Experimental and computational studies on the mechanism of zwitterionic ring-opening polymerization of δ-valerolactone with N-heterocyclic carbenes

Journal of Physical Chemistry B

Volumn 118, Issue 24, 2014, Pages 6553-6560

  Acharya, Ashwin K ^a   Chang, Young A ^c   Jones, Gavin O ^b   Rice, Julia E ^b   Hedrick, James L ^b   Horn, Hans W ^b   Waymouth, Robert M ^c  

^a UNIVERSITY OF CHICAGO   (United States)

^b IBM ALMADEN RESEARCH CENTER   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; ORGANIC COMPOUNDS;

ACTIVATION BARRIERS; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; N-HETEROCYCLIC CARBENES; NUCLEOPHILIC ATTACK; POLYVALEROLACTONE; RATE OF POLYMERIZATION; TETRAHEDRAL INTERMEDIATES;

POLYMERIZATION;

EID: 84962343787     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp500200b     Document Type: Article

References (46)

1. Semlyen, J. A. Cyclic Polymers; Kluwer Academic Publishers: Dordrecht, The Netherlands; Boston, MA, 2000.
2. Hoskins, J. N.; Grayson, S. M. Cyclic Polyesters: Synthetic Approaches and Potential Applications Polym. Chem. 2011, 2, 289-299
3. Tezuka, Y. Topological Polymer Chemistry: Progress of Cyclic Polymers in Syntheses, Properties, and Functions; 2012.
4. Kricheldorf, H. R. Cyclic Polymers: Synthetic Strategies and Physical Properties J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 251-284
5. Johnston, D. S. Macrozwitterion Polymerization. In Advances in Polymer Science; Springer: Berlin, Heidelberg, 1982; Vol. 42, pp 51-106.
6. Suzuki, M. Zwitterionic Polymerization. In Encyclopedia of Polymer Science and Technology; John Wiley & Sons, Inc.: 2002.
7. Brown, H. A.; Waymouth, R. M. Zwitterionic Ring-Opening Polymerization for the Synthesis of High Molecular Weight Cyclic Polymers Acc. Chem. Res. 2013, 46, 2585-2596
8. Brown, H. A.; Chang, Y. A.; Waymouth, R. M. Zwitterionic Polymerization to Generate High Molecular Weight Cyclic Poly(Carbosiloxane)s J. Am. Chem. Soc. 2013, 135, 18738-18741
9. Guo, L.; Lahasky, S. H.; Ghale, K.; Zhang, D. N-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Substituted N-Carboxyanhydrides toward Poly(α-Peptoid)s: Kinetic, Mechanism, and Architectural Control J. Am. Chem. Soc. 2012, 134, 9163-9171
10. Shin, E. J.; Brown, H. A.; Gonzalez, S.; Jeong, W.; Hedrick, J. L.; Waymouth, R. M. Zwitterionic Copolymerization: Synthesis of Cyclic Gradient Copolymers Angew. Chem., Int. Ed. 2011, 50, 6388-6391
11. Shin, E. J.; Jeong, W.; Brown, H. A.; Koo, B. J.; Hedrick, J. L.; Waymouth, R. M. Crystallization of Cyclic Polymers: Synthesis and Crystallization Behavior of High Molecular Weight Cyclic Poly(ε- Caprolactone)s Macromolecules 2011, 44, 2773-2779
12. Jeong, W.; Shin, E. J.; Culkin, D. A.; Hedrick, J. L.; Waymouth, R. M. Zwitterionic Polymerization: A Kinetic Strategy for the Controlled Synthesis of Cyclic Polylactide J. Am. Chem. Soc. 2009, 131, 4884-4891
13. Culkin, D. A.; Jeong, W.; Csihony, S.; Gomez, E. D.; Balsara, N. P.; Hedrick, J. L.; Waymouth, R. M. Zwitterionic Polymerization of Lactide to Cyclic Poly(Lactide) by Using N-Heterocyclic Carbene Organocatalysts Angew. Chem., Int. Ed. 2007, 46, 2627-2630
14. Brown, H. A.; De Crisci, A. G.; Hedrick, J. L.; Waymouth, R. M. Amidine-Mediated Zwitterionic Polymerization of Lactide ACS Macro Lett. 2012, 1, 1113-1115
15. Piedra-Arroni, E.; Ladavière, C.; Amgoune, A.; Bourissou, D. Ring-Opening Polymerization with Zn(C6F5)2-Based Lewis Pairs: Original and Efficient Approach to Cyclic Polyesters J. Am. Chem. Soc. 2013, 135, 13306-13309
16. Larionov, E.; Mahesh, M.; Spivey, A. C.; Wei, Y.; Zipse, H. Theoretical Prediction of Selectivity in Kinetic Resolution of Secondary Alcohols Catalyzed by Chiral DMAP Derivatives J. Am. Chem. Soc. 2012, 134, 9390-9399
17. Larionov, E.; Zipse, H. Organocatalysis: Acylation Catalysts Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1, 601-619
18. Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Çelebi- Ölçüm, N.; Houk, K. N. Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities Chem. Rev. 2011, 111, 5042-5137
19. Lai, C.-L.; Lee, H. M.; Hu, C.-H. Theoretical Study on the Mechanism of N-Heterocyclic Carbene Catalyzed Transesterification Reactions Tetrahedron Lett. 2005, 46, 6265-6270
