Urea metal-organic frameworks as effective and size-selective hydrogen-bond catalysts

Journal of the American Chemical Society

Volumn 134, Issue 7, 2012, Pages 3334-3337

  Roberts, John M ^a,b   Fini, Branden M ^a,b   Sarjeant, Amy A ^a   Farha, Omar K ^a   Hupp, Joseph T ^a   Scheidt, Karl A ^a,b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION BEHAVIOR; BIPYRIDINES; GENERAL SOLUTIONS; HETEROGENEOUS CATALYST; HYDROGEN BONDINGS; METAL ORGANIC FRAMEWORK; MICROPOROUS; NITROALKENES; SELF-RECOGNITION; SIZE-SELECTIVE; SOLVOTHERMAL CONDITIONS; SPATIAL ISOLATION;

BEHAVIORAL RESEARCH; CATALYSIS; CATALYSTS; FRIEDEL-CRAFTS REACTION; HYDROGEN; JAVA PROGRAMMING LANGUAGE; REACTION RATES; UREA;

METABOLISM;

ALKENE DERIVATIVE; METAL ORGANIC FRAMEWORK; PYRROLE DERIVATIVE; UREA;

ARTICLE; CATALYST; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; HYDROGEN BOND; PARTICLE SIZE; SOLVATION;

CATALYSIS; HYDROGEN BONDING; METALS; ORGANOMETALLIC COMPOUNDS; PYRIDINES; UREA; ZINC;

EID: 84857434860     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2108118     Document Type: Article

References (62)

