Proton transfer in C-halogen pyrazole cyclamers. A theoretical study

Structural Chemistry

Volumn 19, Issue 2, 2008, Pages 191-198

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

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

DFT; Proton transfer; Pyrazole; Tautomerism

Indexed keywords

EID: 46249113822     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-007-9271-x     Document Type: Article

References (37)

1. Cammers A, Parkin S (2004) Cryst Eng Commun 6:168
2. Etter MC, Parker DL, Ruberu SR, Panunto TW, Britton DJ (1990) J Incl Phenom Macrocycl Chem 8:395
3. (a) Etter MC (1990) Acc Chem Res 23:120;
4. (b) Etter MC, MacDonald J, Bernstein J (1990) Acta Crystallogr B46:256
5. (a) Bernstein J, Etter MC, Leiserowitz L (1994) The role of hydrogen bonding in molecular assemblies. In: Dunitz JD, Burgi HB (eds) Structure correlations, Vol 2. VCH, Weinheim, pp 431-507;
6. (b) Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555
7. López C, Claramunt RM, García MA, Pinilla E, Torres MR, Alkorta I, Elguero J (2007) Cryst Growth Des 7:1176
8. Haghiri A, Lerner HW, Wagner M, Bats JW 2002 Acta Crystallogr E58:o1378
9. CSD ver. 5.28 (updated January & May 2007): Allen FH (2002) Acta Crystallogr B58:380;
10. Allen FH, Motherwell WDS (2002) Acta Crystallogr B58:407
11. (a) Becke AD (1988) Phys Rev A 38:3098;
12. (b) Becke AD (1993) J Chem Phys 98:5648;
13. (c) Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785
14. (a) Hehre WJ, Ditchfield R, Pople JA (1972) J Chem Phys 56:2257;
15. (b) Clark T, Chandrasekar J, Schleyer PvR (1983) J Comput Chem 4:294
16. Gaussian 03, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Adao C, Jaramill, J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian, Inc., Pittsburgh PA, 2003
17. Bader RFW (1990) Atoms in molecules: a quantum theory. Clarendon Press, Oxford;
18. Biegler-König FW, Bader RFW, Tang TH (1982) J Comput Chem 3:317
19. Klein O, Aguilar-Parrilla F, López JM, Jagerovic N, Elguero J, Limbach HH (2004) J Am Chem Soc 126:11718
20. (a) Elguero J, Marzin C, Katritzky AR, Linda P (1976) The tautomerism of heterocycles. Academic Press, New York, p 655;
21. (b) Minkin VI, Garnosvskii AD, Elguero J, Katritzky AR, Denisko OV (2000) Adv Heterocycl Chem 76:157
22. Huheey JE (1983) Inorganic chemistry. Harper & Row, New York
23. Foces-Foces C, Alkorta I, Elguero J (2000) Acta Crystallogr Sect B 56:1018
24. Alkorta I, Elguero J, Foces-Foces C, Infantes L (2006) Arkivoc ii:15
25. (a) Kubinyi H (1995) In: Wolff ME (ed) Burger's medicinal chemistry and drug discovery, Vol 1. Wiley, New York, p 497;
26. (b) Selassie CD (2003) In: Abraham DJ (ed) Burger's medicinal chemistry and drug discovery, Vol 1. Wiley, Hoboken, pp 19-23
27. Paz JLG, Elguero J, Foces-Foces C, Llamas-Saiz AL, Aguilar-Parrilla F, Klein O, Limbach HH (1997) J Chem Soc Perkin Trans 2:101
28. Pauling L (1947) J Am Chem Soc 69:542
29. Brown ID (1992) Acta Crystallogr B 48:553
30. Ramos M, Alkorta I, Elguero J, Golubev NS, Denisov GS, Benedict H, Limbach HH (1997) J Phys Chem A 101:9791
31. Alkorta I, Elguero J (1999) Struct Chem 10:157
32. Alkorta I, Picazo O, Elguero J (2004) Tetrahedron-Asymmetry 15:1391
33. Picazo O, Alkorta I, Elguero J (2003) J Org Chem 68:7485
34. Sánchez M, Provasi PF, Aucar GA, Alkorta I, Elguero J (2005) J Phys Chem B 109:18189
35. Espinosa E, Alkorta I, Elguero J, Molins E (2002) J Chem Phys 117:5529
36. Stride JA, Jayasooriya UA, Zanotti JM, Kahn R (2006) New J Chem 30:425
37. Castaneda JP, Denisov GS, Kucherov SYu, Schreiber VM, Shurukhina AV (2003) J Mol Struct 660:25