First principles prediction of the propagation rate coefficients of acrylic and vinyl esters: Are we there yet?

Macromolecules

Volumn 43, Issue 1, 2010, Pages 553-560

  Lin, Ching Yeh ^a   Izgorodina, Ekaterina I ^a,b   Coote, Michelle L ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLICS; CONFORMATIONS; CONTINUUM MECHANICS; ESTERS; FREE ENERGY; GASES; HOMOPOLYMERIZATION; HYDROGEN BONDS; MOLECULAR ORBITALS; SOLVATION;

AB INITIO MOLECULAR ORBITAL THEORY; ARRHENIUS PARAMETERS; CONFORMATIONAL ANALYSIS; CONTINUUM MODEL; CORRESPONDING SOLUTIONS; COSMO-RS; DFT METHOD; DIMER MODEL; EXPERIMENTAL DATA; FIRST-PRINCIPLES; GASPHASE; HINDERED ROTORS; LARGE DEVIATIONS; METHYL ACRYLATES; ORDERS OF MAGNITUDE; PROPAGATION RATE COEFFICIENT; PROPAGATION STEP; QUALITATIVE DIFFERENCES; RATE COEFFICIENTS; SOLUTION PHASE; SOLVATION ENERGY; STABILIZING EFFECTS; THERMODYNAMIC CYCLE; TRANSITION STATE; TRANSITION STRUCTURES; VINYL ACETATES; VINYL ESTERS;

POLYVINYL ACETATES;

EID: 84962429313     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma902049g     Document Type: Article

References (78)

