A Strained Ion Pair Permits Carbon Dioxide Fixation at Atmospheric Pressure by C-H H-Bonding Organocatalysis was written by Xu, Jiaxi;Xian, Anmei;Li, Zhenjiang;Liu, Jingjing;Zhang, Zhihao;Yan, Rui;Gao, Luoyu;Liu, Bo;Zhao, Lili;Guo, Kai. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C4H12ClN The following contents are mentioned in the article:
The cycloadditions of carbon dioxide into epoxides to afford cyclic carbonates by H-bond donor (HBD) and onium halide (X) cocatalysis have emerged as a key strategy for CO2 fixation. However, if the HBD is also a halide receptor, the two will quench each other, decreasing the catalytic activity. Here, we propose a strained ion pair tris(alkylamino)cyclopropenium halide (TAC·X), in which TAC repels X. TAC possesses a pos. charged cyclopropenium core that makes the vicinal C-H or N-H a nonclassical HBD. The interionic strain within TAC·X makes TAC a more electrophilic HBD, allowing it to activate the oxygen of the epoxide and making X more nucleophilic and better able to attack the methylene carbon of the epoxide. NMR titration spectra and computational studies were employed to probe the mechanism of the cycloaddition of CO2 to epoxides reactions under the catalysis of TAC·X. The 1H and 13C{1H}NMR titration spectra of the catalyst with the epoxide substrate unambiguously confirmed H-bonding between TAC and the epoxide. DFT computational studies identified the transition states in the ring-opening of the epoxide (TS1) and in the ring-closure of the cyclic carbonate (TS2). This study involved multiple reactions and reactants, such as Tetramethylammonium chloride (cas: 75-57-0Synthetic Route of C4H12ClN).
Tetramethylammonium chloride (cas: 75-57-0) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Synthetic Route of C4H12ClN
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics