Origins of the solvent effect on the propagation kinetics of acrylic acid and methacrylic acid

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 9, 2013, Pages 2024-2034

  Degirmenci, Isa ^a   Ozaltin, Tugba Furuncuoglu ^b   Karahan, Ozlem ^b   Van Speybroeck, Veronique ^c   Waroquier, Michel ^c   Aviyente, Viktorya ^d  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b BOGAZICI UNIVERSITY   (Turkey)

^c GHENT UNIVERSITY   (Belgium)

^d NONE

Author keywords

acrylic acid; kinetics; methacrylic acid; propagation; solvent effect

Indexed keywords

ASCORBIC ACID; CARBOXYLIC ACIDS; COMPUTATIONAL CHEMISTRY; FREE RADICAL POLYMERIZATION; FREE RADICALS; MOLECULAR DYNAMICS; RATE CONSTANTS; SOLVENTS;

ACRYLIC ACIDS; EFFECT OF WATER; METHACRYLIC ACIDS; POLYMERIZATION KINETICS; PROPAGATION; PROPAGATION KINETICS; RATE ACCELERATION; RATE OF POLYMERIZATION; RELATIVE RATES; SOLVENT EFFECTS;

KINETICS;

EID: 84875419771     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26589     Document Type: Article

References (110)

1. Y. E. Kirsh, Water-Soluble Poly-N-Vinylamides: Synthesis and Physico-Chemical Properties; Wiley: Chichester, New York, 1998.
2. S. K. Tripathy, J. Kumar, H. S. Nalwa, Handbook of Polyelectrolytes and their Applications;. Applications of Polyelectrolytes and Theoretical Models; American Scientific: Stevenson Ranch, Calif., 2002; Vol. 3.
3. S. Beuermann, M. Buback, Prog. Polym. Sci. 2002, 27, 191-254.
4. O. F. Olaj, I. Bitai, F. Hinkelmann, Macromol. Chem. Phys. 1987, 188, 1689-1702.
5. S. Beuermann, Macromol. Rapid Commun. 2009, 30, 1066-1088.
6. S. Beuermann, D. Nelke, Macromol. Chem. Phys. 2003, 204, 460-470.
7. K. F. ODriscoll, M. L. Monteiro, B. Klumperman, J. Polym. Sci. Part A: Polym. Chem. 1997, 35, 515-520.
8. M. D. Zammit, T. P. Davis, G. D. Willett, K. F. ODriscoll, J. Polym. Sci. Part A: Polym. Chem. 1997, 35, 2311-2321.
9. S. Harrisson, Barner-C. Kowollik, T. P. Davis, R. Evans, E. Rizzardo, M. Stenzel, M. Yin, Z. Phys. Chem. 2005, 219, 267-281.
10. H. Fischer, L. Radom, Angew. Chem. Int. Ed. Engl. 2001, 40, 1340-1371.
11. S. Beuermann, M. Buback, G. T. Russell, Macromol. Rapid Commun. 1994, 15, 647-653.
12. S. Beuermann, D. A. Paquet, J. H. McMinn, R. A. Hutchinson, Macromolecules 1997, 30, 194-197.
13. T. P. Davis, K. F. Odriscoll, M. C. Piton, M. A. Winnik, Macromolecules 1989, 22, 2785-2788.
14. R. A. Hutchinson, J. R. Richards, M. T. Aronson, Macromolecules 1994, 27, 4530-4537.
15. F. D. Kuchta, van A. M. Herk, A. L. German, Macromolecules 2000, 33, 3641-3649.
16. R. A. Lyons, J. Hutovic, M. C. Piton, D. I. Christie, P. A. Clay, B. G. Manders, S. H. Kable, R. G. Gilbert, Macromolecules 1996, 29, 1918-1927.
17. B. R. Morrison, M. C. Piton, M. A. Winnik, R. G. Gilbert, D. H. Napper, Macromolecules 1993, 26, 4368-4372.
18. F. Ganachaud, R. Balic, M. J. Monteiro, R. G. Gilbert, Macromolecules 2000, 33, 8589-8596.
19. H. R. Lin, Eur. Polym. J. 2001, 37, 1507-1510.
20. P. Pascal, M. A. Winnik, D. H. Napper, R. G. Gilbert, Macromolecules 1993, 26, 4572-4576.
21. S. A. Seabrook, M. P. Tonge, R. G. Gilbert, J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 1357-1368.
22. S. Beuermann, M. Buback, P. Hesse, F. D. Kuchta, I. Lacik, Van A. M. Herk, Pure Appl. Chem. 2007, 79, 1463-1469.
23. S. Beuermann, M. Buback, P. Hesse, S. Kukuckova, I. Lacik, Macromol. Symp. 2007, 248, 23-32.
24. S. Beuermann, M. Buback, P. Hesse, S. Kukuckova, I. Lacik, Macromol. Symp. 2007, 248, 41-49.
25. S. Beuermann, M. Buback, P. Hesse, I. Lacik, Macromolecules 2006, 39, 184-193.
26. I. Lacík, S. Beuermann, M. Buback, Macromolecules 2001, 34, 6224-6228.
27. I. Lacík, S. Beuermann, M. Buback, Macromolecules 2003, 36, 9355-9363.
28. I. Lacík, S. Beuermann, M. Buback, Macromol. Chem. Phys. 2004, 205, 1080-1087.
29. A. Chapiro, Pure Appl. Chem. 1981, 53, 643-655.
30. A. Chapiro, J. Dulieu, Eur. Polym. J. 1977, 13, 563-577.
31. V. F. Gromov, N. I. Galperina, T. O. Osmanov, P. M. Khomikovskii, A. D. Abkin, Eur. Polym. J. 1980, 16, 529-535.
32. K. Plochocka, J. Macromol. Sci. Rev. Macromol. Chem. Phys. 1981, C20, 67-148.
33. M. Buback, P. Hesse, R. A. Hutchinson, P. Kasak, I. Lacik, M. Stach, I. Utz, Ind. Eng. Chem. Res. 2008, 47, 8197-8204.
34. M. Stach, I. Lacik, D. Chorvat, M. Buback, P. Hesse, R. A. Hutchinson, L. Tang, Macromolecules 2008, 41, 5174-5185.
35. M. Buback, Macromol. Symp. 2009, 275-276, 90-101.
36. M. Dossi, G. Storti, D. Moscatelli, Macromol. Theory Simul. 2010, 19, 170-178.
37. T. Furuncuoglu, I. Ugur, I. Degirmenci, V. Aviyente, Macromolecules 2010, 43, 1823-1835.
38. Gomez-R. Balderas, M. L. Coote, D. J. Henry, H. Fischer, L. Radom, J. Phys. Chem A 2003, 107, 6082-6090.
39. Gomez-R. Balderas, M. L. Coote, D. J. Henry, L. Radom, J. Phys. Chem. A 2004, 108, 2874-2883.
40. D. J. Henry, M. L. Coote, Gomez-R. Balderas, L. Radom, J. Am. Chem. Soc. 2004, 126, 1732-1740.
41. J. P. A. Heuts, R. G. Gilbert, I. A. Maxwell, Macromolecules 1997, 30, 726-736.
42. J. P. A. Heuts, R. G. Gilbert, L. Radom, Macromolecules 1995, 28, 8771-8781.
43. J. P. A. Heuts, R. G. Gilbert, L. Radom, J. Phys. Chem. 1996, 100, 18997-19006.
44. D. M. Huang, M. J. Monteiro, R. G. Gilbert, Macromolecules 1998, 31, 5175-5187.
45. E. I. Izgorodina, M. L. Coote, Chem. Phys. 2006, 324, 96-110.
46. C. Y. Lin, E. I. Izgorodina, M. L. Coote, Macromolecules 2010, 43, 553-560.
47. D. Moscatelli, M. Dossi, C. Cavallotti, G. Storti, Macromol. Symp. 2007, 259, 337-347.
48. D. Moscatelli, M. Dossi, C. Cavallotti, G. Storti, J. Phys Chem. A 2011, 115, 52-62.
49. K. Van Cauter, K. Hemelsoet, V. Van Speybroeck, M. F. Reyniers, M. Waroquier, Int. J. Quantum Chem. 2005, 102, 454-460.
50. K. Van Cauter, V. Van Speybroeck, P. Vansteenkiste, M. F. Reyniers, M. Waroquier, Chemphyschem 2006, 7, 131-140.
