Dramatic behavioral differences of the copolymerization reactions of 1,4-cyclohexadiene and 1,3-cyclohexadiene oxides with carbon dioxide

Macromolecules

Volumn 48, Issue 6, 2015, Pages 1679-1687

  Darensbourg, Donald J ^a   Chung, Wan Chun ^a   Yeung, Andrew D ^a   Luna, Mireya ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CARBONATION; CATALYSIS; CATALYSTS; CHEMICAL BONDS; COPOLYMERIZATION; COPOLYMERS; CROSSLINKING; CRYSTALLOGRAPHY; POLYCARBONATES; PROPYLENE; TERPOLYMERIZATION;

1 ,4-CYCLOHEXADIENES; ALTERNATING COPOLYMER; CATALYTIC CONDITIONS; COMPUTATIONAL STUDIES; COPOLYMERIZATION REACTIONS; ENHANCED REACTIVITY; ENTHALPY OF REACTION; THIOL-ENE CHEMISTRIES;

X RAY CRYSTALLOGRAPHY;

EID: 84925430676     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.5b00172     Document Type: Article

References (45)

1. Honda, S.; Mori, T.; Goto, H.; Sugimoto, H. Polymer 2014, 55, 4832-4836
2. Darensbourg, D. J.; Chung, W.-C.; Arp, C. J.; Tsai, F.-T.; Kyran, S. J. Macromolecules 2014, 47, 7347-7353
3. Winkler, M.; Romain, C.; Meier, M. A. R.; Williams, C. K. Green Chem. 2015, 17, 300-306
4. Mathers, R. T.; Shreve, M. J.; Meyler, E.; Damodaran, K.; Iwig, D. F.; Kelley, D. J. Macromol. Rapid Commun. 2011, 32, 1338-1342
5. Mutlu, H.; Hafsa, R.; Montenegro, R. E.; Meier, M. A. R. RSC Adv. 2013, 3, 4927-4934
6. Mmongoyo, J. A.; Mgani, Q. A.; Mdachi, S. J. M.; Pogorzelec, P. J.; Cole-Hamilton, D. J. Eur. J. Lipid Sci. Technol. 2012, 114, 1183-1192
7. Darensbourg, D. J.; Chung, W.-C. Polyhedron 2013, 58, 139-143
8. Darensbourg, D. J.; Yeung, A. Y. Polym. Chem. 2015, 6, 1103-1117
9. Demadis, K. D.; Meyer, T. J.; White, P. S. Inorg. Chem. 1998, 37, 3610-3619
10. Lu, X.-B.; Shi, L.; Wang, Y.-M.; Zhang, R.; Zhang, Y.-J.; Peng, X.-J.; Zhang, Z.-C.; Li, B. J. Am. Chem. Soc. 2006, 128, 1664-1674
11. APEX2, version 2009.7-0, Bruker AXS, Inc., Madison, WI, 2007.
12. SAINTPLUS: Program for Reduction of Area Detector Data, 1034 version 6.63, Bruker AXS Inc., Madison, WI, 2007.
13. Sheldrick, G. M. SADABS: Program for Absorption Correction of 1036 Area Detector Frames, Bruker AXS Inc., Madison, WI, 2001.
14. Sheldrick, G. M. SHELXS-97: Program for Crystal Structure 1038 Solution, Universitat Göttingen: Göttingen, Germany, 1997.
15. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure 1040 Refinement, Universitat Göttingen, Göttingen, Germany, 1997.
16. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457
17. Gaussian 09: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian Inc., Wallingford, CT, 2009.
18. Ampac GUI 9, Semichem, Inc., 2008.
19. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.; Zurek, E.; Hutchison, G. R. J. Cheminf. 2012, 4, 17
20. Darensbourg, D. J.; Yeung, A. D. Macromolecules 2013, 46, 83-95
21. Darensbourg, D. J.; Yeung, A. D. Green Chem. 2014, 16, 247-252
22. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827
23. Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996, 104, 2598-2619
24. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
25. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101/1-194101/18
26. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866-872
27. Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193-2218
28. Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94, 6081-6090
29. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532
30. Parthiban, S.; de Oliveira, G.; Martin, J. M. L. J. Phys. Chem. A 2001, 105, 895-904
31. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
32. An alternate synthesis of this epoxide is reported in the literature. Crandall, J. K.; Banks, D. B.; Colyer, R. A.; Watkins, R. J.; Arrington, J. P. J. Org. Chem. 1968, 33, 423-425
33. Koning, C.; Wildeson, J.; Parton, R.; Plum, B.; Steeman, P.; Darensbourg, D. J. Polymer 2001, 42, 3995-4004
34. Darensbourg, D. J.; Wei, S.-H. Macromolecules 2012, 45, 5916-5922
35. Darensbourg, D. J.; Yeung, A. D.; Wei, S.-H. Green Chem. 2013, 15, 1578-1583
36. Diallo, A. K.; Kirillov, E.; Slawinski, M.; Brusson, J.-M.; Guillaumea, S. M.; Carpentier, J.-F. Polym. Chem. 2015, 6, 1961-1971
37. Inoue, S.; Koinuma, H.; Yokoo, Y.; Tsuruta, T. Makromol. Chem. 1971, 143, 97-104
38. Darensbourg, D. J.; Holtcamp, M. W.; Strack, G. E.; Zimmer, M. S.; Niezgoda, S. A.; Rainey, P.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H. J. Am. Chem. Soc. 1999, 121, 107-116
39. Darensbourg, D. J.; Lewis, S. J.; Rodgers, J. L.; Yarbrough, J. C. Inorg. Chem. 2003, 42, 581-589
40. Darensbourg, D. J.; Wilson, S. J. Green Chem. 2012, 14, 2665-2671
41. Dümler, W.; Kirsch, H. Chem. Ber. 1990, 123, 277-283
42. Shi, L.; Lu, X.-B.; Zhang, R.; Peng, X.-J.; Zhang, C.-Q.; Li, J.-F.; Peng, X.-M. Macromolecules 2006, 39, 5679-5685
43. Fineman, M.; Ross, S. D. J. Polym. Sci. 1950, 5, 259-262
44. Darensbourg, D. J.; Tsai, F.-T. Macromolecules 2014, 47, 3806-3813
45. Darensbourg, D. J.; Yeung, A. D. Polym. Chem. 2014, 5, 3949-3962