Substituent effects on two-center three-electron bonds and hydrogen bonds involving unsaturated organic functional groups and an ammonia radical cation - The resonance contribution

Chemistry - A European Journal

Volumn 6, Issue 9, 2000, Pages 1592-1600

  Humbel, Stéphane ^a   Hoffmann, Norbert ^a   Côte, Isabelle ^a   Bouquant, James ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Ab initio calculations; Hydrogen bonds; Ion molecule complex; Resonance model

Indexed keywords

AMMONIA; FUNCTIONAL GROUP; NITROGEN;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; ELECTRON TRANSPORT; EXPERIMENTAL MODEL; HYDROGEN BOND; REACTION ANALYSIS;

EID: 0034595259     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000502)6:9<1592::AID-CHEM1592>3.3.CO;2-N     Document Type: Article

References (47)

1. a) P. M. Gill, L. Radom, J. Am. Chem. Soc. 1998, 110, 4931
2. b) T. Clark, J. Am. Chem. Soc. 1988, 110, 1672.
3. a) Y. Wang, Chem. Phys. Lett. 1985, 116, 286
4. b) W. Hub, S. Schneider, F. Dörr, J. D. Oxman, F. D. Lewis, J. Am. Chem. Soc. 1984, 106, 701.
5. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
6. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
7. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
8. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
9. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
10. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
11. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
12. See for instance: a) L. S. Nichols, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1998, 120, 1538 b) S. P. de Visser, L. J. de Konning, N. M. M. Nibbering, J. Am. Chem. Soc. 1998, 120, 1517 c) K.-D. Asmus, Acc. Chem. Res. 1979, 12, 436 d) K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwish, J. Am. Chem. Soc. 1979, 101, 5322 e) Y. Deng, A. J. Illies, M. A. James, M. L. McKee M. Peschke, J. Am. Chem. Soc. 1995, 117, 420 f) J. C. Scaiano, S. Garcia, H. Garcia, Tetrahedron Lett. 1997, 38, 5929 g) R. W. Alder, Acc. Chem. Res. 1983, 16, 321 h) W. Wang, M. N. Schuchmann, H.-P. Schuchmann, W. Knolle, J. von Sonntag, C. von Sonntag, J. Am. Chem. Soc. 1999, 121, 238.
13. a) S. Humbel, P. C. Hiberty, I. Demachy, Chem. Phys. Lett. 1995, 247, 126
14. b) P. C. Hiberty, S. Humbel, S. Shaik, D. Danovitch, J. Am. Chem. Soc. 1995, 117, 9003.
15. N. C. Baird, J. Chem. Educ. 1977, 54 291.
16. P. C. Hiberty, S. Humbel, P. Archirel, J. Phys. Chem. 1994, 98, 11 697.
17. For cationic systems see: a) M. Bonifacic, I. Stefanic, G. L. Hug, D. A. Armstrong, K.-D. Asmus. J. Am. Chem. Soc. 1998, 120, 9930 b) K. Bobrowsky, G. L. Hug, B. Marciniak, B. Miller, C. Schöneich, J. Am. Chem. Soc. 1997, 119, 8000 c) M. A. James, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1996, 118, 7836; for neutral systems see d) M. L. McKee, A. Nicolaides, L. Radom, J. Am. Chem. Soc. 1996, 118, 10571.
18. For cationic systems see: a) M. Bonifacic, I. Stefanic, G. L. Hug, D. A. Armstrong, K.-D. Asmus. J. Am. Chem. Soc. 1998, 120, 9930 b) K. Bobrowsky, G. L. Hug, B. Marciniak, B. Miller, C. Schöneich, J. Am. Chem. Soc. 1997, 119, 8000 c) M. A. James, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1996, 118, 7836; for neutral systems see d) M. L. McKee, A. Nicolaides, L. Radom, J. Am. Chem. Soc. 1996, 118, 10571.
