The effect of nitrogen atom on double bond pyramidalization

Journal of Chemical Crystallography

Volumn 34, Issue 7, 2004, Pages 477-481

  Özen, Recep ^a   Guven, Kutalmis ^b   Can, Hatice ^a   Balci, Metin ^c  

^a MERSIN UNIVERSITY   (Turkey)

^b KIRIKKALE UNIVERSITY   (Turkey)

^c MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

ab initio calculations; cycloaddition; double bond pyramidalization; Exocyclic diene; X ray analysis

Indexed keywords

2,3 DIMETHYLENEBICYCLO[2.2.1]HEPTANE; 4 PHENYL 1,2,4 TRIAZOLE 3,5 DIONE; 6 PHENYL 4,6,8 TRIAZATETRACYCLO[9.2.1.0 2,10 .0 4,8 ]TETRADEC 2(10) ENE 5,7 DIONE; HEPTANE DERIVATIVE; NITROGEN; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; GEOMETRY; X RAY ANALYSIS;

EID: 3242890761     PISSN: 10741542     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:JOCC.0000035390.96988.db     Document Type: Article

References (38)

1. Bordon, W.T. Chem. Rev. 1989, 89, 1095-1109.
2. Paquette, L.A. In Stereochemistry and Reactivity of Systems Containing π Electrons; Watson, W.H., Ed.; Verlag Chemie International: Deerfield Beach, Florida, 1983; pp. 41-73.
3. Bartlett, P.D.; Blakeney, A.J.; Combs, G.L.; Galloy, J.; Roof, A.A.M.; Subramanyam, R.; Watson, W.H.; Winter, W.J.; Wu, C. In Stereochemistry and Reactivity of Systems Containing π Electrons; Watson, W.H., Ed.; Verlag Chemie International: Deerfield Beach, Florida, 1983; pp. 75-104.
4. Gleiter, R.; Böhm, M.C.; Watson, W.H. (Ed.), Stereochemistry and Reactivity of Systems Containing π Electrons, Verlag Chemie International: Deerfield Beach, Florida, 1983; pp. 105-146.
5. (a) Saracoglu, N.; Balci, M. Helv. Chim. Acta 2001, 84, 707-714.
6. (b) Saracoglu, N.; Menzek, A.; Sayan, S.; Salzner, U.; Balci, M. J. Org. Chem. 1999, 64, 6670-6676.
7. (c) Menzek, A.; Balci, M.; Watson, W.H.; Krawiec, M. J. Org. Chem. 1995, 60, 829-832.
8. (d) Balci, M.; Bourne, S.A.; Menzek, A.; Saracoglu, N.; Watson, W.H. J. Chem. Crystallogr. 1995, 25, 107-116.
9. (e) Menzek, A.; Krawiec, M.; Watson, W.H.; Balci, M. J. Org. Chem. 1991, 56, 6755-6758.
10. (a) Watson, W.H.; Galloy, J.; Bartlett, P.D.; Roof, A.A.M. J. Am. Chem. Soc. 1981, 103, 2022-2031.
11. (b) Bartlett, P.D.; Blakeney, A.J.; Kimura, M.; Watson, W.H. J. Am. Chem. Soc. 1980, 102, 1383-1390.
12. (c) Paquette, L.A.; Carr, R.V.C.; Bohem, M.C.; Gleiter, R. J. Am. Chem. Soc. 1978, 100, 1186-1188.
13. (d) Gajhede, M.; Jorgensen, F. S.; Kopecky, K.R.; Watson, W.H.; Kashyap, R.P. J. Org. Chem. 1985, 50, 4395-4397.
14. (a) Antol, I.; Eckert-Maksic, M.; Margetic, D.; Maksic, Z. B.; Kowski, K.; Rademacher, P. Eur. J. Org. Chem. 1998, 1403-1408.
15. (b) Eckert-Maksic, M.; Margetic, D.; Maksic, Z. B.; Rademacher, P.; Kowski, K. Tetrahedron Lett. 1993, 43, 6951-6954.
