Crystal and electronic structure of stable nitrenium ions. A comparison with structurally related carbenes

Journal of the American Chemical Society

Volumn 118, Issue 21, 1996, Pages 4925-4930

  Boche, Gernot ^a   Andrews, Phil ^a   Harms, Klaus ^a   Marsch, Michael ^a   Rangappa, Kanchugarakoppal S ^a   Schimeczek, Michael ^a   Willeke, Christoph ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; ELECTRONIC STRUCTURE; ORGANIC COMPOUNDS; STABILITY; X RAY CRYSTALLOGRAPHY;

CARBENES; NITRENIUM IONS;

IONS;

CARCINOGEN; NITROGEN DERIVATIVE;

ARTICLE; CARCINOGENICITY; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MOLECULAR STABILITY; X RAY CRYSTALLOGRAPHY;

EID: 15844402824     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9536274     Document Type: Article

References (88)

1. Gassman, P. G.; Acc. Chem. Res. 1970, 3, 26-33.
2. Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, 1984; pp 297-357.
3. Simonova, T. P; Nefedov, V. D.; Toropova, M. A.; Kirillov, N. F. Russ. Chem. Rev. 1992, 61, 584-599.
4. Bursey, M. M.; Harvan, D. J.; Parker, C. E.; Darden, T. A.; Hass, J. R. Organ. Mass. Spectr. 1983, 18, 530-533.
5. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
6. Miller, J. A. Cancer Res. 1970, 30, 559-576.
7. Kriek, E. Biochem. Biophys. Acta 1974, 355, 177-203.
8. Scribner, J. D.; Naimy, N. K. Cancer Res. 1975, 35, 1416-1421.
9. Famulok, M.; Bosold, F.; Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 337-338.
10. Famulok, M.; Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 468-469.
11. Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513-4514.
12. Robbins, R. J.; Yang, L. L.-N.; Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 6544-6552; see also refs 13 and 14.
13. Fishbein, J. C.; McClelland, R. A. J. Am. Chem. Soc. 1987, 109, 2824-2825.
14. Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
15. Cowley, A. H.; Cushner, M. C.; Lattman, M.; McKee, M. L.; Szobota, J. S.; Wilburn, J. C. Pure Appl. Chem. 1980, 52, 789-797.
16. Cowley, A. H.; Kemp, R. A. Chem. Rev. 1985, 85, 367-382.
17. Sanchez, M.; Mazières, M.-R.; Lamandé, L.; Wolf, R. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: Stuttgart, 1990; pp 129-148.
18. +.
19. Schoeller, W. W.; Busch, T. Chem. Ber. 1990, 123, 971-973.
20. Burford, N.; Losier, P.; Bakshi, P. K, Cameron, T. S. J. Chem. Soc., Dalton Trans. 1993, 201-202; Burford, N.; Losier, P.; Sereda, S. V.; Cameron, T. S.; Wu, G. J. Am. Chem. Soc. 1994, 116, 6474-6475.
21. Burford, N.; Losier, P.; Bakshi, P. K, Cameron, T. S. J. Chem. Soc., Dalton Trans. 1993, 201-202; Burford, N.; Losier, P.; Sereda, S. V.; Cameron, T. S.; Wu, G. J. Am. Chem. Soc. 1994, 116, 6474-6475.
22. David, G.; Niecke, E.; Nieger, M.; Radseck, J.; Schoeller, W. W. J. Am. Chem. Soc. 1994, 116, 2191-2192.
23. (a) Gudat, D.; Schrott, M.; Nieger, M. J. Chem. Soc., Chem. Commun. 1995, 1541-1542.
24. (b) Gudat, D.; Nieger, M.; Schrott, M. Chem. Ber. 1995, 128, 259-266.
25. (c Nakazawa, H.; Yamaguchi, Y.; Mizuta, T.; Miyoshi, K. Organometallics 1995, 14, 4173-4182.
26. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363. The bond angles at the carbene carbon atom and the bond lengths C(carbene)-N were compared with those in the corresponding "amidinium" cation.
27. Arduengo, A. J., III; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
28. Dixon, D. A.; Arduengo, A. J., III J. Phys. Chem. 1991, 95, 4180-4182.
29. Arduengo, A. J., III; Bock, H.; Chen, H.; Denk, M.; Dixon, D. A.; Green, J. C.; Herrmann, W. A.; Jones, N. L.; Wagner, M.; West, R. J. Am. Chem. Soc. 1994, 116, 6641-6649.
30. Arduengo, A. J., III; Rasika Dias, H. V.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812-6822.
31. Denk, M.; Lennon, R.; Hayashi, R.; West, R.; Belyakov, A. V.; Verne, H. P.; Haaland, A.; Wagner, M.; Metzler, N. J. Am. Chem. Soc. 1994, 116, 2691-2692.
32. Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F. R.; Bock, H.; Soluki, B.; Wagner, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1485-1488.
33. Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75.
34. Krollpfeiffer, F.; Rosenberg, A.; Mühlhausen, C. Ann. Chem. 1935, 515, 113-130.