19. For cationic systems see: a) M. Bonifacic, I. Stefanic, G. L. Hug, D. A. Armstrong, K.-D. Asmus. J. Am. Chem. Soc. 1998, 120, 9930 b) K. Bobrowsky, G. L. Hug, B. Marciniak, B. Miller, C. Schöneich, J. Am. Chem. Soc. 1997, 119, 8000 c) M. A. James, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1996, 118, 7836; for neutral systems see d) M. L. McKee, A. Nicolaides, L. Radom, J. Am. Chem. Soc. 1996, 118, 10571.
20. For cationic systems see: a) M. Bonifacic, I. Stefanic, G. L. Hug, D. A. Armstrong, K.-D. Asmus. J. Am. Chem. Soc. 1998, 120, 9930 b) K. Bobrowsky, G. L. Hug, B. Marciniak, B. Miller, C. Schöneich, J. Am. Chem. Soc. 1997, 119, 8000 c) M. A. James, M. L. McKee, A. J. Illies, J. Am. Chem. Soc. 1996, 118, 7836; for neutral systems see d) M. L. McKee, A. Nicolaides, L. Radom, J. Am. Chem. Soc. 1996, 118, 10571.
21. S. Humbel, I. Côte, N. Hoffmann, J. Bouquant, J. Am. Chem. Soc. 1999, 121, 5507.
22. The 2c-3e complex must involve the radical and the lone pair of the organic substrate. An interaction with the system is not favorable, since such an interaction would partly depopulate a bonding orbital (low in energy).
23. There is a subtle difference between these terms. See, for example, Y. Pan, M. A. McAllister, J. Am. Chem. Soc. 1998, 120, 166.
24. a) S. Scheiner, T. Kar, J. Am. Chem. Soc. 1995, 117, 6970
25. b) S. Scheiner, J. Am. Chem. Soc. 1981, 103, 315.
26. J. Fossey, personal communication (1999).
27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision E.2, Gaussian, Pittsburgh PA, 1995.
28. D. E. Woon, T. H. Dunning, Jr., J. Chem. Phys. 1993, 90, 1358.
29. Five d orbitals were used with this aug-cc-pvdz basis set (5D).
30. a) S. Humbel, S. Sieber, K. Morokuma, J. Chem. Phys. 1996, 105, 1959
31. b) S. Dapprich, I. Komaromi, K. S. Byun, K. Morokuma, J. Mol. Struct. (THEOCHEM) 1999, 461-462, 1.
32. When comparing PMP3/6-31G(d,p)//MP2/6-31G(d) and the IMO-MO-ONIOM: CCSD(T):MP2/6-31G(d,p)//MP2/6-31G(d) levels. See S. Humbel, J. Mol. Struct. (THEOCHEM) 1999, 461-462, 153.
33. See, for example, a) S. Scheiner, L. Wang, J. Am. Chem. Soc. 1993, 115, 1958
34. b) E. Uggerud, J. Am. Chem. Soc. 1996, 116, 6873.
35. s structures. The potential energy surface is extremely flat vis-à-vis the corresponding coordinates. We kept only the most symmetrical one for the high-level calculations.
36. -1.
37. M. Meot-Ner, J. Am. Chem. Soc. 1984, 106 1257.
38. J. W. Larson, T. B. McMahon, J. Am. Chem. Soc. 1982, 106, 6255.
39. a) R. A. Marcus, J. Phys. Chem. 1968, 72, 891
40. b) A. J. Kresge, Acc. Chem. Res. 1975, 354
41. c) O. Cohen, R. A. Marcus J. Phys. Chem. 1968, 72, 4249.
42. a) S. Scheiner, P. Redfern, J. Phys. Chem. 1986, 90, 2969
43. b) D. E. Magnoli, J. R. Murdoch, J. Am. Chem. Soc. 1981, 103, 7465, and references therein.
44. Similar behavior can be found in anionic species, see, for example, M. Garcia-Viloca, A. Gonzalez-Lafont, J. M. Lluch, J. Am. Chem. Soc. 1997, 119, 1081.
45. BH+B respectively.
46. BH+B√).
47. AH+A in these cases.