Why δ-valerolactone polymerizes and γ-butyrolactone does not

Journal of Organic Chemistry

Volumn 73, Issue 7, 2008, Pages 2674-2678

  Houk, K N ^a   Jabbari, Arash ^a   Hall Jr , H K ^b   Alemán, Carlos ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b University of Arizona   (United States)

^c UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; GAMMA RAYS; MATHEMATICAL MODELS; POLYMERIZATION; STRAIN ENERGY;

CYCLIC LACTONES; HOMOPOLYESTERS,;

POLYESTERS;

GAMMA BUTYROLACTONE; HYDROXYBUTYRIC ACID; LACTONE DERIVATIVE; POLYESTER;

ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; ENERGY; ENTHALPY; GEOMETRY; POLYMERIZATION; QUANTUM CHEMISTRY; RING OPENING;

EID: 84961983857     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702567v     Document Type: Article

References (66)

1. (a) Carothers, W. H. Chem. Rev. 1931, 8, 353.
2. (b) Hall, H. K., Jr.; Schneider, A. K. J. Am. Chem Soc. 1958, 80, 6409.
3. (c) Biela, T.; Kowalski, A.; Libiszowski, J.; Duda, A.; Penczek, S. Macromol. Symp. 2006, 240, 47
4. (d) Duda, A.; Kowalski, A.; Libiszowski, J.; Penczek, S. Macromol. Symp. 2005, 224, 71.
5. (e) Duda, A.; Libiszowski, J.; Mosnacek, J.; Penczek, S. Macromol. Symp. 2005, 226, 18.
6. (a) Coulembier, O; Degu, P.; Hendrick, J. L.; Dubois, P. Progr. Polymer Sci. 2006, 31 723.
7. (b) Albertssohn, A. C.; Varma, I. K. Biomacromolecules 2003, 4, 1466.
8. Korte, F.; Glet, W. J. Polym. Sci. Polym. Lett. Ed. 1966, 4, 685.
9. (a) Duda, A.; Penczek, S. Macromol. Chem. Phys. 1996, 197, 1273.
10. (b) Ito, K.; Inoue, K.; Yamashita, Y. Makromol. Chem. 1970, 139, 153.
11. (c) Lee, C. W.; Urakawa, R.; Kimura, Y. Macromol. Chem. Phys. 1997, 198, 1109.
12. (d) Nakayama, A.; Kawasaki, N.; Aiba, S.; Maeda, Y.; Arvanitoyannia, I.; Yamamoto, N. Polymer 1998, 39, 1213.
13. (e) Agarwal, S.; Karl, M.; Anfang, S.; Dehnicke, K.; Greiner, A. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.). 1998, 39, 361.
14. (f) Nishiura, M.; Hou, Z.; Koizumi, T.; Imamoto, T.; Wakatsuki, Y. Macromolecules 1999, 32, 8243.
15. (g) Bhaw-Luximon, A.; Jhurry, D.; Motala-Timol, S.; Lochee, Y. Macromol. Symp. 2006, i, 60.
16. (h) Mas, C.; Ramais, X.; Sullan, J. M.; Manteion, A.; Serra, A. J. Polymer Sci., Part A, Polym. Chem. 2003, 41, 2794.
17. (i) Lee, C. W.; Urakawa, R.; Kimura, Y. Macromol. Chem Phys. 1997, 198, 1109.
18. (j) Fukuzaki, H.; Aiba, Y.; Yoshida, M.; Asano, M.; Kumakura, M. Makromol. Chem. 1989, 190, 1553.
19. (k) Kricheldorf, H. R.; Mang, T.; Jonte, J. M. Eur. Polym. J. 1982, 18, 803.
20. (l) Duda, A.; Penczek, S. Biopolymers. Vol. 3b: Polyesters II-Properties and Chemical Synthesis; Steinbuchel, A., Doi, Y., Eds.; Wiley-VCH: Weinheim, 2001; Chapter 12.
21. Nobes, G. A. R.; Kazlauskas, R. J.; Marchessault, R. H. Macromolecules 1996, 29, 4829.
22. (a) Su, F.; Iwata, T.; Tanaka, F.; Doi, Y. Macromolecules 2003, 36, 6401.
23. (b) Kim, K. J.; Doi, Y.; Abe, H.; Martin, D. P. Polym. Deg. Stab. 2006, 91, 2333.
24. (c) Martin, D. P.; Williams, S. F. Biochem. Eng. J. 2003, 16, 97.
25. (d) Moore, T.; Adhikan, R.; Gunatillake, P. Biomaterials 2005, 26, 3671.
