Toward an understanding of the catalytic role of hydrogen-bond donor solvents in the hetero-Diels - Alder reaction between acetone and butadiene derivative

Journal of Physical Chemistry A

Volumn 109, Issue 45, 2005, Pages 10438-10444

  Polo, Victor ^a   Domingo, Luis R ^b   Andrés, Juan ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGEN BONDS; NITROGEN COMPOUNDS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS; SOLVENTS;

CHLOROFORM; CHLOROMETHANE; DICHLOROMETHANE; HYDROGEN-BOND DONOR;

CATALYSTS;

1,3 BUTADIENE DERIVATIVE; ACETONE; ETHER DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; QUANTUM THEORY; SYNTHESIS;

ACETONE; BUTADIENES; CATALYSIS; ETHERS; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; QUANTUM THEORY; SOLVENTS;

EID: 28144436336     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp054048g     Document Type: Article

References (101)

1. Sutor, D. J. J. Chem. Soc. 1963, 1105.
2. (a) Green, R. D. Hydrogen Bonding by CH Groups; Macmillan: London, 1974.
3. (b) Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Saunders: M. J. Am. Chem. Soc. 1991, 113, 971.
4. (c) Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1990, 454.
5. (d) Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1992, 114, 7123.
6. (e) Steiner, T.; Saenger, W. Acta Crystallogr. 1992, B48, 819.
7. (f) Steiner, T. Crystallogr. Rev. 1996, 6, 1.
8. (g) Chaney, J. D.; Goss, C. R.; Foiling, K.; Santarsiero, B. D.; Hollingsworth, M. D. J. Am. Chem. Soc. 1996, 118, 9432.
9. (h) Steiner, T.; Kanters, J. A.; Kroon, J. Chem. Commun. 1996, 1277.
10. (i) Kariuki, B. M.; Harris, K. D. M.; Philp, D.; Robinson, J. M. A. J. Am. Chem. Soc. 1997, 119, 12679.
11. (j) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, U.K., 2001.
12. (k) Jeffrey, G. A. J. Mol. Struct. 1999, 486, 293.
13. (l) Steiner, T. J. Phys. Chem. A 2000, 104, 433.
14. (m) Swamy, K. C. K.; Kumaraswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642.
15. (n) Ribeiro-Claro, P. J. A.; Drew, M. G. B.; Felix, V. Chem. Phys. Lett. 2002, 356, 318.
16. (a) Houk, K. N.; Menzer, S.; Newton, S. P.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 1479.
17. (b) Mehta, G.; Vidya, R. J. Org. Chem. 2000, 65, 3497.
18. (a) Metzger, S.; Lippert, B. J. Am. Chem. Soc. 1996, 118, 12467.
19. (b) Sigel, R. K. O.; Freisinger, E.; Metzger, S.; Lippert, B. J. Am. Chem. Soc. 1998, 120, 12000.
20. (c) Hobza, P.; Sponer, J.; Cubero, E.; Orozco, M.; Luque, F. J. J. Phys. Chem. B 2000, 104, 6286 and references therein.
21. (d) Hocquet, A.; Leulliot, N.; Ghomi, M. J. Phys. Chem. B 2000, 104, 4560.
22. (a) Schuster, T.; Kurz, M.; Gobel, M. W., J. Org. Chem. 2000, 65, 1697.
23. (b) Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 9662.
24. (c) See the review: Schreiner, P. R., Chem. Soc. Rev. 2003, 32, 289.
25. (d) Domingo, L. R.; Andres, J. J. Org. Chem. 2003, 68, 8662.
26. (a) Jorgensen, K. A. Eur. J. Org. Chem. 2004, 10, 2093.
27. (b) Wang, H. M.; Wang, Y.; Han, K. L.; Peng, X. J. J. Org. Chem. 2005, 70, 4910.
28. Butler, R. N.; Cunningham, W. J.; Coyne, A. G.; Burke, L. A. J. Am. Chem. Soc. 2004, 126, 11923.
29. Mucsi, Z.: Szabo, A.; Hermecz, I.; Kucsman, A.; Csizmadia, I. G. J. Am. Chem. Soc. 2005, 127, 7615.
30. Boger, D. L.; Weinred, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987; Vol. 47.
31. Tietze, L. F.: Kettschau, G. Stereosel. Heterocycl. Synth. 1997, 189, 1.
32. (a) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250.
33. Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1987, 15, 5.
34. (b) Kametani, T.; Hibino, S. Adv. Heterocycl. Chem. 1987, 42, 245.
35. (c) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol.2, p 661.
36. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
37. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, U.K., 1997.
38. Grabowski, S. J. J. Phys. Chem. A 2001, 105, 10739.
39. For instance, see the reviews: Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163.
40. Calhorda, M. J. Chem. Commun. 2000, 10, 801.
41. Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253.
42. (a) Bader, R. F. W. Acc. Chem. Res. 1985, 18, 9.
43. (b) Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Claredon Press: Oxford, U.K., 1990.
44. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397.
45. (a) Silvi, B.; Savin, A. Nature 1994, 371, 683.
46. (b) Savin, A.; Becke, A. D.; Flad, J.; Nesper, R.; Preuss, H.; Vonschnering, H. G. Angew. Chem., Int. Ed. Engl. 1991, 103, 421.
47. (c) Savin, A.; Jepsen, O.; Flad, J.; Andersen, O. K.; Preuss, H.; Vonschnering, H. G. Angew. Chem., Int. Ed. Engl. 1992, 104, 186.
48. (d) Savin, A.; Silvi, B.; Colonna, F. Can. J. Chem. 1996, 74, 1088.
49. (a) Popelier, P. L. A. Atoms in Molecules. An Introduction; Prentice Hall: Upper Saddle River, NJ, 2000.
