Structure of pyridynes and pyridyne N-oxides and their cycloaddition to ketene dialkyl acetals

Journal of Molecular Structure: THEOCHEM

Volumn 679, Issue 1-2, 2004, Pages 53-58

  Mariet, Natacha ^a   Ibrahim Ouali, Malika ^a   Parrain, Jean Luc ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Cycloaddition; Density functional calculations; Pyridyne formation energy; Pyridynes

Indexed keywords

ACETAL DERIVATIVE; KETENE DERIVATIVE; OXIDE; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 2542437992     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2004.04.002     Document Type: Article

References (47)

1. Pellissier H., Santelli M. Tetrahedron. 59:2003;701-730
2. Michellys P.-Y., Maurin P., Toupet L., Pellissier H., Santelli M. J. Org. Chem. 66:2001;115-122
3. Maurin P., Ibrahim-Ouali M., Santelli M. Eur. J. Org. Chem. 2002;151-156
4. Fleet G.W.J., Fleming I. J. Chem. Soc. C. 1969;1758-1763
5. May C., Moody C.J. Tetrahedron Lett. 26:1985;2123-2124
6. Furukawa N., Shibutani T., Fujihara H. Tetrahedron Lett. 28:1987;2727-2730
7. Khanapure S.P., Biehl E.R. Heterocycles. 27:1988;2643-2650
8. May C., Moody C.J. J. Chem. Soc. Perkin Trans. 1:1988;247-250
9. Reinecke M.G., Brown E.S., Capehart B.P., Minter D.E., Freeman R.K. Tetrahedron. 44:1988;5675-5680
10. Modi S.P., Archer S. J. Org. Chem. 54:1989;5189-5190
11. Kurita J., Kakusawa N., Yasuike S., Tsuchiya T. Heterocycles. 31:1990;1937-1940
12. Matsumoto K., Uchida T., Toda M., Aoyama K., Kakehi A., Shigihara A., Lown J.W. Tetrahedron Lett. 33:1992;7643-7646
13. Tsukazaki M., Snieckus V. Heterocycles. 33:1992;533-536
14. Gribble G.W., Saulnier M.G. Heterocycles. 35:1993;151-169
15. Walters M.A., Shay J.J. Tetrahedron Lett. 36:1995;7575-7578
16. Walters M.A., Shay J.J. Synth. Commun. 27:1997;3573-3579
17. Connon S.J., Hegarty A.F. J. Chem. Soc., Perkin Trans. 1:2000;1245-1249
18. Diaz M., Cobas A., Guitián E., Castedo L. Eur. J. Org. Chem. 2001;4543-4549
19. Connon S.J., Hegarty A.F. Tetrahedron Lett. 42:2001;735-737
20. Hart H. Arynes and Hetarynes. Patai S. The Chemistry of Functional Groups. Suppl. C2: The Chemistry of Triple Bonded Functional Groups. 1994;1017-1134 Wiley, Chichester
21. Reinecke M.G. Tetrahedron. 38:1982;427-498
22. Maurin P., Ibrahim-Ouali M., Parrain J.-L., Santelli M. J. Mol. Struct. (Theochem). 637:2003;91-100
23. Mariet N., Ibrahim-Ouali M., Santelli M. Tetrahedron Lett. 43:2002;5789-5791
24. Nam H.-H., Leroi G.E. J. Am. Chem. Soc. 110:1988;4096-4097
25. Nam H.H., Leroi G.E. Tetrahedron Lett. 31:1990;4837-4840
26. Kramer J., Berry R.S. J. Am. Chem. Soc. 94:1972;8336-8347
27. Adam W., Grimison A., Hoffmann R. J. Am. Chem. Soc. 91:1969;2590-2599
28. Radom L., Nobes R.H., Underwood D.J., Li W.-K. Li. Pure Appl. Chem. 58:1986;75-88
29. Nam H.H., Leroi G.E., Harrison J.F. J. Phys. Chem. 95:1991;6514-6519
30. Cramer C.J., Debbert S. Chem. Phys. Lett. 287:1998;320-326
31. Liu R., Tate D.R., Clark J.A., Moody P.R., Van Buren A.S., Krauser J.A. J. Phys. Chem. 100:1996;3430-3434
32. Becke A.D. J. Chem. Phys. 98:1993;5648-5652
33. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785-789
34. Foresman J.B., Frisch A.E. Exploring Chemistry with Electronic Structure Methods. second ed. 1996;Gaussian Inc, Pittsburgh
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., 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, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, 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, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
36. Bauschlicher C.W. Jr., Partridge H. J. Chem. Phys. 103:1995;1788-1791
37. Jiao H., Schleyer P.R., Beno B.R., Houk K.N., Warmuth R. Angew. Chem. Int. Ed. Engl. 37:1997;2761-2764
38. Orendt A.M., Facelli J.C., Radziszewski J.G., Horton W.J., Grant D.M., Michl J. J. Am. Chem. Soc. 118:1996;846-852
39. Mata F., Quintana M.J., Sorensen G.O. Pyridine. J. Mol. Struct. 42:1977;1-5
40. See also Pyckhout W., Horemans N., Van Alsenoy C., Geise H.J., Rankin D.W.H. J. Mol. Struct. 156:1987;315-329
41. Sorensen G.O., Tang-Pedersen Å., Pedersen E.J. Pyridine N-oxide. J. Mol. Struct. 101:1983;263-268
42. The reaction of 3-chloro-2-picoline N-oxide with potassium amide to give 3- or 4-amino-2-picoline 1-oxyde seems to involve the formation of 3, 4-pyridyne N-oxide, see: Kato T., Niitsuma T. Heterocycles. 1:1973;233-236
43. The simplest case, a 1, 4-diradical C(a)-C2-C(b) can be obtain from a hydrocarbon by the homolytic cleavage of two CH bonds. Two pathways occurs C(a)H-C2-C(b)H→(C(a)-C2-C(b)H→(C(a)-C2-C(b) or C(a)H-C2-C(b) H→(C(a)H-C2-C(b)→(C(a)-C2-C(b). We assume that the thermodynamic stability of the diradical is not affected by the pathway followed for its generation (the presence of one radical center does not affect the enthalpy for creation of the second radical center). For a discussion, see: Zhang D.Y., Borden W.T. J. Org. Chem. 67:2002;3989-3995
44. Hrovat D.A., Borden W.T. J. Am. Chem. Soc. 123:2001;4069-4072
45. Hrovat D.A., Beno B.R., Lange H., Yoo H.-Y., Houk K.N., Borden W.T. J. Am. Chem. Soc. 121:1999;10529-10537
46. Calculated at the Becke3LYP/6-311G(d, p) level (energy in hartrees), 3-methylpyridin-4-yl radical: total energy, -286.99267, ZPE (scaled by a factor of 0.989 [18]), 0.10155; 4-methylpyridin-3-yl radical: total energy, -286.99161, ZPE (scaled by a factor of 0.989 [18]), 0.10275.
47. Hammond G.S. J. Am. Chem. Soc. 77:1955;334-338