Basicity of amines in the gas phase - Analysis of the base-strengthening effect of an N-trityl group by use of a triadic formula

European Journal of Organic Chemistry

Volumn , Issue 11, 2006, Pages 2581-2589

  Vianello, Robert ^a   Maskill, Howard ^b   Maksić, Zvonimir B ^a,c  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Ab initio MO calculation; Base strength; Proton affinity; Steric hindrance; Triadic formula; Tritylamine

Indexed keywords

EID: 33744951546     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500994     Document Type: Article

References (41)

1. a) J. F. W. McOmie, Protective Groups in Organic Chemistry, Plenum Press, London, New York, 1973;
2. b) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, 3rd edition, New York, 1999.
3. a) M. C. Lopez, J. C. Martinez, I. Demirtas, H. Maskill, E. Stix, Org. Reactivity 1997, 31, 71-77;
4. b) J. Crugeiras, H. Maskill, J. Chem. Soc., Perkin Trans. 2 1998, 1901-1907;
5. c) M. Canle, L. I. Demirtas, H. Maskill, J. Chem. Soc., Perkin Trans. 2 2001, 1748-1752.
6. a) E. M. Arnett, R. D. Bushick, J. Am. Chem. Soc. 1964, 86, 1564-1571;
7. b) H. Nicholson, P. A. H. Wyatt, J. Chem. Soc. B 1968, 198-202;
8. c) M. J. Postle, P. A. H. Wyatt, J. Chem. Soc., Perkin Trans. 2 1972, 474-479;
9. d) M. J. Cook, N. L. Dassanayake, C. D. Johnson, A. R. Katritzky, T. W. Toone, J. Am. Chem. Soc. 1975, 97, 760-764;
10. e) W. H. Lee, H. Maskill, J. Chem. Soc., Perkin Trans. 2 1994, 1463-1466;
11. f) J. Crugeiras, H. Maskill, Can. J. Chem. 1999, 77, 530-536;
12. g) J. Crugeiras, H. Maskill, J. Chem. Soc., Perkin Trans. 2 2000, 441-445.
13. a) N. C. Deno, J. J. Jaruzelski, A. Schriesheim, J. Am. Chem. Soc. 1955, 77, 3044-3051;
14. b) N. C. Deno, A. Schreisheim, J. Am. Chem. Soc. 1955, 77, 3051-3054;
15. c) N. C. Deno, H. E. Berkheimer, W. L. Evans, H. J. Peterson, J. Am. Chem. Soc. 1959, 81, 2344-2347;
16. d) E. M. Arnett, R. D. Bushick, J. Am. Chem. Soc. 1964, 86, 1564-1571;
17. e) M. J. Cook, N. L. Dassanayake, C. D. Johnson, A. R. Katritzky, T. W. Toone, J. Am. Chem. Soc. 1975, 97, 760-764;
18. f) R. A. Cox, K. Yates, Can. J. Chem. 1983, 67, 2225-2243.
19. M. Canle, L. W. Clegg, I. Demirtas, M. R. J. Elsegood, H. Maskill, J. Chem. Soc., Perkin Trans. 2 2000, 85-92.
20. L. M. Canle , W. Clegg, I. Demirtas, M. R. J. Elsegood, J. Haider, H. Maskill, P. C. Miatt, J. Chem. Soc., Perkin Trans. 2 2001, 1742-1747.
21. S. Z. Cao, M. Lin, Q. Zhang, Y. Mo, J. Phys. Chem. A 2004, 108, 4277-4282 for recent relevant computational work on solvation, and references to the earlier literature.
22. See, for example: B. Wilson, R. Georiadis, J. E. Bartmess, J. Am. Chem. Soc. 1991, 113, 1762-1769.
23. See, for example A. Bagno, R. L. Boso, N. Ferrari, G. Scorrano, Eur. J. Org. Chem. 1999, 1507-1515.
24. S. Böhm, M. Decouson, O. Exner, J.-F. Gal, P.-C. Maria, J. Org. Chem. 1994, 59, 8127-8131.
25. M. Canle, I. Demirtas, A. Freire, H. Maskill, M. Mishima, Eur. J. Org. Chem. 2004, 5031-5039.
26. a) E. P. L. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data, 1998, 27, 413-457;
27. b) E. P. Hunter, S. G. Lias in NIST Chemistry WebBook, NIST Standard Reference Database, 69, Ed. W. G. Mallard, National Institute of Standards and Technology, Gaithersburg, MD, 2003 (http://webbook.nist.gov).
28. a) D. H. Aue, M. T. Bowers, Gas Phase Ion Chemistry (Ed.: M. T. Bowers), Academic Press, New York, 1979, Vol. 2, pp. 2-51;
29. b) M. Mishima, M. Fujio, Y. Tsuno, Bull. Chem. Soc. Jpn. 1996, 69, 2009-2018.
30. Gaussian 98, Revision A.5, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
31. Z. B. Maksić, R. Vianello, J. Phys. Chem. A 2002, 106, 419-430.
32. Z. B. Maksić, M. Eckert-Maksić, in Theoretical and Computational Chemistry (series Eds.: P. Politzer, Z. B. Maksić), vol. 5,
33. Theoretical Organic Chemistry (Ed.: C. Parkanyi), Elsevier, Amsterdam, 1998, p. 203 and references cited therein.
34. Z. B. Maksić, R. Vianello, ChemPhysChem 2002, 3, 696-700.
35. C. A. Deakyne, Int. J. Mass Spectrom. 2003, 227, 601-616.
36. a) R. Vianello, Z. B. Maksić, J. Phys. Org. Chem. 2005, 18, 699-705;
37. b) R. Vianello, Z. B. Maksić, Tetrahedron 2006, 62, 3402-3411.
38. R. Vianello, Z. B. Maksić, Inorg. Chem. 2005, 44, 1095-1102.
39. T. Koopmans, Physica 1933, 1, 104-113.
40. S. G. Lias, Ionization Energy Evaluation, in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, (Eds.: P. J. Linstrom, W. G. Mallard), June 2005, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
41. Z. B. Maksić, B. Kovačević, J. Chem. Soc., Perkin Trans. 2 1999, 2623-2629.