50. (b) Popelier, P. L. A.; Aicken, F.; O'Brien, S. E. Chemical Modelling: Applications and Theory; The Royal Society of Chemistry: London, 2000; Vol. 1, Chapter 3.
51. (c) Popelier, P. L. A.; Smith, P. J. Chemical Modelling: Applications and Theory; The Royal Society of Chemistry: London, 2002; Vol. 2, Chapter 8.
52. (d) Popelier, P. L. A.; Aicken, F. M.; O'Brien, S. E. In Chemical Modelling: Applications and Theory; The Royal Society of Chemistry: London, 2000; Vol. 1, Chapter 3.
53. (a) Berski, S.; Andres, J.; Silvi, B.; Domingo, L. R. J. Phys. Chem. A 2003, 107, 6014.
54. (b) Polo, V.; Andres, J.; Castillo, R.; Berski, S.; Silvi, B. Chem.-Eur. J. 2004, 10, 5165.
55. (c) Santos, J. C.; Andres, J.; Aizman, A.; Fuentealba, P.; Polo, V. J. Phys. Chem. A 2005, 109, 3687.
56. (d) Santos, J. C.; Polo, V.; Andres, J. Chem. Phys. Lett. 2005, 406, 393.
57. (e) Polo, V.; Andres, J. J. Comput. Chem. 2005, 26, 1427.
58. (a) Santos, J. C.; Andres, J.; Aizman, A.; Fuentealba, P. J. Chem. Theor. Comput. 2005, 1, 83.
59. (b) Poater, J.; Duran, M.; Sola, M.; Silvi, B. Chem. Rev. 2005, 105, 3911.
60. See, for example: (a) Michelini, M. D.; Sicilia, E.; Russo, N.; Alikhani, M. E.; Silvi, B. J. Phys. Chem. A 2003, 107, 4862.
61. (b) Chamorro, E.; Notario, R. J. Phys. Chem. A 2004, 108, 4099.
62. Fuster, F.; Silvi, B.; Berski, S.; Latajka, Z. J. Mol. Struct. 2000, 555, 75.
63. Fuster, F.; Silvi, B. Theor. Chem. Acc. 2000, 104, 13.
64. (a) Morokuma, K. J. Chem. Phys. 1971, 55, 1236.
65. (b) Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 325.
66. (a) Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1.
67. (b) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755.
68. (c) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558.
69. Bickelhaupt, F. M., Baerends, E. J. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd D. B., Eds.; Wiley-VCH: New York, 2000; Vol. 15, p 1.
70. Jeziorski, B.; Kolos, W. Int. J. Quantum Chem. 1977, 12, 91.
71. van der Vaart, A.; Merz, K. M. J. Phys. Chem. A 1999, 103, 3321.
72. Glendening, E. D.; Streitwieser, A. J. Chem. Phys. 1994, 100, 2900.
73. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
74. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
75. (c) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Ref. B 1988, 37, 785.
76. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
77. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
78. 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.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; 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 C.02; Gaussian, Inc.: Pittsburgh, PA, 2004.
79. Ortiz, J. C.; Bo, C. XAIM 1.0.; Universitat Rovira i Virgili, Tarragona, Spain, 1998.
80. Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. TopMoD Package; Université Pierre et Marie Curie, Paris, 1997.
81. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. MOLEKEL 4.0; J. Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
82. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
83. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: Oxford, U.K., 1997.
84. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
85. Grabowski, S. J. J. Phys. Chem. A 2001, 105, 10739.
86. Jenkins, S.; Morrison, I. Chem. Phys. Lett. 2000, 317, 97.
87. (a) Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170.
88. (b) Espinosa. E.; Lecomte, C.; Molins, E. Chem. Phys. Lett. 1999, 300, 745.
89. (c) Espinosa, E.; Molins, E. J. Chem. Phys. 2000, 113, 5686.
90. (d) Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. Chem. Phys. Lett. 2001, 336, 457.
91. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973.
92. In the literature discussion of hydrogen bonding, the terms donor and acceptor are used in two different contexts. "HB donor" is the X-H part of the X-H⋯Y complex, where Y is called "HB acceptor". However, if the hyperconjugative flow of electrons in a Lewis-type electron donor/electron acceptor interaction is described, then σ*(X-H) is a Lewis (hyperconjugative) acceptor, and the lone pair of Y is a Lewis (hyperconjugative) donor. HB acceptors are, in fact, electron donors in charge-transfer hyperconjugative (cT) n(Y) →σ*(X-H) interactions.
93. Bent, H. A. Chem. Rev. 1961, 61, 275.
94. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
95. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747.
96. (a) Grabowski, S. J. Chem. Phys. Lett. 2001, 338, 361.
97. (b) Grabowski, S. J. J. Phys. Chem. A 2001, 105, 10739.
98. Flaig, R.; Koritsanszky, T.; Dittrich, B.; Wagner, A.; Luger, P. J. Am. Chem. Soc. 2002, 124, 3407.
99. Arnold, W. D.; Oldfield, E. J. Am. Chem. Soc. 2000, 122, 12835.
100. Similar results were obtained employing the 6-311+G(2d,2p) basis set. Note that these values are at the limit of accuracy of the TopMod program.
101. Lepetit, C.; Silvi, B.; Chauvin, R. J. Phys. Chem. A 2003, 107, 464.