1. (a) Coote, M. L.; Zammit, M. D.; Davis, T. P. Trends Polym. Sci. 1996, 4, 189-196.
2. (b) van Herk, A. M. Macromol. Theory Simul 2000, 9, 433-441.
3. (c) Beuermann, S.; Buback, M. Prog. Polym. Sci. 2002,27,191-254.
4. (d) Barner-Kowollik, C.; Buback, M.; Egorov, M.; Fukuda, T.; Goto, A.; Olaj, O. R; Russell, G. T.; Vana, P.; Yamada, B.; Zetterlund, P. B. Prog. Polym. Sci. 2005, 30, 605-643.
5. For a discussion of this problem, see for example: Barner-Kowollik, C.; Coote, M. L.; Davis, T. P.; Radom, L.; Vana, P. J. Polym. Sci. A Polym. Chem. 2003,41,2828-2832.
6. For recent reviews of applications in free-radical polymerization, see for example: (a) Coote, M. L. Macromol. Theory Simul. 2009, 18, 388-400.
7. (b) Coote, M. L.; Krenske, E. H.; Izgorodina, E. I. Macromol. Rapid Commun. 2006, 27,473-497.
8. Izgorodina, E. L; Coote, M. L. Chem. Phys. 2006, 324, 96-110.
9. Coote, M. L.; Izgorodina, E. I.; Krenske, E. H.; Busch, M.; Barner-Kowollik, C. Macromol. Rapid Commun. 2006, 27, 1015-1022.
10. McLeary, J. B.; Calitz, F. M.; McKenzie, J. M.; Tonge, M. P.; Sanderson, R. D.; Klumperman, B. Macromolecules 2004, 37, 2383-2394.
11. (a) Klamt, A.; Schueuermann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805.
12. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
13. Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117-129.
14. Tomasi, J. Theor. Chem. Acc. 2004, 112, 184-203.
15. Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70-77.
16. See for example: Ho, J.; Coote, M. L. J. Chem. Theory Comput. 2009, 5, 295-306.
17. (a) Lin, C. Y.; Coote, M. L.; Gennaro, A.; Matyjaszewski, K. J. Am. Chem. Soc. 2008, 130, 12762-12774.
18. (b) Tang, W; Kwak, Y.; Braunecker, W; Tsarevsky, N. V; Coote, M. L.; Matyjaszewski, K. J. Am. Chem. Soc. 2008, 130, 10702-10713.
19. Lin, C. Y.; Coote, M. L. Aust. J. Chem. 2009, in press. DOI: 10.1071/ CH09269.
20. See for example: (a)Namazian, M.; Coote, M. L. J. Phys. Chem. A 2007, 111, 7227-7232.
21. (b) Hodgson, J. L.; Namazian, M.; Bottle, S. E.; Coote, M. L. J. Phys. Chem. A 2007, 111, 13595-13605.
22. (c) Namazian, M.; Zare, H. R.; Coote, M. L. Biophys. Chem. 2008, 132, 64-68.
23. (d) Namazian, M.; Siahrostami, S.; Coote, M. L. J. Fluorine Chem. 2008, 129, 222-225.
24. (e) Blinco, J. P.; Hodgson, J. L.; Morrow, B. J.; Walker, J. R.; Will, G. D.; Coote, M. L.; Bottle, S. E. J. Org. Chem. 2008, 73, 6763-6771.
25. (f) Zare, H.; Eslami, M.; Namazian, M.; Coote, M. L. J. Phys. Chem. B 2009,113, 8080-8085.
26. Beuermann, S.; Buback, M.; Hesse, P.; Kuchta, F.-D.; Lacik, I.; Van Herk, A. M. Pure Appl. Chem. 2007, 79 (8), 1463-1469.
27. Thickett, S. C.; Gilbert, R. G. Polymer 2004, 45, 6993-6999.
28. Morrison, D. A.; Davis, T. P. Macromol. Chem. Phys. 2000, 201, 2128-2137.
29. Degirmenci, I.; Avci, D.; Aviyente, V.; Van Cauter, K.; Van Speybroeck, V.; Waroquier, M. Macromolecules 2007, 40, 9590-9602.
30. (a) Klamt, A. J. Phys. Chem. 1995, 99, 2224-2235.
31. b) Klamt, A. COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design; Elsevier Science Ltd.: Amsterdam, The Netherlands, 2005.
32. (c) Klamt, A.; Jonas, V; Burger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074-5085.
33. Degirmenci, I.; Aviyente, V.; Van Speybroeck, V.; Waroquier, M. Macromolecules 2009, 42, 3033-3041.
34. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
35. Henry, D. J.; Sullivan, M. B.; Radom, L. J. Chem. Phys. 2003, 118, 4849-4860.
36. (a) Vreven, T.; Morokuma, K. J. Chem. Phys. 1999, 111, 8799 -8803.
37. (b) Vreven, T.; Morokuma, K. J. Comput. Chem. 2000, 21, 1419-1432.
38. See for example: (a) Izgorodina, E. I.; Coote, M. L. J. Phys. Chem. A 2006, 110, 2486-2492.
39. (b) Izgorodina, E. I.; Brittain, D. R. B.; Hodgson, J. L.; Krenske, E. H.; Lin, C. Y.; Namazian, M.; Coote, M. L. J. Phys. Chem. A 2007, 111, 10754-10768.
40. (c) Lin, C. Y.; Hodgson, J. L.; Namazian, M.; Coote, M. L. J. Phys. Chem. A 2009, 113, 3690-3697.
41. See for example: (a) Truhlar, D. G.; Garrett, B. C.; Klippenstein, S. J. J. Phys. Chem. 1996, 100, 12771-12800.
42. See for example: (a) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969.
43. (b) Robinson, P. J. J. Chem. Educ 1978, 55, 509-510.
44. (c) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics; Prentice Hall: Englewood Cliffs, NJ, 1989.
