Can conventional bases and unsaturated hydrocarbons be converted into gas-phase superacids that are stronger than most of the known oxyacids? the role of beryllium bonds

Chemistry - A European Journal

Volumn 19, Issue 35, 2013, Pages 11637-11643

  Yáñez, Manuel ^a   Mõ, Otilia ^a   Alkorta, Ibon ^b   Elguero, José ^b  

^a CSIC   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

acidity; azoles; basicity; beryllium; superacidic systems

Indexed keywords

AB INITIO CALCULATIONS; AZOLES; CARBONYL GROUPS; DEPROTONATED SPECIES; ELECTRON DONORS; NEUTRAL SPECIES; PERCHLORIC ACIDS; UNSATURATED HYDROCARBONS;

ACIDITY; ACIDS; ALKALINITY; BERYLLIUM; ETHYLENE; GASES; SULFURIC ACID;

AROMATIC HYDROCARBONS;

ACID; BERYLLIUM; HYDROCARBON; PYRROLE DERIVATIVE;

ACIDITY; ARTICLE; BASICITY; CHEMICAL STRUCTURE; CHEMISTRY; SUPERACIDIC SYSTEMS;

ACIDITY; AZOLES; BASICITY; BERYLLIUM; SUPERACIDIC SYSTEMS;

ACIDS; AZOLES; BERYLLIUM; HYDROCARBONS; MODELS, MOLECULAR;

EID: 84882879289     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300808     Document Type: Article

References (50)

