An ab initio study of intramolecular hydrogen bondings in α-hydroxy ketomethylene dipeptide isostere

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5036-5041

  Kim, Byeang Hyean ^a   Cho, Soo Gyeong ^b   Ha, Tae Kyu ^c  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b Agency for Defence Development   (South Korea)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYACID; CARBONYL DERIVATIVE; DIPEPTIDE DERIVATIVE; HYDROXYL GROUP; KETOL;

ARTICLE; CONFORMATION; ENTROPY; GAS; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; ROTATION; VIBRATION;

EID: 0001627944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982274z     Document Type: Article

References (29)

1. Kim, B. H.; Chung, Y. J.; Ryu, E. J. Tetrahedron Lett. 1993, 34, 8465.
2. Kim, B. H.; Ryu, E. J.; Chung, Y. J. Bioorg. Med. Chem. Lett. 1994, 4, 2799.
3. (a) Kim, D. H.; Choi, K. J.; Chung, Y. J.; Kim, B. H. J. Appl. Phar. 1994, 2, 155.
4. (b) Chung, Y. J.; Kim, D. H.; Choi, K. J.; Kim, B. H. Kor. J. Med. Chem. 1995, 5, 141.
5. (c) Chung, Y. J.; Ryu, E. J.; Keum, G.; Kim, B. H. Bioorg. Med. Chem. 1996, 4, 209.
6. (a) Domínguez, M. J.; González-Muñiz, R.; García-López, M. T. Tetrahedron 1992, 48, 2761.
7. (b) Hoffman, R. V.; Kim, H.-O. Tetrahedron Lett. 1992, 33, 3579.
8. (c) Dondoni, A.; Perrone, D. Tetrahedron Lett. 1992, 33, 7259.
9. (d) García-López, M. T.; González-Muñiz, R.; Harto, J. R. Tetrahedron Lett. 1988, 29, 1577.
10. (e) Holladay, M. W.; Rich, D. H. Tetrahedron Lett. 1983, 24, 4401.
11. (f) Jennigs-White, C.; Almquist, R. G. Tetrahedron Lett. 1982, 23, 2533.
12. (a) Ewenson, A.; Laufer, R.; Chorev, M.; Selinger, Z.; Gilon, C. J. Med. Chem. 1988, 31, 416.
13. (b) Almquist, R. G.; Olsen, C. M.; Uyeno, E. T.; Toll, L. J. Med. Chem. 1984, 27, 115.
14. (c) Almquist, R. G.; Chao, W.-R.; Ellis, M. E.; Johnson, H. L. J. Med. Chem. 1980, 23, 1392.
15. Gaussian 94, Revision C.2: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
16. Krishnan, R.; Frisch, M. J.; Pople, J. A. J. Chem. Phys. 1980, 72, 4244.
17. (a) Møller, C.; Plesset, M. Phys. Rev. 1934, 46, 618.
18. (b) Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. 1976, 10, 1.
19. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
20. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
21. (a) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776.
22. (b) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 523.
23. (c) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 1645.
24. (d) Shang, H. S.; Head-Gordon, T. J. Am. Chem. Soc. 1994, 116, 1528.
25. (e) Navas, J. J.; Aleman, C.; Munoz-Guerra, S. J. Org. Chem. 1996, 61, 6849.
26. (f) Leon, S.; Martinez de Ilarduya, A.; Aleman, C.; Garcia-Alverez, M.; Munoz-Guerra, S. J. Phys. Chem. 1997, 101, 4208.
27. (a) Juaristi, E.; Labastida, V.; Antunez, S. J. Org. Chem. 1991, 56, 4802.
28. (b) Antunez, S.; Juaristi, E. J. Org. Chem. 1996, 61, 6465.
29. (c) Nunez, R.; Unwalla, R. J.; Cartledge, F. K.; Cho, S. G.; Riches, B. H.; Clenn, M. P.; Hungerford, N. L.; Lambert, L. K.; Brecknell, D. J.; Kitching, W. J. Chem. Soc., Perkin Trans. 2 1997, 1365.