-membered heterocyclic carbonyl derivatives

Abdullayev, Yusif; Karimova, Nazani; Schenberg, Leonardo A.; Ducati, Lucas C.; Autschbach, Jochen

doi:10.1039/d2cp05877d

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“…15 Despite the economical and efficient transformations of 2Cl-VD synthon into versatile heterocyclic organic compounds, as stated above, the 2Cl-VD synthesis reaction mechanism has so far not been investigated theoretically, even though calculations are frequently applied to scrutinize reaction mechanisms. [18][19][20][21][22][23][24][25] TMEDA and other related diamine species have been frequently exploited previously as ligands for stabilizing copper complexes. 26,27 Lumb et al studied copper (I) and some diamine (N,N 0 -di-tert-butylethylenediamine, p-(N,N-dimethylamino)pyridine, etc.)…”

Section: Introductionmentioning

confidence: 99%

Computational exploration of the copper(I)‐catalyzed conversion of hydrazones to dihalogenated vinyldiazene derivatives

Askerova,

Abdullayev,

Shikhaliyev

et al. 2024

J Comput Chem

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This computational study explores the copper (I) chloride catalyzed synthesis of (E)‐1‐(2,2‐dichloro‐1‐phenylvinyl)‐2‐phenyldiazene (2Cl‐VD) from readily available hydrazone derivative and carbon tetrachloride (CCl4). 2Cl‐VD has been extensively utilized to synthesize variety of heterocyclic organic compounds in mild conditions. The present computational investigations primarily focus on understanding the role of copper (I) and N1,N1,N2,N2‐tetramethylethane‐1,2‐diamine (TMEDA) in this reaction, TMEDA often being considered a proton scavenger by experimentalists. Considering TMEDA as a ligand significantly alters the energy barrier. In fact, it is only 8.3 kcal/mol higher compared to the ligand‐free (LF) route for the removal of a chlorine atom to form the radical ·CCl3 but the following steps are almost barrierless. This intermediate then participates in attacking the electrophilic carbon in the hydrazone. Crucially, the study reveals that the overall potential energy surface is thermodynamically favorable, and the theoretical turnover frequency (TOF) value is higher in the case of Cu(I)‐TMEDA complex catalyzed pathway.

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Section: Introductionmentioning

confidence: 99%

Computational exploration of the copper(I)‐catalyzed conversion of hydrazones to dihalogenated vinyldiazene derivatives

Askerova,

Abdullayev,

Shikhaliyev

et al. 2024

J Comput Chem

Self Cite

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show abstract

Computational predictions on Brønsted acidic ionic liquid-catalyzed carbon dioxide conversion to five-membered heterocyclic carbonyl derivatives

Abstract: Experimentally conducted reactions between CO2 and various substrates (i.e., ethylenediamine (EDA), ethanolamine (ETA), ethylene glycol (EG), mercaptoethanol (ME), and ethylene dithiol (EDT)) are considered in a computational study. The reactions...

Cited by 1 publication

References 54 publications

Computational exploration of the copper(I)‐catalyzed conversion of hydrazones to dihalogenated vinyldiazene derivatives

Computational exploration of the copper(I)‐catalyzed conversion of hydrazones to dihalogenated vinyldiazene derivatives

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