1. Férey, G. Chem. Soc. Rev. 2008, 37, 191
2. Horike, S.; Shimomura, S.; Kitagawa, S. Nat. Chem. 2009, 1, 695
3. O'Keeffe, M.; Yaghi, O. M. Chem. Rev. 2011, 10.1021/cr200205j
4. Murray, L. J.; Dincǎ, M.; Long, J. R. Chem. Soc. Rev. 2009, 38, 1294
5. Farha, O. K.; Yazaydin, A. O.; Eryazici, I.; Malliakas, C. D.; Hauser, B. G.; Kanatzidis, M. G.; Nguyen, S. T.; Snurr, R. Q.; Hupp, J. T. Nat. Chem. 2010, 2, 944
6. Furukawa, H.; Ko, N.; Go, Y. B.; Aratani, N.; Choi, S. B.; Choi, E.; Yazaydin, A. O.; Snurr, R. Q.; O'Keeffe, M.; Kim, J.; Yaghi, O. M. Science 2010, 329, 424
7. Thallapally, P. K.; Tian, J.; Kishan, M. R.; Fernandez, C. A.; Dalgarno, S. J.; McGrail, P. B.; Warren, J. E.; Atwood, J. L. J. Am. Chem. Soc. 2008, 130, 16842
8. Sun, L. X.; Song, L. F.; Jiang, C. H.; Jiao, C. L.; Zhang, J. A.; Xu, F.; You, W. S.; Wang, Z. G.; Zhao, J. J. Cryst. Growth Des. 2010, 10, 5020
9. Achmann, S.; Hagen, G.; Kita, J.; Malkowsky, I. M.; Kiener, C.; Moos, R. Sensors 2009, 9, 1574
10. Morris, R. E.; McKinlay, A. C.; Horcajada, P.; Férey, G.; Gref, R.; Couvreur, P.; Serre, C. Angew. Chem., Int. Ed. 2010, 49, 6260
11. Kent, C. A.; Liu, D.; Ma, L.; Papanikolas, J. M.; Meyer, T. J.; Lin, W. J. Am. Chem. Soc. 2011, 133, 12940
12. Lee, C. Y.; Farha, O. K.; Hong, B. J.; Sarjeant, A. A.; Nguyen, S. T.; Hupp, J. T. J. Am. Chem. Soc. 2011, 133, 15858
13. Lee, J.; Farha, O. K.; Roberts, J.; Scheidt, K. A.; Nguyen, S. T.; Hupp, J. T. Chem. Soc. Rev. 2009, 38, 1450
14. Lee, J. Y.; Roberts, J. M.; Farha, O. K.; Sarjeant, A. A.; Scheidt, K. A.; Hupp, J. T. Inorg. Chem. 2009, 48, 9971
15. Roberts, J. M.; Farha, O. K.; Sarjeant, A. A.; Hupp, J. T.; Scheidt, K. A. Cryst. Growth Des. 2011, 11, 4747
16. Shultz, A. M.; Sarjeant, A. A.; Farha, O. K.; Hupp, J. T.; Nguyen, S. T. J. Am. Chem. Soc. 2011, 133, 13252
17. Farha, O. K.; Shultz, A. M.; Sarjeant, A. A.; Nguyen, S. T.; Hupp, J. T. J. Am. Chem. Soc. 2011, 133, 5652
18. Shultz, A. M.; Farha, O. K.; Adhikari, D.; Sarjeant, A. A.; Hupp, J. T.; Nguyen, S. T. Inorg. Chem. 2011, 50, 3174
19. Banerjee, M.; Das, S.; Yoon, M.; Choi, H. J.; Hyun, M. H.; Park, S. M.; Seo, G.; Kim, K. J. Am. Chem. Soc. 2009, 131, 7524
20. Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. J. Am. Chem. Soc. 2010, 132, 14321
21. Lun, D. J.; Waterhouse, G. I. N.; Telfer, S. G. J. Am. Chem. Soc. 2011, 133, 5806
22. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289
23. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
24. Jacobsen, E. N.; Doyle, A. G. Chem. Rev. 2007, 107, 5713
25. Connon, S. J. Chem. Commun. 2008, 2499
26. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187
27. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901
28. Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217
29. Etter, M. C.; Reutzel, S. M. J. Am. Chem. Soc. 1991, 113, 2586
30. Smith, P. J.; Kim, E.-i.; Wilcox, C. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1648
31. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369
32. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259
33. Jacobsen, E. N.; Wenzel, A. G. J. Am. Chem. Soc. 2002, 124, 12964
34. Dessole, G.; Gabriella, D.; Herrera, R. P.; Riccia, A. Synlett 2004, 2374
35. Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 3830
36. Deshapan, S. V.; Meredith, C. C.; Pasterna, R. A. Acta Crystallogr. 1968, B24, 1396
37. Stankovic, S.; Andreetti, G. D. Acta Crystallogr. 1978, B34, 3787
38. George, S.; Nangia, A.; Lynch, V. M. Acta Crystallogr. 2001, C57, 777
39. George, S.; Nangia, A. Acta Crystallogr. 2003, E59, 901
40. Slawin, A. M. Z.; Lawson, J.; Storey, J. M. D.; Harrison, W. T. A. Acta Crystallogr. 2007, E63, 2925
41. 3,5-Dicarboxy-substituted arylureas (and related esters) are poor materials for comparison since these esters prevent dimerization through steric "shielding". Modeling with the aryl rings aligned in-plane with the urea carbonyl group clearly showed that the ester substituents of one urea engender destablizing/unfavorable van der Waals interactions with a second 3,5-dicarboxyurea ester before the carbonyl group of one molecule is close enough to the NH groups of a second urea molecule for intermolecular self-quenching.
42. Custelcean, R.; Moyer, B. A.; Hay, B. P. Chem. Commun. 2005, 5971
43. Custelcean, R.; Haverlock, T. J.; Moyer, B. A. Inorg. Chem. 2006, 45, 6446
44. Custelcean, R.; Moyer, B. A.; Bryantsev, V. S.; Hay, B. P. Cryst. Growth Des. 2006, 6, 555
45. Das, A.; Kumar, D. K.; Dastidar, P. New J. Chem. 2006, 30, 1267
46. Vilar, R.; Diaz, P.; Benet-Buchholz, J.; White, A. J. P. Inorg. Chem. 2006, 45, 1617
47. Custelcean, R.; Moyer, B. A. Eur. J. Inorg. Chem. 2007, 1321
48. Custelcean, R.; Sellin, V.; Moyer, B. A. Chem. Commun. 2007, 1541
49. Custelcean, R.; Remy, P.; Bonnesen, P. V.; Jiang, D. E.; Moyer, B. A. Angew. Chem., Int. Ed. 2008, 47, 1866
50. Dastidar, P.; Adarsh, N. N.; Kumar, D. K. CrystEngComm 2008, 10, 1565
51. Cohen, S. M.; Garibay, S. J.; Wang, Z. Q.; Tanabe, K. K. Inorg. Chem. 2009, 48, 7341
52. Custelcean, R.; Bock, A.; Moyer, B. A. J. Am. Chem. Soc. 2010, 132, 7177
53. Custelcean, R.; Rajbanshi, A.; Moyer, B. A. Cryst. Growth Des. 2011, 11, 2702
54. Li, J.; Lan, A. J.; Li, K. H.; Wu, H. H.; Olson, D. H.; Emge, T. J.; Ki, W.; Hong, M. C. Angew. Chem., Int. Ed. 2009, 48, 2334
55. García, J. M.; Oiarbide, M.; Palomo, C.; Bartoli, G.; Melchiorre, P.; Bernardi, L.; Ricci, A. In Catalytic Asymmetric Friedel-Crafts Alkylations; Wiley-VCH: Weinheim, Germany, 2009; pp 17-99.
56. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370
57. Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009
58. Bonini, B. F.; Capito, E.; Comes-Franchini, M.; Fochi, M.; Riccia, A.; Zwanenburg, B. Tetrahedron: Asymmetry 2006, 17, 3135
59. Blay, G.; Fernandez, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9, 2601
60. Li, G. L.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065
61. Trost, B. M.; Muller, C. J. Am. Chem. Soc. 2008, 130, 2438
62. Yokoyama, N.; Arai, T. Chem. Commun. 2009, 3285