Connecting Gas-Phase Computational Chemistry to Condensed Phase Kinetic Modeling: The State-of-the-Art

Overview

Journal Polymers (Basel)

Publisher MDPI

Date 2021 Sep 28

PMID 34577928

Citations 5

Authors

Mariya Edeleva

Paul H M Van Steenberge

Maarten K Sabbe

Dagmar R Dhooge

Affiliations

Soon will be listed here.

Abstract

In recent decades, quantum chemical calculations (QCC) have increased in accuracy, not only providing the ranking of chemical reactivities and energy barriers (e.g., for optimal selectivities) but also delivering more reliable equilibrium and (intrinsic/chemical) rate coefficients. This increased reliability of kinetic parameters is relevant to support the predictive character of kinetic modeling studies that are addressing actual concentration changes during chemical processes, taking into account competitive reactions and mixing heterogeneities. In the present contribution, guidelines are formulated on how to bridge the fields of computational chemistry and chemical kinetics. It is explained how condensed phase systems can be described based on conventional gas phase computational chemistry calculations. Case studies are included on polymerization kinetics, considering free and controlled radical polymerization, ionic polymerization, and polymer degradation. It is also illustrated how QCC can be directly linked to material properties.

Citing Articles

Improved Approach for ab Initio Calculations of Rate Coefficients for Secondary Reactions in Acrylate Free-Radical Polymerization.

Lugo F, Edeleva M, Van Steenberge P, Sabbe M Polymers (Basel). 2024; 16(7).

PMID: 38611129 PMC: 11013146. DOI: 10.3390/polym16070872.

Machine learning from quantum chemistry to predict experimental solvent effects on reaction rates.

Chung Y, Green W Chem Sci. 2024; 15(7):2410-2424.

PMID: 38362410 PMC: 10866337. DOI: 10.1039/d3sc05353a.

Free-Radical Propagation Rate Coefficients of Diethyl Itaconate and Di-n-Propyl Itaconate Obtained via PLP-SEC.

Meyer E, Weege T, Vana P Polymers (Basel). 2023; 15(6).

PMID: 36987126 PMC: 10056010. DOI: 10.3390/polym15061345.

Molecular Pathways for Polymer Degradation during Conventional Processing, Additive Manufacturing, and Mechanical Recycling.

Ceretti D, Edeleva M, Cardon L, Dhooge D Molecules. 2023; 28(5).

PMID: 36903589 PMC: 10004996. DOI: 10.3390/molecules28052344.

Determination of Reactivity Ratios from Binary Copolymerization Using the k-Nearest Neighbor Non-Parametric Regression.

Fazakas-Anca I, Modrea A, Vlase S Polymers (Basel). 2021; 13(21).

PMID: 34771367 PMC: 8588380. DOI: 10.3390/polym13213811.

References

Sterling C, Bjornsson R . Multistep Explicit Solvation Protocol for Calculation of Redox Potentials. J Chem Theory Comput. 2018; 15(1):52-67. DOI: 10.1021/acs.jctc.8b00982. View

Kroger L, Kopp W, Leonhard K . Prediction of Chain Propagation Rate Constants of Polymerization Reactions in Aqueous NIPAM/BIS and VCL/BIS Systems. J Phys Chem B. 2017; 121(13):2887-2895. DOI: 10.1021/acs.jpcb.6b09147. View

Rosen B, Percec V . Single-electron transfer and single-electron transfer degenerative chain transfer living radical polymerization. Chem Rev. 2009; 109(11):5069-119. DOI: 10.1021/cr900024j. View

Kraka E, Cremer D . Characterization of CF bonds with multiple-bond character: bond lengths, stretching force constants, and bond dissociation energies. Chemphyschem. 2009; 10(4):686-98. DOI: 10.1002/cphc.200800699. View

Hodgson J, Roskop L, Gordon M, Lin C, Coote M . Side reactions of nitroxide-mediated polymerization: N-O versus O-C cleavage of alkoxyamines. J Phys Chem A. 2010; 114(38):10458-66. DOI: 10.1021/jp1064165. View

Dong F, Wagoner J, Baker N . Assessing the performance of implicit solvation models at a nucleic acid surface. Phys Chem Chem Phys. 2008; 10(32):4889-902. PMC: 2538626. DOI: 10.1039/b807384h. View

