Hydrogen bonding in ortho-substituted arylamides: The influence of protic solvents

Journal of Physical Chemistry B

Volumn 113, Issue 20, 2009, Pages 7041-7044

  Liu, Zhiwei ^a   Remsing, Richard C ^a   Liu, Dahui ^b   Moyna, Guillermo ^a   Pophristic, Vojislava ^a  

^a UNIVERSITY OF THE SCIENCES   (United States)

^b PolyMedix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILES; HYDROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS;

APROTIC; AQUEOUS ENVIRONMENT; ARYLAMIDE; BUILDING BLOCK; COMPUTATIONAL APPROACH; CONFORMATIONAL PREFERENCES; CUMULATIVE NUMBER; FOLDAMERS; H-BONDING; H-BONDS; HYDROGEN BONDINGS; INTRAMOLECULAR HYDROGEN BONDING; METHOXY; PROTIC SOLVENTS; SOLVENT EFFECTS; STABILIZING EFFECTS;

HYDROGEN BONDS;

EID: 67650045882     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp902155j     Document Type: Article

References (33)

1. (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
2. (b) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68.
3. (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem Rev. 2001, 101, 3893-4011.
4. (d) Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem Biol. 2001, 5, 650-653.
5. (e) Schmuck, C. Angew. Chem Int. Ed. 2003, 42, 2448-2452.
6. (a) Huc, I. Eur. J. Org. Chem. 2004, 1, 7-29.
7. (b) Li, Z.; Hou, J.; Li, C.; Yi, H. Chem. Asian J. 2006, 1, 766-778.
8. (c) Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Nat. Chem. Biol. 2007, 3, 252-262.
9. (a) Choi, S.; Clements, D. J.; Pophristic, V.; Ivanov, I.; Vemparala, S.; Bennett, J. S.; Klein, M. L.; Winkler, J. D.; DeGrado, W. E. Angew. Chem., Int. Ed. 2005, 44, 6685-6689.
10. (b) Pophristic, V.; Vemparala, S.; Ivanov, I.; Liu, Z. W.; Klein, M. L.; DeGrado, W. F. J. Phys. Chem. B 2006, 110, 3517-3526.
11. Liu, D. H.; Choi, S.; Chen, B.; Doerksen, R. J.; Clements, D. J.; Winkler, J. D.; Klein, M. L.; DeGrado, W. F. Angew. Chem., Int. Ed. 2004, 43, 1158-1162.
12. (a) Gong, B.; Yan, Y. F.; Zeng, H. Q.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607-5608.
13. (b) Zeng, H. Q.; Miller, R. S.; Flowers, R. A.; Gong, B. J. Am. Chem. Soc. 2000, 122, 2635-2644.
14. (c) Gong, B. Synlett 2001, 582-589.
15. (d) Zeng, H. Q.; Yang, X. W.; Flowers, R. A.; Gong, B. J Am Chem. Soc. 2002, 124, 2903-2910.
16. (e) Sanford, A. R.; Yamato, K.; Yang, X. W.; Yuan, L. H.; Han, Y. H.; Gong, B. Eur. J. Biochem. 2004, 271, 1416-1425.
17. (a) Zhu, J.; Parra, R. D.; Zeng, H. Q.; Skrzypczak-Jankun, E.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2000, 122, 4219-4220.
18. (b) Gong, B. Chem. Eur. J. 2001, 7, 4336-4342.
19. (c) Gong, B.; Zeng, H. Q.; Zhu, J.; Yuan, L. H.; Han, Y. H.; Cheng, S. Z.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583-11588.
20. (d) Gong, B. Acc. Chem. Res. 2008, 41, 1376-1386.
21. (a) Yi, H. P.; Li, C.; Hou, J. L.; Jiang, X. K.; Li, Z. T. Tetrahedron 2005, 61, 7974-7980.
22. (b) Li, Z.; Hou, J.; Li, C. Acc.Chem. Res. 2008, 41, 1343-1353.
23. (a) Berl, V.; Huc, I.; Khoury, R. G.; Krische, M. J.; Lehn, J. M. Nature (London) 2000, 407, 720-723.
24. (b) Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J. M. Chem.-Eur. J. 2001, 7, 2810-2820.
25. (c) Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J. M. Chem.-Eur.J. 2001, 7, 2798-2809.
26. (d) Jiang, H; Leger, J. M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448-3449.
27. (e) Jiang, H.; Leger, J. M.; Dolain, C.; Guionneau, P.; Huc, I. Tetrahedron 2003, 59, 8365-8374.
28. Wang, J. M.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 2004, 25, 1157-1174.
29. Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. J. Phys. Chem. 1993, 97, 10269-10280.
30. Stott, K.; Keeler, J.; Van, Q. N.; Shaka, A. J. J. Magn. Reson. 1997, 125, 302-324.
31. Kessler, H.; Griesinger, C.; Lautz, J.; Muller, A.; van Gunsteren, W. F.; Berendsen, H. J. C. J. Am. Chem. Soc. 1998, 110, 3393-3396.
32. (a) Li, M.; Yamato, K.; Ferguson, J. S.; Gong, B. J. Am. Chem. Soc. 2006, 128, 12628-12629.
33. (b) Li, M.; Yamato, K.; Ferguson, J. S.; Singarapu, K. K.; Szyperski, T.; Gong, B. J. Am. Chem Soc. 2008, 130, 491-500.