The role of hyperconjugative π-aromaticity in the enhanced acidity of methyl-, silyl and germylcyclopentadienes

Molecular Physics

Volumn 108, Issue 19-20, 2010, Pages 2467-2476

  González Castrillo, Alberto ^a   Hurtado, Marcela ^a   Mó, Otilia ^a   Yáñez, Manuel ^a   Guillemin, Jean Claude ^b,c  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIV RENNES   (France)

^c Universitacute Europacute enne de Bretagne   (France)

Author keywords

cyclopentadienyl derivatives; density functional theory calculations; hyperconjugative aromaticity; intrinsic acidity

Indexed keywords

ACTIVATION BARRIERS; AROMATICITIES; CARBON ATOMS; CYCLOPENTADIENES; CYCLOPENTADIENYL DERIVATIVES; CYCLOPENTADIENYLS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DEPROTONATION PROCESS; ENHANCED ACIDITY; FIVE-MEMBERED RINGS; GASPHASE; GLOBAL MINIMA; HYPERCONJUGATION EFFECTS; INTRINSIC ACIDITY; METHYL DERIVATIVES; METHYLCYCLOPENTADIENE; PARENT COMPOUNDS; RELATIVE STABILITIES; SUBSTITUTED COMPOUNDS;

ACIDITY; ACIDS; AROMATIZATION; GASES; GERMANIUM; ISOMERS; OLEFINS; QUANTUM THEORY; SILICON; UNSATURATED COMPOUNDS;

DENSITY FUNCTIONAL THEORY;

EID: 78449286809     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268976.2010.502138     Document Type: Conference Paper

References (50)

