Intramolecular hydrogen bond strength and pKa determination of N,N′-disubstituted imidazole-4,5-dicarboxamides

Organic Letters

Volumn 7, Issue 1, 2005, Pages 135-138

  Rush, Jeremy R ^a   Sandstrom, Stacey L ^a   Yang, Jianqing ^a   Davis, Rebecca ^a   Prakash, Om ^a   Baures, Paul W ^a,b  

^a KANSAS STATE UNIVERSITY   (United States)

^b BOWDOIN COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BASE; DIMETHYL SULFOXIDE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; ELECTRON; HYDROGEN BOND; MOLECULE; STRENGTH; SUBSTITUTION REACTION; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

HYDROGEN BONDING; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

EID: 12344250059     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047812a     Document Type: Article

References (19)

1. Baures, P. W. Org. Lett. 1999, 1, 249.
2. VanCompernolle, S.; Wiznycia, A. V.; Rush, J. R.; Dhanasekaran, M.; Baures, P. W.; Todd, S. C. Virology 2003, 314, 371.
3. Baures, P. W.; Rush, J. R.; Wiznycia, A. V.; Desper, J.; Helfrich, B. A.; Beatty, A. M. Cryst. Growth Des. 2002, 2, 653.
4. Yasuda, N.; Nakamura, A.; Tsuboi, M. J. Heterocycl. Chem. 1987, 24, 303.
5. Aleksandrova, I. Ya.; Gol'dfarb, V. L.; Khromov-Borisov, N. V.; Brovtsyna, N. B. Zh. Org. Khim. 1976, 12, 1109.
6. Bouck, K. J.; Rasmussen, P. G. Macromolecules 1993, 26, 2077.
7. Wiznycia, A. V.; Rush, J. R.; Baures, P. W. J. Org. Chem. 2004, 69, 8489.
8. Wiznycia, A. V.; Helfrich, B. A.; Baures, P. W. J. Org. Chem. 2002, 67, 7151.
9. Jones, R. G. J. Am. Chem. Soc. 1952, 74, 1085.
10. Spartan '02; Wave function Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612
11. See Supporting Information.
12. Van Geet, A. L. Anal. Chem. 1968, 40, 2227.
13. Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
14. Lin, J.; Frey, P. A. J. Am. Chem. Soc. 2000, 122, 11258.
15. 2O. The difference between pH and pD is small relative to the highlighted differences.
16. Markley, J. L. Acc. Chem. Res. 1975, 8, 70.
17. Shim, J. H.; Wall, M.; Benkovic, S. J. J. Am. Chem. Soc. 2001, 123, 4687.
18. 3).
19. Yamasaki, R.; Tanatani, A,.; Azumaya, I.; Saito, S.; Yamaguchi, K.; Kagechika, H. Org. Lett. 2003, 5, 1265.