20. Bonduelle, C.; Martín-Vaca, B.; Cossío, F. P.; Bourissou, D. Monomer versus Alcohol Activation in the 4-Dimethylaminopyridine-Catalyzed Ring-Opening Polymerization of Lactide and Lactic O-Carboxylic Anhydride Chem.-Eur. J. 2008, 14, 5304-5312
21. Alemán, C.; Betran, O.; Casanovas, J.; Houk, K. N.; Hall, H. K. Thermodynamic Control of the Polymerizability of Five-, Six-, and Seven-Membered Lactones J. Org. Chem. 2009, 74, 6237-6244
22. Kozuch, S.; Shaik, S. How to Conceptualize Catalytic Cycles? The Energetic Span Model Acc. Chem. Res. 2011, 44, 101-110
23. Xu, S.; Held, I.; Kempf, B.; Mayr, H.; Steglich, W.; Zipse, H. The DMAP-Catalyzed Acetylation of Alcohols-A Mechanistic Study (DMAP=4- (Dimethylamino)pyridine) Chem.-Eur. J. 2005, 11, 4751-4757
24. Lutz, V.; Glatthaar, J.; Würtele, C.; Serafin, M.; Hausmann, H.; Schreiner, P. R. Structural Analyses of N-Acetylated 4-(Dimethylamino)pyridine (DMAP) Salts Chem.-Eur. J. 2009, 15, 8548-8557
25. Duda, A.; Kowalski, A. Thermodynamics and Kinetics of Ring-Opening Polymerization. In Handbook of Ring-Opening Polymerization; Dubois, P.; Coulembier, O.; Raquez, J.-M., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: 2009; pp 1-51.
26. Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. Electronic Stabilization of Nucleophilic Carbenes J. Am. Chem. Soc. 1992, 114, 5530-5534
27. Kuhn, N.; Kratz, T. Synthesis of Imidazol-2-Ylidenes by Reduction of Imidazole-2(3H)-Thiones Synthesis 1993, 1993, 561-562
28. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
29. Gordon, M.; Schmidt, M. Advances in Electronic Structure Theory: GAMESS a Decade Later. In Theory and Applications of Computational Chemistry: The First Forty Years; Dykstra, C.; Frenking, G.; Kim, K.; Scuseria, G., Eds.; Elsevier: 2005; pp 1167-1189.
30. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; GAMESS 2012 R2.
31. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104-154119
32. Becke, A. D. Density-functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
33. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
34. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-Dependent Electron Liquid Correlation Energies for Local Spin Density Calculations: A Critical Analysis Can. J. Phys. 1980, 58, 1200-1211
35. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
36. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72, 650-654
37. Woon, D. E.; Dunning, T. H. Gaussian Basis Sets for Use in Correlated Molecular Calculations. V. Core-valence Basis Sets for Boron through Neon J. Chem. Phys. 1995, 103, 4572-4585
38. Kendall, R. A.; Dunning, T. H.; Harrison, R. J. Electron Affinities of the First-row Atoms Revisited. Systematic Basis Sets and Wave Functions J. Chem. Phys. 1992, 96, 6796-6806
39. Barone, V.; Cossi, M. Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model J. Phys. Chem. A 1998, 102, 1995-2001
40. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Energies, Structures, and Electronic Properties of Molecules in Solution with the C-PCM Solvation Model J. Comput. Chem. 2003, 24, 669-681
41. Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic Interaction of a Solute with a Continuum. A Direct Utilization of AB Initio Molecular Potentials for the Prevision of Solvent Effects Chem. Phys. 1981, 55, 117-129
42. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Use of Solution-Phase Vibrational Frequencies in Continuum Models for the Free Energy of Solvation J. Phys. Chem. B 2011, 115, 14556-14562
43. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. Iridium-Catalyzed Borylation of Benzene with Diboron. Theoretical Elucidation of Catalytic Cycle Including Unusual Iridium(V) Intermediate J. Am. Chem. Soc. 2003, 125, 16114-16126
44. 2 Zr-Catalyzed Hydrosilylation of Ethylene. Reaction Mechanism Including New Σ-Bond Activation J. Am. Chem. Soc. 2004, 126, 3332-3348
45. Gonzalez, C.; Schlegel, H. B. Reaction Path Following in Mass-Weighted Internal Coordinates J. Phys. Chem. 1990, 94, 5523-5527
46. Singh, U. C.; Kollman, P. A. An Approach to Computing Electrostatic Charges for Molecules J. Comput. Chem. 1984, 5, 129-145