Feasibility of the spontaneous gas-phase proton transfer equilibria between neutral Brønsted acids and Brønsted bases

Journal of Physical Organic Chemistry

Volumn 21, Issue 7-8, 2008, Pages 571-574

  Burk, Peeter ^a   Koppel, Ivar ^a   Trummal, Aleksander ^b   Koppel, Ilmar A ^a  

^a UNIVERSITY OF TARTU   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

Gas phase acidity; Gas phase basicity; Spontaneous proton transfer in the gas phase

Indexed keywords

ACIDS; FLOW INTERACTIONS; PHASE EQUILIBRIA; PROTONS;

ACID BASE; COMPUTATIONAL INVESTIGATIONS; GAS PHASE; TRANSFER EQUILIBRIUM;

PROTON TRANSFER;

EID: 46949092915     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1322     Document Type: Conference Paper

References (35)

1. J. Bartmess, in NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (Eds: P. Linstrom, W. Mallard ) National Institute of Standards and Technology, Gaithersburg MD, 20899, 2005. (http://webbook.nist.gov)
2. I. A. Koppel, R. W. Taft, F. Anvia, S.-Z. Zhu, L.-Q. Hu, K.-S. Sung, D. D. DesMarteau, L. M. Yagupolskii, Y. L. Yagupolskii, N. V Ignat'ev, N. V. Kondratenko, A. Y. Volkonskii, V. M. Vlassov, R. Notario, P.-C. Maria, J. Am. Chem. Soc. 1994, 116, 3047.
3. I. A. Koppel, P. Burk, I. Koppel, I. Leito, T. Sonoda, M. Mishima, J. Am. Chem. Soc. 2000, 122, 5114.
4. I. A. Koppel, P. Burk, I. Koppel, I. Leito, J. Am. Chem. Soc. 2002, 124, 5594.
5. Z. B. Maksic, R. Vianello, Pure Appl. Chem. 2007, 79, 1003.
6. I. Krossing, I. Raabe, Angew. Chem. Int. Ed. 2004, 43, 2066.
7. E. S. Stoyanov, K.-C. Kim, C A. Reed, J. Am. Chem. Soc. 2006, 128, 8500.
8. C. A. Reed, Chem. Comm. 2005, 1669.
9. E. Hunter, S. Lias, in NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (Eds: R Lindstrom, W. Mallard) National Institute of Standards and Technology, Gaithersburg MD, 20899, 2005. (http://webbook.nist.gov)
10. I. Kaljurand, I. A. Koppel, A. Kütt, E.-I. Rõõm, T. Rodima, I. Koppel, M. Mishima, I. Leito, J. Phys. Chem. A 2007, 111, 1245.
11. M. F. Butman, L. S. Kudin, K. S. Krasnov, Russ. J. Inorg. Chem. (Transi. Zh. Neorg. Khim.) 1984, 29, 2150.
12. P. Burk, I. A. Koppel, Int. J. Quant. Chem. 1994, 51, 313.
13. P. Burk, K. Sillar, I. A. Koppel, J. Mol. Struct. THEOCHEM 2001, 543, 223.
14. P. Burk, S. Tamp, J. Mol. Struct. THEOCHEM 2003, 638, 119.
15. V. Raab, E. Gauchenova, A. Merkoulov, K. Harms, J. Sundermeyer, B. Kovacevic, Z. B. Maksic, J. Am. Chem. Soc. 2005, 127, 15738.
16. B. Kovacevic, Z. B. Maksic, Chem. Comm. 2006, 1524.
17. I. A. Koppel, R. Schwesinger, T. Breuer, P. Burk, K. Herodes, I. Koppel, I. Leito, M. Mishima, J. Phys. Chem. A 2001, 105, 9575.
18. A. A. Kolomeitsev, I. A. Koppel, T. Rodima, J. Barten, E. Lork, G.-V. Röschenthaler, I. Kaljurand, A. Kütt, I. Koppel, V. Mäemets, I. Leito, J. Am. Chem. Soc. 2005, 127, 17656.
19. J. Catalan, J. Org. Chem. 1999, 64, 1908.
20. I. A. Koppel, F. Anvia, R. W. Taft, WATOC II, Toronto 1990, B1-O7.
21. I. Koppel, J. Chim. Phys. Phys. -Chim. Biol. 1992, 89, 1545.
22. J. Catalan, J. Palomar, Chem. Phys. Lett. 1998, 293, 511.
23. O. Mo, M. Yanez, L Gonzales, J. Elguero, ChemPhysChem 2001, 2, 465.
24. L. Benco, T. Demuth, J. Hafner, F. Hutschka, Chem. Phys. Lett. 2000, 330, 457.
25. S. Simons, M. Sodupe, J. Bertran, Theor. Chem. Acc. 2004, 111, 217.
26. I. Alkorta, I. Rozas, O. Mó, M. Yáñez, J. Elguero, J. Phys. Chem. A 2001, 105, 7481.
27. Y. D. Huh, R. J. Cross, M. Saunders, J. Am. Chem. Soc. 1990, 112, 3774.
28. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr. T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
29. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
30. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623.
31. C. Lee, E. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
32. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200.
33. R. Krishnan, J. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.
34. G. W. Spitznagel, T. Clark, J. Chandrasekhar, Pv. R. Schleyer, J. Comp. Chem. 1982, 3, 363.
35. P. Burk, I. A. Koppel, I. Koppel, I. Leito, O. Travnikova, Chem. Phys. Lett. 2000, 323, 482.