DFT Study on the Molecular Mechanism, Thermodynamic and Kinetic Parameters of Cycloaddition Reaction of Aziridine with CO2 in the Presence of Organocatalysts (TBD and 7-Azaindole)
DOI:
https://doi.org/10.48048/tis.2023.6520Keywords:
Cycloaddition, Carbon dioxide, Aziridine, Trazabicyclodecene, 7-azaindole, TBD, Zwitterion, Coupling reactionAbstract
The catalytic conversions of CO2 into value added chemicals have attracted the interest of many visionary researchers. In this work, the coupling reaction of aziridine with CO2 has been investigated in the absence and presence of organocatalysts (TBD and 7-azaindole) computationally using density functional theory method. The kinetic and thermodynamic parameters of each mechanism were calculated at B3LYP/6-31G (d) level. The results show that, the TBD and 7-azaindole catalyzed reactions of aziridine with CO2 have significantly lower the energy barrier compared to a single step concerted non-catalyzed one. In TBD catalyzed reaction, mechanism I in which the TBD catalyst first interact with CO2 to form TBD-CO2 adduct (zwitterion) and then the zwitterion formed facilitated the ring opening of aziridine to form intermediate is the favorable path. In the case of 7-azaindole catalyzed reaction, mechanism 1 is the most favorable pathway in both gas phase and water phase. However, these parameters were significantly affected in the presence of water using Solvent Model Density (SMD).
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N Ahmad and L Du. Effects of energy production and CO2 emissions on economic growth in Iran: ARDL approach. Energy 2017; 123, 521-37.
S Sibilio, A Rosato, G Ciampi, M Scorpio and A Akisawa. Building-integrated trigeneration system: Energy, environmental and economic dynamic performance assessment for Italian residential applications. Renew. Sustain. Energ. Rev. 2017; 68, 920-33.
M Kahia, MSB Aïssa and C Lanouar. Renewable and non-renewable energy use-economic growth nexus: The case of MENA net oil importing countries. Renew. Sustain. Energ. Rev. 2017; 71, 127-40.
M Ahiduzzaman and AKMS Islam. Greenhouse gas emission and renewable energy sources for sustainable development in Bangladesh. Renew. Sustain. Energ. Rev. 2011; 15, 4659-66.
K Goto, K Yogo and T Higashii. A review of efficiency penalty in a coal-fired power plant with post-combustion CO2 capture. Appl. Energ. 2013; 111, 710-20.
WH Chen, SM Chen and CI Hung. Carbon dioxide capture by single droplet using Selexol, Rectisol and water as absorbents: A theoretical approach. Appl. Energ. 2013; 111, 731-41.
K Sołtys-Brzostek, M Terlecki, K Sokołowsi and J Lewiński. Chemical fixation and conversion of CO2 into cyclic and cage-type metal carbonates. Coord. Chem. Rev. 2017; 334, 199-231.
J Peng, Y Geng, HJ Yang, W He, Z Wei and J Yang. Efficient solvent-free fixation of CO2 into cyclic carbonates catalyzed by Bi (III) porphyrin/TBAI at atmospheric pressure. Mol. Catal. 2017; 432, 37-46.
Y Zhang, Y Zhang, Y Ren and O Ramström. Synthesis of chiral oxazolidinone derivatives through lipase-catalyzed kinetic resolution. J. Mol. Catal. B Enzym. 2015; 122, 29-34.
ZZ Yang, LN He, J Gao, AH Liu and B Yu. Carbon dioxide utilization with C-N bond formation: Carbon dioxide capture and subsequent conversion. Energ. Environ. Sci. 2012; 5, 6602-39.
S Kim, H Shi and JY Lee. CO2 absorption mechanism in amine solvents and enhancement of CO2 capture capability in blended amine solvent. Int. J. Greenhouse Gas Contr. 2016; 45, 181-8.
MF Rojas, FL Bernard, A Aquino, J Borges, FD Vecchia and S Menezes. Poly(ionic liquid)s as efficient catalyst in transformation of CO2 to cyclic carbonate. J. Mol. Catal. A Chem. 2014; 392, 83-8.
M Azzi and S White. 20 - emissions from amine-based post-combustion CO2 capture plants. Woodhead Publish. 2016; 2016, 487-504.
W Koch and MC Holthausen. A chemist's guide to density functional theory. 2nd ed. Wiely-VCH, Weinheim, Germany, 2000.
BO Milhøj, ED Hedegard and SPA Sauer. On the use of locally dense basis sets in the calculation of EPR hyperfine couplings: A study on model systems for bio-inorganic Fe and Co complexes. Curr. Inorg. Chem. 2013; 3, 270-83.
A Łapczuk-Krygier, VY Korotaev, AY Barkov, VY Sosnovskikh, E Jasińska and R Jasiński. A DFT computational study on the molecular mechanism of the nitro group migration in the product derived from 3-nitro-2 (trifluoromethyl)-2H-chromene and 2-(1-phenylpropylidene)malononitrile. J. Fluorine Chem. 2014; 168, 236-9.
AV Marenich, CJ Cramer and DG Truhlar. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. 2009; 113, 6378-96.
ELM Miguel, CIL Santos, CM Silva and JR Pliego. How accurate is the SMD model for predicting free energy barriers for nucleophilic substitution reactions in polar protic and dipolar aprotic solvents. J. Braz. Chem. Soc. 2016; 27, 2055-61.
LR Domingo, P Perez and JA Saez. Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions. RSC Adv. 2013; 3,1486-94.
LR Domingo. A new C-C bond formation model based on the quantum chemical topology of electron density. RSC Adv. 2014; 4, 32415-28.
AE Reed, LA Curtiss and F Weinhold. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988; 88, 899-926.
W Li, D Huang and Y Lv. Mechanism of N-heterocyclic carbene-catalyzed chemical fixation of CO2 with aziridines: A theoretical study. RSC Adv. 2014; 4, 17236-44.
A Axelsson, A Antoine-Michard and H Sunden. Organocatalytic valorisation of glycerol via a dual NHC-catalysed telescoped reaction. Green Chem. 2017; 19, 2477-81.
C Sabot, KA Kumar, S Meunier and C Mioskowski. A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions. Tetrahedron Lett. 2007; 48, 3863-6.
S Matsukawa, J Kimura and M Yoshioka. TBD or PS-TBD-catalyzed one-pot synthesis of cyanohydrin carbonates and cyanohydrin acetates from carbonyl compounds. Molecule 2016; 21, 1030.
JE Gómez and AW Kleij. Recent progress in stereoselective synthesis of cyclic organic carbonates and beyond. Curr. Opin. Green Sustain. 2017; 3, 55-60.
AA Chaugule, AH Tamboli and H Kim. Ionic liquid as a catalyst for utilization of carbon dioxide to production of linear and cyclic carbonate. Fuel 2017; 200, 316-32.
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