1. G. C. Pimentel, A. L. McClelland, The Hydrogen Bond, W. H. Freeman and Co., San Francisco, 1960
2. Hydrogen Bonding-New Insights (Ed.:, S. J. Grabowski,), Springer, Dordrecht, 2006.
3. P. Metrangolo, G. Resnati, Chem. Eur. J. 2001, 7, 2511-2519
4. T. Clark, M. Hennemann, J. S. Murray, P. Politzer, J. Mol. Model. 2007, 13, 291-296
5. P. Politzer, P. Lane, M. C. Concha, Y. Ma, J. S. Murray, J. Mol. Model. 2007, 13, 305-311.
6. V. I. Bakhmutov, Dihydrogen Bonds: Principles, Experiments, and Applications, John Wiley & Sons, Hoboken, 2008.
7. Gas Phase Ion Chemistry (Ed.:, M. T. Bowers,), Academic Press, New York, 1979
8. Advances in Gas-Phase Ion Chemistry (Eds.:, N. G. Adams, L. M. Babcock,), Jai Press Ltd., Hampton Hill, 1996.
9. O. Hassel, Science 1970, 170, 497-502.
10. J. A. Kroll, D. D. Shillady, J. Am. Chem. Soc. 1973, 95, 1422-1425
11. A. A. Fiorillo, J. M. Galbraith, J. Phys. Chem. A 2004, 108, 5126-5130
12. J. A. Plumley, J. D. Evanseck, J. Phys. Chem. A 2007, 111, 13472-13483.
13. A. Haaland, Angew. Chem. 1989, 101, 1017-1032
14. Angew. Chem. Int. Ed. Eng. 1989, 28, 992-1007
15. J. Bauer, H. Braunschweig, R. D. Dewhurst, Chem. Rev. 2012, 112, 4329-4346.
16. E. Sheepwash, V. Krampl, R. Scopelliti, O. Sereda, A. Neels, K. Severin, Angew. Chem. 2011, 123, 3090-3093
17. Angew. Chem. Int. Ed. 2011, 50, 3034-3037.
18. M. A. Dvorak, R. S. Ford, R. D. Suenram, F. J. Lovas, K. R. Leopold, J. Am. Chem. Soc. 1992, 114, 108-115.
19. D. P. Zhong, A. H. Zewail, Proc. Natl. Acad. Sci. USA 1999, 96, 2602-2607.
20. M. Yáñez, P. Sanz, O. Mõ, I. Alkorta, J. Elguero, J. Chem. Theory Comput. 2009, 5, 2763-2771.
21. M. A. Lee, N. W. Winter, W. H. Casey, J. Phys. Chem. 1994, 98, 8641-8647.
22. O. Mõ, M. Yáñez, I. Alkorta, J. Elguero, J. Chem. Theory Comput. 2012, 8, 2293-2300.
23. I. Alkorta, J. Elguero, J. E. Del Bene, O. Mo, M. Yanez, Chem. Eur. J. 2010, 16, 11897-11905.
24. J. H. Ren, C. J. Cramer, R. R. Squires, J. Am. Chem. Soc. 1999, 121, 2633-2634.
25. M. Hurtado, M. Yáñez, R. Herrero, A. Guerrero, J. Z. Dávalos, J.-L. M. Abboud, B. Khater, J. C. Guillemin, Chem. Eur. J. 2009, 15, 4622-4629.
26. A. Martín-Sõmer, A. Lamsabhi, M. Yanez, J. Z. Davalos, J. Gonzalez, R. Ramos, J. C. Guillemin, Chem. Eur. J. 2012, 18, 15699-15705.
27. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications, Wiley-VCH, Weinheim, 2003
28. J. A. Joule, K. Mills, Heterocyclic Chemistry, Wiley-Blackwell, Chichester, 2010
29. H. Gao, J. n. M. Shreeve, Chem. Rev. 2011, 111, 7377-7436.
30. A. P. Sadimenko, Adv. Heterocycl. Chem. 2001, 80, 157-240
31. A. P. Sadimenko, Adv. Heterocycl. Chem. 2002, 83, 117-187
32. A. P. Sadimenko, Adv. Heterocycl. Chem. 2003, 84, 191-217
33. A. P. Sadimenko, Adv. Heterocycl. Chem. 2010, 100, 175-194.
34. D. S. Robertson, Clin. Biochem. 2011, 44, 1363-1369
35. M. A. Iradyan, N. S. Iradyan, G. M. Stepanyan, F. G. Arsenyan, B. T. Garibdzhanyan, Pharm. Chem. J. 2010, 44, 175-182.
36. M. P. Dressel, S. Nogai, R. J. F. Berger, H. Schmidbaur, Z. Naturforsch. 2003, 58b, 173-182.
37. L. A. Curtiss, P. C. Redfern, K. Raghavachari, J. Chem. Phys. 2007, 126, 084108.
38. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
39. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon Press, Oxford, 1990
40. The Quantum Theory of Atoms in Molecules (Eds.:, C. F. Matta, R. J. Boyd,), Wiley-VCH, Weinheim, 2007.
41. A. J. Gianola, T. Ichino, R. L. Hoenigman, S. B. Kato, W. C. Lineberger, J. Phys. Chem. A 2005, 109, 11504-11514.
42. A. J. Gianola, T. Ichino, S. Kato, V. M. Bierbaum, W. C. Lineberger, J. Phys. Chem. A 2006, 110, 8457-8466.
43. J. Catalan, R. M. Claramunt, J. Elguero, M. Menedez, F. Anvia, J. H. Quian, M. Taagepera, R. W. Taft, J. Am. Chem. Soc. 1988, 110, 4105-4111.
44. NIST Chemistry Webbook, NIST Standard Reference Database Number 69 (Eds.: P. J. Linstrom, W. G. Mallard), release June 2005, National Institute of Standards and Technology, Gaithersburg, MD, 20899, http://webbook.nst.gov, 2012.
45. K. B. Wiberg, R. F. W. Bader, C. D. H. Lau, J. Am. Chem. Soc. 1987, 109, 985-1001.
46. A. Corma, Chem. Rev. 1995, 95, 559-614
47. J. Sommer, M. Hachoumy, F. Garin, D. Barthomeuf, J. Am. Chem. Soc. 1994, 116, 5491-5492
48. J. F. Haw, Phys. Chem. Chem. Phys. 2002, 4, 5431-5441.
49. A. Kütt, T. Rodima, J. Saame, E. Raamat, V. Maemets, I. Kaljurand, I. A. Koppel, R. Y. Garlyauskayte, Y. L. Yagupolskii, L. M. Yagupolskii, E. Bernhardt, H. Willner, I. Leito, J. Org. Chem. 2011, 76, 391-395.
50. Z. B. Maksic̈, B. Kovacevic, R. Vianello, Chem. Rev. 2012, 112, 5240-5270.