1. E. C. Steiner and J. M. Gilbert, J. Am. Chem. Soc. 85, 3054(1963).
2. A. Streitwieser Jr and L. L. Nebenzahi, J. Am. Chem. Soc. 98, 2188(1976).
3. S. El Chaouch, J.-C. Guillemin, T. Karpati, T. Veszprémi, Organometallics, 20, 5405(2001).
4. M. Hurtado, O. Mó, M. Yáñez and J.-C. Guillemin, Croat. Chim. Acta 82, 1(2009).
5. J.-F. Gal; M. Decouzon; P.-C. Maria; A. I. González; O. Mó; M. Yáñez; S. El Chaouch and J.-C. Guillemin, J. Am. Chem. Soc. 123, 6353(2001).
6. R. Vianello, J. F. Liebman and Z. B. Maksic, Chem. Eur. J. 10, 5751(2004).
7. M. Hurtado, M. Yáñez and J. C. Guillemin, Phys. Chem. Chem. Phys. 11, 8759(2009).
8. M. Hurtado, A. M. Lamsabhi, O. Mó, M. Yáñez and J. C. Guillemin, Dalton Trans. 39, 4593(2010).
9. L. Nyulaszi and P. V. Schleyer, J. Am. Chem. Soc. 121, 6872(1999).
10. A. Bonny and S. R. Stobart, J. Chem. Soc.-Dalton Trans. 224(1980).
11. A. D. Becke, J. Chem. Phys. 98, 1372(1993).
12. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B 37, 785(1988).
13. A. M. Mebel, K. Morokuma and M. C. Lin, J. Chem. Phys. 103, 7414(1995).
14. A. Ricca and C. W. Bauschlicher Jr, Chem. Phys. Lett. 245, 150(1995).
15. A. L. Llamas-Saiz, C. Foces-Foces, O. Mó, M. Yáñez, E. Elguero and J. Elguero, J. Comput. Chem. 16, 263(1995).
16. A. I. González, O. Mó, M. Yáñez, E. Leon, J. Tortajada, J. P. Morizur, I. Leito, P. C. Maria and J. F. Gal, J. Phys. Chem. 100, 10490(1996).
17. M. Lamsabhi, M. Alcamí, O. Mó, W. Bouab, M. Esseffar, J. L. M. Abboud and M. Yáñez, J. Phys. Chem. A 104, 5122(2000).
18. P. Burk, I. A. Köppel, I. Köppel, R. Kurg, J.-F. Gal, P.-C. Maria, M. Herreros, R. Notario, J.-L. M. Abboud, F. Anvia and R. W. Taft, J. Phys. Chem. A 104, 2824(2000).
19. V. Raab, E. Gauchenova, A. Merkoulov, K. Harms, J. Sundermeyer, B. Kovacevic and Z. B. Maksic, J. Am. Chem. Soc. 127, 15738(2005).
20. B. Kovacevic and Z. B. Maksic, Chem. Commun. 1524(2006).
21. Z. B. Maksic and R. Vianello, Pure Appl. Chem. 79, 1003(2007).
22. I. Despotovic, Z. B. Maksic and R. Vianello, New J. Chem. 31, 52(2007).
23. G. Bouchoux, S. Desaphy, S. Bourcier, C. Malosse and R. N. B. Bimbong, J. Phys. Chem. B 112, 3410(2008).
24. S. Desaphy, C. Malosse and G. Bouchoux, J. Mass Spectrom. 43, 116(2008).
25. L. A. Curtiss, P. C. Redfern, K. Raghavachari and J. A. Pople, J. Chem. Phys. 114, 108(2001).
26. T. M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70(1993).
27. P. V. R. Schleyer, C. Maerker, A. Dransfeld, H. J. Jiao and N. Hommes, J. Am. Chem. Soc. 118, 6317(1996).
28. P. V. R. Schleyer, M. Manoharan, Z. X. Wang, B. Kiran, H. J. Jiao, R. Puchta and N. Hommes, Org. Lett. 3, 2465(2001).
29. Z. F. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta and P. V. Schleyer, Chem. Rev. 105, 3842(2005).
30. F. Feixas, E. Matito, J. Poater and M. Solà, J. Comput. Chem. 29, 1543(2008).
31. R. F. W. Bader, Atoms in Molecules. A Quantum Theory (Clarendon Press, Oxford, 1990).
32. C. F. Matta and R. J. Boyd, The Quantum Theory of Atoms in Molecules (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007).
33. A. D. Becke and K. E. Edgecombe, J. Chem. Phys. 92, 5397(1990).
34. B. Silvi and A. Savin, Nature 371, 683(1994).
35. A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev. 88, 899(1988).
36. S. Noury, X. Krokidis, F. Fuster and B. Silvi, Comput. Chem. 23, 597(1999).
37. K. B. Wiberg, R. F. W. Bader and C. D. H. Lau, J. Am. Chem. Soc. 109, 985(1987).
38. E. D. Glendening; J. K. Badenhoop; A. E. Reed; J. E. Carpenter; J. A. Bohmann; C. M. Morales and F. Weinhold In; http://www.chem.wisc.edu/~nbo5 ed.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI 2004.
39. C. C. Pye, J. D. Xidos, D. J. Burnell and R. A. Poirier, Can. J. Chem. 81, 14(2003).
40. J. E. Bentham, D. W. H. Rankin, E. A. Ebsworth and H. Moretto, Angew. Chem.-Int. Edit. Engl. 11, 640(1972).
41. M. J. Barrow, E. A. V. Ebsworth, M. M. Harding and D. W. H. Rankin, J. Chem. Soc.-Dalton Trans. 603(1980).
42. V. A. Mironov, A. N. Elizarova and E. V. Sobolev, Tetrahedron 19, 1939(1963).
43. S. M. Csicsery, J. Org. Chem. 25, 518(1960).
44. S. McLean and P. Haynes, Tetrahedron Lett. 2385(1964).
45. S. McLean, C. J. Webster and R. J. D. Rutherford, Can. J. Chem. 47, 1555(1969).
46. J. W. De Haan and H. Klooster., Rec. Trav. Chim. Pays-Bas 87, 298(1968).
47. S. Cradock, R. H. Findlay and M. H. Palmer, J. Chem. Soc.-Dalton Trans. 1650(1974).
48. J. A. Gámez, J. C. Guillemin, O. Mo and M. Yáñez, Chem. Eur. J 14, 2201(2008).
49. A. Eizaguirre, O. Mó, M. Yáñez and J. C. Guillemin, Chem. Eur. J 14, 10423(2008).
50. Z. B. Maksic and R. Vianello, J. Phys. Chem. A 106, 419(2002).