45. These formulae are outlined in full in the Supporting Information of an earlier publication in this journal: Coote, M. L.; Radom, L. Macromolecules 2004,37, 590-596.
46. Lin, C. Y.; Izgorodina, E. I.; Coote, M. L. J. Phys. Chem. A 2008, 112, 1956-1964.
47. Van Cauter, K.; Van Speybroeck, V.; Vansteenkiste, P.; Reyniers, M.-F.; Waroquier, M. ChemPhysChem 2006, 7, 131-140.
48. Liptak, M. D.; Gross, K. G.; Seybold, P. G.; Feldgus, S.; Shields, G. C. J. Am. Chem. Soc. 2002, 124, 6421-6421.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian, Inc.: Pittsburgh PA, 2003.
50. MOLPRO, version 2006.6, a package of ab initio programs. Werner, H.-J.; Knowles, P. J.; Lindh, R.; Manby, F. R.; Schütz, M.; Celani, P.; Korona, T.; Rauhut, G.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; Lloyd, A. W.; McNicholas, S. J.; Meyer, W.; Mura, M. E.; Nicklass, A.; Palmieri, P.; Pitzer, R.; Schumann, U.; Stoll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T. See: http://www.molpro.net.
51. Louwen, J. N.; Pye, C.; Lenthe, E. v. ADF2008.01 COSMO-RS, SCM, Theoretical Chemistry: Vrije Universiteit: Amsterdam, The Netherlands, http://www.scm.com, 2008.
52. Pye, C. C.; Ziegler, T.; van Lenthe, E.; Louwen, J. N. Can. J. Chem. 2009, 87, 790-797.
53. This program is freely available from http://rsc.anu.edu.au/-cylin/ scripts.html.
54. Manders, B. G. Ph.D. Thesis, Eindhoven University of Technology: Eindhoven, The Netherlands, 1997.
55. Hutchinson, R. A.; Paquet, D. A., Jr.; McMinn, J. H.; Beuermann, S.; Fuller, R. E.; Jackson, C. DCHEMA Monogr. 1995, 131,467-492.
56. Lobachevsky, S.; Schiesser, C. H.; Lin, C. Y.; Coote, M. L. J. Phys. Chem. A 2008, 112, 13622-13621.
57. See, for example: (a) Gómez-Balderas, R.; Coote, M. L.; Henry, D. J.; Radom, L. J. Phys. Chem. A 2004, 108, 2874-2883.
58. (b) Coote, M. L.; Wood, G. P. F.; Radom, L. J. Phys. Chem. A 2002, 106, 12124-12138.
59. Martin, J. M. L.; De Oliveira, G. J. J. Chem. Phys. 1999, 111, 1843-1856.
60. National Institute of Standards and Technology (NIST), Chemical Kinetics Database on the Web, Standard Reference Database 17, Version 7.0 (Web Version), Release 1.2 http://kinetics.nist.gov/index.php
61. Luo, Y.-R., Handbook of Bond Dissociation Energies in Organic Compounds. CRC Press: Boca Raton, FL, 2003.
62. See for example: Buback, M.; Müller, E. Macromol. Chem. Phys. 2007, 208, 581-593.
63. (a) Coote, M. L.; Radom, L. Macromolecules 2004, 37, 590-596.
64. (b) Coote, M. L.; Izgorodina, E. I.; Cavigliasso, G. E.; Roth, M.; Busch, M.; Barner-Kowollik, C. Macromolecules 2006, 39, 4585-4591.
65. -1 above the gauche addition structure; however, its increased vibrational energy results in an enthalpy at 298.15 K (and hence Arrhenius activation energy) that is slightly lower.
66. On the basis of a crude electrostatic model, the strength of hydrogen bond should beinversely related to the dielectric constant of the medium. The reality is of course more complex but it is nonetheless generally observed that the strength of hydrogen bonding interactions decreases significantly as the polarity of the reaction medium increases. For a discussion, see for example: Chen, J.; McAllister, M. A.; Lee, J. K.; Houk, K. N. J. Org. Chem. 1998, 63, 4611-4619.
67. See for example: (a) Choi, C. C.; Kertesz, M.; Karpfen, A. Chem. Phys. Lett. 1997, 276, 266-268.
68. (b) Curtiss, L. A.; Raghavachari, K.; Redfem, P. C.; Pople, J. A. J. Chem. Phys. 2000, 112, 7374-7383.
69. (c) Woodcock, H. L.; Schaefer, H. F., III; Schreiner, P. R. J. Phys. Chem. A 2002, 106, 11923-11931.
70. (d) Izgorodina, E. I.; Coote, M. L.; Radom, L. J. Phys. Chem. A 2005, 109, 7558-7566.
71. (e) Check, C. E.; Gilbert, T. M. J. Org. Chem. 2005, 70, 9828-9834.
72. (f) Grimme, S. Angew. Chem., Int. Ed. 2006, 45, 4460-4464.
73. (g) Schreiner, P. R.; Fokin, A. A.; Pascal, R. A., Jr.;deMeijere, A. Org. Lett. 2006, 8, 3635-3638.
74. (h) Wodrich, M. D.; Corminbœf, C.; von Ragué Schleyer, P. Org. Lett. 2006, 8, 3631-3634.
75. (i) Wodrich, M. D.; Corminbœf, C.; Schreiner, P. R.; Fokin, A. A.; von Ragué Schleyer, P. Org. Lett. 2007, 9, 1851-1854.
76. (j) Grimme, S.; Steinmetz, M.; Korth, M. J. Chem. Theory Comput. 2007, 5, 42-45.
77. (k) Schreiner, P. R. Angew. Chem., Int. Ed. 2007, 46, 4217-4219.
78. (l) Brittain, D. R. B.; Lin, C. Y.; Gilbert, A. T. B.; Izgorodina, E. I.; Gill, P. M. W; Coote, M. L. Phys. Chem. Chem. Phys. 2009, 11, 1138-1142.