16. Ermer, O.; Bell, P.; Mason, S. Angew. Chem. Int. Ed. Engl. 1989, 28, 1239-1240.
17. Houk, K.N. In Stereochemistry and Reactivity of Systems Containing π Electrons; Watson, W. H., Ed.; Verlag Chemie International: Deerfield Beach, Florida, 1983; pp. 1-40.
18. (a) Spanget-Largen, J.; Gleiter, R.; Tetrahedron Lett. 1982, 23, 2435-2438.
19. (b) Spanget-Largen, J.; Gleiter, R. Tetrahedron Lett. 1982, 23, 927-930.
20. Wagner, H.U.; Szeimies, G.; Chandrasekhar, J.; Schleyer. P.V.R.; Pople, J.A.; Binkley, J. S. J. Am. Chem. Soc. 1978, 100, 1210-1213.
21. (a) Holthousen, M.C.; Koch, W. J. Phys. Chem. 1993, 97, 10021-10028.
22. (b) William, R.V.; Edwards, W.D.; Gadgil, V.R.; Colvin M.E.; Seidl, E.T.; van der Helm, D.; Hosain, M.B. J. Org. Chem. 1998, 63, 5268-5271.
23. (c) William, R.V.; Colvin, M.E.; Tran, N.; Warrener, R. N.; Margetic, D. J. Org. Chem. 2000, 65, 562-567.
24. (a) Griesbeck, A.G.; Deufel, T.; Hohlneicher, G.; Rebentisch, R.; Steinwasser, J. Eur. J. Org. Chem. 1998, 1759-1762.
25. (b) Camps, P.; Font-Bardia, M.; Mendez, M.; Perez, F.; Pujol, X.; Solans, X.; Vasquez, S.; Vilalta, M. Tetrahedron, 1998, 54, 4679-4696.
26. (c) Williams, R.V.; Colvin, M.T.; Tran, N.; Warrener, R. N.; Margetic, D. J. Org. Chem. 2000, 65, 562-567.
27. (d) Margtic, D.; Williams, R. V.; Warrener, R. N. J. Org. Chem. 2003, 68, 9186-9190.
28. Can, H.; Zahn, D.; Balci, M.; Brickmann, J. Eur. J. Org. Chem. 2003, 1111-1117.
29. Todo, T.; Ohya, T.; Mukai, T. Bull. Chem. Soc. Jpn. 1972, 45, 1561-1562.
30. Carrupt, P.A.; Berchier F.; Vogel, P. Helv. Chim. Acta 1985, 68, 1716-1729.
31. PC Spartan Pro, Wavefunction, Inc.; Irvine, CA.
32. Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
33. Petersson G.A.; Al-Laham, M.A.; J. Chem. Phys. 1991, 94, 6081-6090.
34. Petersson, G.A.; Bennett, A.; Tensfeldt, T.G.; Al-Laham, M.A.; Shirley, W.A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193-2218.
35. Frisch, M.J.; Frisch, A.E.; Foresman, J.B.; Gaussian 94 User's Reference; Gaussian, Inc.: Pittsburgh, PA, 1994-1995.
36. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A.; Jr., Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavchari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Baboul, A.G.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Andres, J.L.; Gonzalez, C.; Head-Gordon, M.; Replogle E.S.; Pople, J.A Gaussian 98, Revision A.8; Gaussian, Inc.: Pittsburgh PA, 1998.
37. Altomare, A.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst. 1993, 26, 343-350.
38. Beurskens, P.T.; Admiraal, G.; Beurskens, G.; Bosman, W.P.; de Gelder, R.; Israel, R.; Smits, J.M.M. The DIRDIF-94 Program System, Technical Report of the Crystallograhy Laboratory; University of Nijmegen: The Netherlands, 1994.