Stable three-center hydrogen bonding in a partially rigidified structure

Chemistry - A European Journal

Volumn 7, Issue 20, 2001, Pages 4352-4357

  Parra, Rubén D ^b   Zeng, Huaqiang ^a   Zhu, Jin ^a   Zheng, Chong ^c   Zeng, Xiao Cheng ^b   Gong, Bing ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^c NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Ab initio calculations; Cooperative phenomena; Hydrogen bonds; Three center bonds

Indexed keywords

INFRARED SPECTROSCOPY; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

STRUCTURAL ISOMERS;

HYDROGEN BONDS;

AMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

AMIDES; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, INFRARED;

EID: 0035886828     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011015)7:20<4352::AID-CHEM4352>3.0.CO;2-L     Document Type: Article

References (57)

1. a) G. A. Jeffrey, W. Sanger, Hydrogen Bonding in Biological Structures, Springer, Berlin, Heidelberg, 1994;
2. b) G. A. Jeffrey, Crystallogr. Rev. 1995, 4, 213;
3. c) G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997;
4. d) S. Scheiner, Hydrogen Bonding: A Theoretical Perspective, Oxford University Press, New York, 1997.
5. a) R. Parthasarathy, Acta Crystallogr. Sect. C 1969, 25, 509;
6. b) P. G. Jönsson, A. Kvick, Acta Crystallogr. Sect. B 1972, 28, 1827;
7. c) G. A. Jeffrey, S. Takagi, Acc. Chem. Res. 1978, 11, 264;
8. d) C. H. Görbitz, M. C. Etter, J. Chem. Soc. Perkin Trans. 2 1992, 131;
9. e) C. Huang, L. A. Cabell, E. A. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778.
10. a) H. C. M. Nelson, J. T. Finch, B. F. Luisi, A. Klug, Nature 1987, 330, 221;
11. b) J. E. Koehler, W. Saenger, W. F. van Gunsteren, J. Biomol. Struct. Dyn. 1988, 6, 181;
12. c) R. Preissner, U. Egner, W. Saenger, FEBS Lett. 1991, 288, 192;
13. d) D. S. Goodsell, M. L. Kopka, R. E. Dickerson, Biochemistry 1995, 34, 4983.
14. S. C. Zimmerman, T. J. Murray, Tetrahedron Lett. 1994, 35, 4077.
15. a) J. H. Yang, S. H. Gellman, J. Am. Chem. Soc. 1998, 120, 9090;
16. b) J. H. Yang, L. A. Christianson, S. H. Gellman, Org. Lett. 1999, 1, 11.
17. S. F. Bureiko, N. S. Glubev, K. Pihlaja, J. Mol. Struct. 1999, 297.
18. a) I. Rozas, I. Alkorta, J. Elguero, J. Phys. Chem. A 1998, 102, 9925;
19. b) Y. D. Wu, D. P. Wang, K. W. K. Chan, D. Yang, J. Am. Chem. Soc. 1999, 121, 11189.
20. F. J. Martínez-Martínez, I. I. Padilla-Martínez, M. A. Brito, E. D. Geniz, R. C. Rojas, J. B. R. Saavedra, H. Höpfl, M. Tlahuextl, R. Contreras, J. Chem. Soc. Perkin Trans. 2 1998, 401.
21. a) H. S. Frank, W. Y. Wen, Discuss. Faraday Soc. 1957, 24, 133;
22. b) J. E. Del Bene, J. A. Pople, Chem. Phys. Lett. 1969, 4, 426;
23. c) G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, 1999, p. 80;
24. d) P. Schuster, P. Wolschann, in Hydrogen Bond Research, Springer, Wien, 1999, p. 6;
25. e) H. Guo, S. Sirois, E. I. Proynov, D. R. Salahub, in Theoretical Treatment of Hydrogen Bonding, Wiley, New York, 1997, p. 64.
26. L. Ojamäe, K. Hermansson, J. Phys. Chem. 1994, 98, 4271.
27. a) R. D. Parra, X. C Zeng, J. Chem. Phys. 1999, 110, 6329;
28. b) G. Larsen, Z. K. Ismail, B. Herreros, R. D. Parra, J. Phys. Chem. A 1998, 102, 4734;
29. c) O. Mó, M. Yáñez, J. Elguero, J. Chem. Phys. 1997, 107, 3592;
30. c) X. Duan, S. Scheiner, Int. J. Quantum Chem. Quantum Biol. Symp. 1993, 20, 181;
31. d) P. Kollman, J. Am. Chem. Soc. 1977, 99, 4875.
32. G. Gilli, F. Belluci, V. Ferreti, V. Bertolasi, J. Am. Chem. Soc. 1989, 111, 1023.
33. a) S. Scheiner, Hydrogen Bonding: A Theoretical Perspective, Oxford University Press, New York, 1997, Chapters, and references therein;
34. b) A. Simperler, W. Mikenda, in Hydrogen Bond Research, Springer, Wien, 1999, p. 66;
35. c) J. S. Craw, G. B. Bacskay, J. Chem. Soc. Faraday Trans. 1992, 88, 2315;
36. d) S. Millefiori, S. Di Bella, J. Chem. Soc. Faraday Trans. 1991, 87, 1297.
37. a) P. L. Huyskens, J. Am. Chem. Soc. 1977, 99, 2578;
38. b) H. Kleeberg, D. Klein, W. A. P. Luck, J. Phys. Chem. 1987, 91, 3200.
39. a) S. H. Gellman, G. P. Dado, G.-B. Liang, B. R. Adams, J. Am. Chem. Soc. 1991, 113, 1164;
40. b) W. L. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2008.
41. a) J. Zhu, R. D. Parra, H. Zeng, E. Skrzypczak-Jankun, X. C. Zeng, B. Gong, J. Am. Chem. Soc. 2000, 122, 4219;
42. b) H. Zeng, R. Miller, R. A. Flowers II, B. Gong, J. Am. Chem. Soc. 2000, 122, 2635.
43. J. C. Davis, Jr. Adv. Magn. Reson. 1970, 4, 201.
44. a) M. Tichy, Adv. Org. Chem. 1965, 5, 115;
45. b) H. Ratajczak, W. J. Orville-Thomas, J. Mol. Struct. 1968, 7, 449;
46. c) M. C. R. Symons, Chem. Soc. Rev. 1983, 12, 1;
47. d) A. C. Legon, Chem. Soc. Rev. 1990, 19, 197.
48. R. Parthasarathy, Acta Crystallogr. Sect. B 1969, 25, 509.
49. a) J. Pranata, S. G. Wierschke, W. L. Jorgensen, J. Am. Chem. Soc. 1991, 113, 2810;
50. b) T. J. Murray, S. C. Zimmermann, J. Am. Chem. Soc. 1992, 114, 4010.
51. G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441.
52. G. M. Sheldrick, SHELXTL Version 5, Siemens Analytical Instruments Inc.: Madison, Wisconsin, 1994.
53. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 52, 115.
54. Y. Le Page, J. Appl. Crystallogr. 1987, 20, 264.
55. A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, C34.
56. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian98 (Revision A.3), Gaussian, Inc., Pittsburgh PA, 1998.
57. B. J. Foresman, Æ. Frish, Exploring Chemistry with Electronic Structure Methods, 2nd ed., 1996, p. 64.