Experimental intrinsic barriers to amide-amide interaction. Transannular cyclolization in a cyclic diamide

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 2, 2002, Pages 244-246

  Tineo, Evis ^a   Pekerar, Sarah V ^b   Núñez, Oswaldo ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

^b INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CATALYSIS; DISSOLUTION; PHASE EQUILIBRIA; PHASE TRANSITIONS; PROTONS;

AMIDE AMIDE INTERACTION; CYCLIC DIAMIDE; TRANSANNULAR CYCLOLIZATION;

AMINES;

EID: 0036007678     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b109000c     Document Type: Article

References (15)

1. O. Núñez, J. Rodríguez, L. Angulo J. Phys. Org. Chem. 1994 7 80.
2. L. Angulo, O. Núñez J. Chem. Res. (S) 1996 214–215.
3. L. Angulo, O. Núñez J. Chem. Res. (M) 1996 1123.
4. G. I. Golver, R. B. Smith, H. Rapoport J. Am. Chem. Soc. 1965 87 2003.
5. R. G. Griot, A. J. Frey Tetrahedron 1963 19 1661.
6. J. P. Guthrie Acc. Chem. Res. 1983 16 122.
7. S. S. Shaik, H. B. Schlegel and S. Wolfe Theoretical Aspects of Physical Organic Chemistry. The SN2 Mechanism, John Wiley and Sons, Inc., New York, 1992.
8. M. Rothe, I. Rothe, T. Toth and K.-D. Steffen Aminoacyl Incorporation in Lactams and Cyclic Peptides. Peptides, North-Holland Publishing Company, Amsterdam, 1967.
9. H. D. Law The Organic Chemistry of Peptides, Wiley-Interscience, London, 1970 138.
10. A difference of 0.5 ppm (induced by anisotropic effects) in the geminal protons attached to a carbonyl group is observed in the structure of camphor:.
11. HyperChem for Windows. Molecular Mechanics. Method MM+.
12. B. M. Fung, P. M. Olympia Mol. Phys. 1970 19 685.
13. S. A. Smith, T. O. Levante, B. H. Meier, R. R. Ernst J. Magn. Reson. 1994 106a 75.
14. P. K. Glasoe, F. A. Long J. Phys. Chem. 1960 64 188.
15. T. Winkler, T. Leutert Helv. Chim. Acta 1982 65 1760.