A theoretical comparison of the chemical shifts of three related heterocycles: 1H-pyrazoles, 1H-1,2,4-triazoles and 1H-1,2,4-diazaphospholes

Journal of Molecular Structure: THEOCHEM

Volumn 942, Issue 1-3, 2010, Pages 1-6

  Alkorta, Ibon ^a   Blanco, Fernando ^a   Elguero, José ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

1,2,4 Diazaphospholes; B3LYP; GIAO; NMR; Pyrazoles; Triazoles

Indexed keywords

EID: 75149166575     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.11.024     Document Type: Article

References (36)

1. Elguero J., Marzin C., Linda P., and Katritzky A.R. The Tautomerism of Heterocycles (1976), Academic Press, New York
2. Minkin V.I., Garnovskii A.D., Elguero J., Katritzky A.R., and Denisko O.V. Adv. Heterocycl. Chem. 76 (2000) 157
3. Elguero J., Jacquier R., and Tien Duc H.C.N. Bull. Soc. Chim. Fr. (1966) 3727
4. Begtrup M., Boyer G., Cabildo P., Cativiela C., Claramunt R.M., Elguero J., Garcia J.I., Toiron C., and Vedsø P. Magn. Reson. Chem. 31 (1993) 107
5. Claramunt R.M., Sanz D., López C., Jiménez J.A., Jimeno M.L., Elguero J., and Fruchier A. Magn. Reson. Chem. 35 (1997) 35
6. Schmidpeter A., and Willhalm A. Angew. Chem. Int. Ed. 23 (1984) 903
7. Pi C., Elguero J., Wan L., Alkorta I., Zheng W., Weng L., Chen Z., and Wu L. Chem. Eur. J. 15 (2009) 6581
8. Schmidpeter A., and Wrackmeyer B. Z. Naturforsch. Teil B 41 (1986) 553
9. Rösch W., and Regitz M. Angew. Chem. Int. Ed. 23 (1984) 900
10. Abboud J.L.M., Cabildo P., Cañada T., Catalán J., Claramunt R.M., de Paz J.L.G., Elguero J., Homan H., Toiron C., and Yranzo G.I. J. Org. Chem. 57 (1992) 3938
11. Claramunt R.M., López C., Schmidpeter A., Willhalm A., Elguero J., and Alkorta I. Spectrosc. Int. J. 15 (2003) 27
12. Carrillo J.R., Cossío F.P., Díaz-Ortíz A., Gómez-Escalonilla M.J., De la Hoz A., Lecea B., Moreno A., and Prieto P. Tetrahedron 57 (2001) 4179
13. Märkl G., and Trötsch I. Angew. Chem. Int. Ed. 23 (1984) 901
14. Pavlik J.W., and Kebede N. J. Org. Chem. 62 (1997) 8325
15. A. Willhalm, Dissertation, University of Munich, Germany, 1987.
16. Tensmeyer L.G., and Ainsworth C. J. Org. Chem. 31 (1966) 1878
17. Fliege W., Grashey R., and Huisgen R. Chem. Ber. 117 (1984) 1194
18. Chai L., Zhao Y., Sheng Q., and Liu Z.Q. Tetrahedron Lett. 47 (2006) 9283
19. Albright J.D., and Goldman L. J. Org. Chem. 31 (1966) 273
20. Zheng W., Zhang G., and Fan K. Organmetallics 25 (2006) 1548
21. Silva A.M.S., Sousa R.M.S., Jimeno M.L., Blanco F., Alkorta I., and Elguero J. Magn. Reson. Chem. 46 (2008) 859
22. Blanco F., Alkorta I., and Elguero J. Magn. Reson. Chem. 45 (2007) 797
23. Berger S., Braun S., and Kalinowski H.O. NMR Spectroscopy of the Non-Metallic Elements (1997), John Wiley & Sons, Chichester p. 242
24. Klapötke T.M., Schulz A., White P.S., and Crawford M.J. Heteroatom. Chem. 9 (1998) 129
25. Patchkovskii S., and Ziegler T. J. Phys. Chem. A 106 (2002) 1088
26. Alkorta I., and Elguero J. Struct. Chem. 9 (1998) 187
27. van Wüllen C. Phys. Chem. Chem. Phys. 2 (2000) 2137
28. Becke A.D. Phys. Rev. A 38 (1988) 3098
29. Becke A.D. J. Chem. Phys. 98 (1993) 5648
30. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
31. Hariharan P.A., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
32. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724
33. Frisch M.J., Pople J.A., Krishnam R., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265
34. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., 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., Gonzalez C., and Pople J.A. Gaussian 03 (2003), Gaussian Inc., Pittsburgh, PA
35. Ditchfield R. Mol. Phys. 27 (1974) 789
36. London F. J. Phys. Radium 8 (1937) 397