26. (a) Leitao, M. L.; Pilcher, G.; Meng-Yan, Y.; Brown, J. M.; Conn, A.D. J. Chem. Thermodyn. 1990, 22, 885.
27. (b) Saiyasombat, W; Molloy, R.; Nicholson, T. M.; Johnson, A. F.; Ward I. M.; Poshyachinda, S. Polymer 1998, 39, 5581.
28. (c) Wiberg, K. B.; Waldron, R. F. J. Am. Chem. Soc. 1991, 113, 7697.
29. (d) Bach, R.; Dmitrenko, O. J. Am. Chem. Soc. 2006, 128, 4598.
30. (a) Blom, C. E.; Guenthard, H. H. Chem. Phys. Lett. 1981, 84, 267.
31. (b) Arnett, E. M.; Harrelson, J. A. J. Am. Chem. Soc. 1987, 109, 809.
32. (c) Kyoungrim, B.; Mo, Y.; Gao, J. J. Am. Chem. Soc. 2001, 123, 3974.
33. Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870.
34. (a) Wiberg, K. B.; Wong, M. W. J. Am. Chem. Soc. 1993, 115, 1078.
35. (b) Evanseck, J. D.; Houk, K. N., Briggs, J. M.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 10630.
36. Huisgen, R.; Ott, H. Tetrahedron. 1959, 6, 253.
37. Frisch, M. J.; et al. Gaussian 03, Revision C02; Gaussian, Inc.; Pitsburgh, PA, 2003.
38. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
39. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
40. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 23, 213.
41. (a) Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532.
42. (b) (a) Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822.
43. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
44. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
45. Cramer, C. J. In Essentials of Computational Chemistry Theories and Models, 2nd ed.; Wiley: New York, 2005.
46. (a) Miertus, M.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
47. (b) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239.
48. (a) Alemán, C.; Casanovas, J.; Hall, H. K., Jr. J. Org. Chem. 2005, 70, 2950.
49. (b) Alemán, C.; Casanovas, J.; Hall, H. K., Jr. J. Org. Chem. 2005, 70, 7731.
50. (a) Navarro, E.; Alemán, C.; Puiggalí, J. J. Am. Chem. Soc. 1995, 117, 7307.
51. (b) Alemán, C.; Navarro, E.; Puiggalí, J. J. Org. Chem. 1995, 60, 6135.
52. (c) Navarro, E.; Tereshko, V.; Subirana, J. A.; Puiggalí, J. Biopolymers 1995, 36, 711.
53. (d) Alemán, C.; Navarro, E.; Puiggalí, J. J. Peptide Sci. 1996, 2, 364.
54. (e) Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Phys. Chem. A 2000, 104, 5115.
55. Alemán, C.; Puiggalí, J. J. Org. Chem. 1997, 101, 3441.
56. Alemán, C.; Navarro, E.; Puiggalí, J. J. Phys. Chem. 1996, 100, 16131.
57. Brown, R. F.; van Gulick, N. M. J. Org. Chem. 1956, 21, 1046-1049.
58. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858-5865.
59. Allinger, N. L.; Zalkow, V. E. J. Org. Chem. 1960, 25, 701.
60. Mark, H. F., Bikales, N. M., Overberger, C. G., Mengen, G., Kroschwitz, G. J., Eds. Encyclopedia of Polymer Science and Engineering, 2nd ed.; Wiley: New York, 1988; Vol. 12.
61. (b) Alemán, C. Biopolymers 1994, 34, 841.
62. (a) Casanovas, J.; Alemán, C. J. Comput. Aided Mol. Design 1994, 8, 441.
63. (b) Alemán, C. Biopolymers 1994, 34, 841.
64. Estropov, A. A.; Lebedev, B. V.; Kulagina, T. G.; Lebedev, N. K. Vysocko, Soed. Ser A 1982, 24, 568;
65. Chem. Abstr. 1982, 96, 218273.
66. Save, M.; Schappacher, M.; Soum, A. Macromol Chem. Phys. 2002 203 889.