51. Van K. Cauter, Van V. Speybroeck, M. Waroquier, Chemphyschem 2007, 8, 541-552.
52. M. W. Wong, L. Radom, J. Phys. Chem. 1995, 99, 8582-8588.
53. M. W. Wong, L. Radom, J. Phys Chem. A 1998, 102, 2237-2245.
54. I. Degirmenci, D. Avci, V. Aviyente, K. Van Cauter, V. Van Speybroeck, M. Waroquier, Macromolecules 2007, 40, 9590-9602.
55. I. Degirmenci, V. Aviyente, V. Van Speybroeck, M. Waroquier, Macromolecules 2009, 42, 3033-3041.
56. I. Degirmenci, S. Eren, V. Aviyente, B. De Sterck, K. Hemelsoet, V. Van Speybroeck, M. Waroquier, Macromolecules 2010, 43, 5602-5610.
57. M. Dossi, K. Liang, R. A. Hutchinson, D. Moscatelli, J. Phys. Chem. B 2010, 114, 4213-4222.
58. M. Dossi, G. Storti, D. Moscatelli, Polymer Reaction Engineering-10th International Workshop; Hamburg, Germany; 2011, 302, 16-25.
59. H. Gunaydin, S. Salman, N. S. Tuzun, D. Avci, V. Aviyente, Int. J. Quantum Chem. 2005, 103, 176-189.
60. K. Liang, M. Dossi, D. Moscatelli, R. A. Hutchinson, Macromolecules 2009, 42, 7736-7744.
61. D. Moscatelli, C. Cavallotti, M. Morbidelli, Macromolecules 2006, 39, 9641-9653.
62. T. F. Ozaltin, I. Degirmenci, V. Aviyente, C. Atilgan, B. De Sterck, V. Van Speybroeck, M. Waroquier, Polymer 2011, 52, 5503-5512.
63. S. Salman, A. Z. Albayrak, D. Avci, V. Aviyente, J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 2574-2583.
64. X. R. Yu, J. Pfaendtner, L. J. Broadbelt, J. Phys Chem. A 2008, 112, 6772-6782.
65. S. C. Thickett, R. G. Gilbert, Polymer 2004, 45, 6993-6999.
66. B. De Sterck, R. Vaneerdeweg, F. Du Prez, M. Waroquier, V. Van Speybroeck, Macromolecules 2010, 43, 827-836.
67. X. R. Yu, S. E. Levine, L. J. Broadbelt, Macromolecules 2008, 41, 8242-8251.
68. D. M. Smith, R. G. Lehmann, R. Narayan, G. E. Kozerski, J. R. Miller, Compost Sci. Utilization 1998, 6, 6-12.
69. P. Deglmann, I. Muller, F. Becker, A. Schafer, K. D. Hungenberg, H. Weiss, Macromol. React. Eng. 2009, 3, 496-515.
70. M. L. Coote, Macromol. Theory Simul. 2009, 18, 388-400.
71. D. J. Henry, M. B. Sullivan, L. Radom, J. Chem. Phys. 2003, 118, 4849-4860.
72. A. Klamt, COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design; Elsevier: Amsterdam, Oxford, 2005; p xi, 34 p.
73. A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235.
74. A. Klamt, V. Jonas, T. Burger, J. C. W. Lohrenz, J. Phys Chem. A 1998, 102, 5074-5085.
75. S. C. L. Kamerlin, M. Haranczyk, A. Warshel, Chemphyschem 2009, 10, 1125-1134.
76. M. J. Pilling, P. W. Seakins, Reaction Kinetics; Oxford University Press: Oxford, 1995; p xiii, 305p.
77. M. L. Coote, T. P. Davis, L. Radom, Macromolecules 1999, 32, 5270-5276.
78. M. L. Coote, T. P. Davis, L. Radom, Macromolecules 1999, 32, 2935-2940.
79. M. J. T. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, Al-M. A. Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and, J. A. Pople,; Gaussian 03. Revision D.01; Gaussian. Inc.: Wallingford CT, 2004.