Moors S, Brigou B, Hertsen D, Pinter B, Geerlings P, Van Speybroeck V . Influence of Solvation and Dynamics on the Mechanism and Kinetics of Nucleophilic Aromatic Substitution Reactions in Liquid Ammonia. J Org Chem. 2016; 81(4):1635-44. DOI: 10.1021/acs.joc.5b02794. View

Sabbe M, Vandeputte A, Reyniers M, Van Speybroeck V, Waroquier M, Marin G . Ab initio thermochemistry and kinetics for carbon-centered radical addition and beta-scission reactions. J Phys Chem A. 2007; 111(34):8416-28. DOI: 10.1021/jp072897t. View

Vlachy V . Ionic effects beyond Poisson-Boltzmann theory. Annu Rev Phys Chem. 2004; 50:145-65. DOI: 10.1146/annurev.physchem.50.1.145. View

10.

Raju M, Ganesh P, Kent P, van Duin A . Reactive Force Field Study of Li/C Systems for Electrical Energy Storage. J Chem Theory Comput. 2015; 11(5):2156-66. DOI: 10.1021/ct501027v. View

11.

Rodriguez-Sanchez I, Glossman-Mitnik D, Zaragoza-Contreras E . Theoretical evaluation of the order of reactivity of transfer agents utilized in RAFT polymerization: group Z. J Mol Model. 2009; 15(9):1133-43. DOI: 10.1007/s00894-009-0476-3. View

12.

Li L, Liu J, Hu J, Wania F . Degradation of Fluorotelomer-Based Polymers Contributes to the Global Occurrence of Fluorotelomer Alcohol and Perfluoroalkyl Carboxylates: A Combined Dynamic Substance Flow and Environmental Fate Modeling Analysis. Environ Sci Technol. 2017; 51(8):4461-4470. DOI: 10.1021/acs.est.6b04021. View

13.

Tanaka A, Nakashima K . DFT studies of ESR parameters for N-O centered radicals, N-alkoxyaminyl and aminoxyl radicals. Magn Reson Chem. 2011; 49(9):603-10. DOI: 10.1002/mrc.2792. View

14.

Derboven P, Van Steenberge P, Vandenbergh J, Reyniers M, Junkers T, Dhooge D . Improved Livingness and Control over Branching in RAFT Polymerization of Acrylates: Could Microflow Synthesis Make the Difference?. Macromol Rapid Commun. 2015; 36(24):2149-55. DOI: 10.1002/marc.201500357. View

15.

Allam O, Cho B, Kim K, Jang S . Application of DFT-based machine learning for developing molecular electrode materials in Li-ion batteries. RSC Adv. 2022; 8(69):39414-39420. PMC: 9090775. DOI: 10.1039/c8ra07112h. View

16.

Coote M, Pross A, Radom L . Variable trends in R-X bond dissociation energies (R = Me, Et, i-Pr, t-Bu). Org Lett. 2003; 5(24):4689-92. DOI: 10.1021/ol035860+. View

17.

MacKerell Jr A, Feig M, Brooks 3rd C . Extending the treatment of backbone energetics in protein force fields: limitations of gas-phase quantum mechanics in reproducing protein conformational distributions in molecular dynamics simulations. J Comput Chem. 2004; 25(11):1400-15. DOI: 10.1002/jcc.20065. View

18.

Pezeshki S, Lin H . Molecular dynamics simulations of ion solvation by flexible-boundary QM/MM: on-the-fly partial charge transfer between QM and MM subsystems. J Comput Chem. 2014; 35(24):1778-88. DOI: 10.1002/jcc.23685. View

19.

Pai S, Yeo B, Han S . Development of the ReaxFFCBN reactive force field for the improved design of liquid CBN hydrogen storage materials. Phys Chem Chem Phys. 2015; 18(3):1818-27. DOI: 10.1039/c5cp05486a. View

20.

Izgorodina E, Coote M . Reliable low-cost theoretical procedures for studying addition-fragmentation in RAFT polymerization. J Phys Chem A. 2006; 110(7):2486-92. DOI: 10.1021/jp055158q. View