80. D. M. Smith, A. Nicolaides, B. T. Golding, L. Radom, J. Am. Chem. Soc. 1998, 120, 10223-10233.
81. J. N. P. Louwen, C. E. V. Lenthe, ADF2008.01 COSMO-RS, SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands, 2008.
82. Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2004, 108, 6908-6918.
83. Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Theory Comput. 2006, 2, 364-382.
84. Y. Zhao, D. G. Truhlar, Theoret. Chem. Acc. 2008, 120, 215-241.
85. G. Black, J. M. Simmie, J. Comput. Chem. 2010, 31, 1236-1248.
86. A. Galano, Phys. Chem. Chem. Phys. 2011, 13, 7147-7157.
87. A. Galano, J. R. Alvarez-Idaboy, Org. Lett. 2009, 11, 5114-5117.
88. A. Galano, N. A. Macias-Ruvalcaba, O. N. M. Campos, J. Pedraza-Chaverri, J. Phys. Chem. B 2010, 114, 6625-6635.
89. T. T. Gao, J. M. Andino, J. R. Alvarez-Idaboy, Phys. Chem. Chem. Phys. 2010, 12, 9830-9838.
90. C. Iuga, J. R. Alvarez-Idaboy, A. Vivier-Bunge, J. Phys Chem. A 2011, 115, 5138-5146.
91. Leon-J. R. Carmona, A. Galano, J. Phys. Chem. B 2011, 115, 4538-4546.
92. A. Perez-Gonzalez, A. Galano, J. Phys. Chem. B 2011, 115, 1306-1314.
93. A. Vega-Rodriguez, J. R. Alvarez-Idaboy, Phys. Chem. Chem. Phys. 2009, 11, 7649-7658.
94. E. Velez, J. Quijano, R. Notario, E. Pabon, J. Murillo, J. Leal, E. Zapata, G. Alarcon, J. Phys. Org. Chem. 2009, 22, 971-977.
95. C. Zavala-Oseguera, J. R. Alvarez-Idaboy, G. Merino, A. Galano, J. Phys Chem. A 2009, 113, 13913-13920.
96. Y. Zhao, D. G. Truhlar, J. Chem. Theory Comput. 2007, 3, 289-300.
97. D. A. McQuarrie, J. D. Simon, Physical Chemistry: A Molecular Approach; University Science Books: Sausalito, Calif., 1997; p xxiii, 1270p.
98. P. W. Atkins, De J. Paula, Atkins' Physical Chemistry, 8th ed.; Oxford University Press: Oxford, New York, 2006; p xxx, 1064 p.
99. E. Cances, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041.
100. B. Mennucci, E. Cances, J. Tomasi, J. Phys. Chem. B 1997, 101, 10506-10517.
101. B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 106, 5151-5158.
102. J. Tomasi, B. Mennucci, E. Cances, J. Mol. Struct. (Theochem) 1999, 464, 211-226.
103. B. De Sterck, V. Van Speybroeck, S. Mangelinckx, G. Verniest, N. De Kimpe, M. Waroquier, J. Phys Chem. A 2009, 113, 6375-6380.
104. C. P. Kelly, C. J. Cramer, D. G. Truhlar, J. Chem. Theory Comput. 2005, 1, 1133-1152.
105. C. P. Kelly, C. J. Cramer, D. G. Truhlar, J. Phys Chem. A 2006, 110, 2493-2499.
106. Van V. Speybroeck, K. Moonen, K. Hemelsoet, C. V. Stevens, M. Waroquier, J. Am. Chem. Soc. 2006, 128, 8468-8478.
107. M. D. Liptak, K. C. Gross, P. G. Seybold, S. Feldgus, G. C. Shields, J. Am. Chem. Soc. 2002, 124, 6421-6427.
108. D. N. Theodorou, U. W. Suter, Macromolecules 1985, 18, 1467-1478.
109. H. Sun, J. Phys. Chem. B 1998, 102, 7338-7364.
110. H. C. Andersen, J. Chem. Phys. 1980, 72, 2384-2393.