35. (a) Wiley, R. H.; Moffat, J. J. Am. Chem. Soc. 1955, 77, 1703-1704.
36. (b) Wiley, R. H.; Hassung, K. F.; Moffat, J. J. Org. Chem. 1956, 21, 190-192.
37. Hansen, H.; Hünig, S.; Kishi, K. Chem. Ber. 1979, 112, 445-461.
38. Finley, K. T. In Heterocyclic Compounds; Montgomery, J. A., Ed.; John Wiley: New York, 1981; Vol. 39, pp 292-311.
39. -.
40. - distances as determined by X-ray crystallography are systematically too long, condition 2. is even better fulfilled than indicated by the experimental data.
41. (b) Jeffrey, G. A.; Maluszynska, H.; Mitra, J. Int. J. Biol. Macromol. 1985, 7, 336-348.
42. van der Waals radii: C 170, H 120, I 198 pm: Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
43. Peeters, O. M.; Schuerman, G. S.; Blaton, N. M.; De Ranter, C. J. Acta Cryst. 1993, C49, 1958-1961.
44. Boche, G.; Hilf, C.; Marsch, M.; Harms, K.; Lohrenz, J. C. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 487-489.
45. Boche, G.; Hilf, C.; Andrews, P. C., Harms, K.; Marsch, M., unpublished results.
46. Gobbi, A.; Frenking, G. Bull. Chem. Soc. Jpn. 1993, 66, 3153-3165.
47. Cramer, C. J.; Dulles, F. J.; Falvey, D. E. J. Am. Chem. Soc. 1994, 116, 9787-9788.
48. Arduengo, A. J., III; Dixon, D. A.; Kumashiro, K. K.; Lee, C.; Power, W. P.; Zilm, K. W. J. Am. Chem. Soc. 1994, 116, 6361-6367.
49. Cioslowski, J. Int. J. Quantum Chem.: Quantum Chem. Symp. 1993, 27, 309-319.
50. Heinemann, C.; Thiel, W. Chem. Phys. Lett. 1994, 217, 11-16. The C=C bond dissociation energy of the dimer of 3a is only 1 kcal/mol, while it is 31.2 kcal/mol for the dimer of 4a.
51. Nyulászi, L.; Kárpáti, T.; Veszprémi, T. J. Am. Chem. Soc. 1994, 116, 7239-7242.
52. Heinemann, C.; Herrmann, W. A.; Thiel, W. J. Organomet. Chem. 1994, 475, 73-84.
53. Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. The Stability of Imidazol-3-ylidenes and their Silicon Analogues. J. Am. Chem. Soc. 1996, 118, 2023-2038.
54. Boehme, C.; Frenking, G. The Electronic Structure of Stable Carbenes, Silylenes and Germylenes. J. Am. Chem. Soc. 1996, 118, 2039-2046. We are grateful to the authors of refs 48 and 49 for a preprint.
55. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
56. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
57. Whinnery, J. E.; Watson, W. H.; Acta Cryst. 1972, B28, 3635-3640. See also ref 53.
58. Abraham, D. J.; Rutherford, J. S.; Rosenstein, R. D. J. Med. Chem. 1969, 12, 189.
59. Boche, G.; Rangappa, K. S.; Marsch, M.; Harms, K. Z. Kristallogr. In press.
60. Kluger, R., Chem. Rev. 1987, 87, 863-876.
61. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
62. Schnellenberger, A. Ann. N. Y. Acad. Sci. 1982, 378, 51.
63. Suckling, C. J. Chem. Soc. Rev. 1984, 13, 97-129.
64. Stetter, H.; Kuhlmann, H. Angew. Chem., Int. Ed. Engl. 1974, 13, 539.
65. Matsumoto, T.; Ohishi, M.; Inoue, S. J. Org. Chem. 1985, 50, 603-606.
66. Jones, P. G.; Kennard, O. Acta Cryst. 1978, B34, 335-337.
67. Kutzelnigg, W., Isr. J. Chem. 1980, 19, 193-200.
68. Schindler, M.; Kutzelnigg, W. J. Chem. Phys. 1982, 76, 1919-1933.
69. (a) Schleyer, P.v.R.; Freeman, P. K.; Jiao, H.; Goldfuss, B. Angew. Chem. Int. Ed. Engl. 1995, 34, 337-340.
70. (b) Goldfuss, B.; Schleyer, P.v.R. Organometallics 1995, 14, 1553-1555.
71. Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Mühlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298-5306.
72. Chestnut, D. B.; Quin, L. D. J. Am. Chem. Soc. 1994, 116, 9638-9643.
73. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; Wiley: New York, 1994.
74. 43
75. The X-ray crystal structure data of 1,3-dibenzyl-1,2,3-triazolium iodide, which confirm nicely the results reported in this publication, have been accepted by Z. Kristallogr. (Boche, G.; Willeke, C.; Marsch, M.; Harms, K.).
76. +, are called carbocations: Thauer, R. K.; Berkessel, A. Angew. Chem., Int. Ed. Engl. 1995; 34, 2247-2250. See, also: Chem. Eng. News 1995, October 30, 7.
77. +, are called carbocations: Thauer, R. K.; Berkessel, A. Angew. Chem., Int. Ed. Engl. 1995; 34, 2247-2250. See, also: Chem. Eng. News 1995, October 30, 7.
78. Hurd, R. E.; John, B. K. J. Magn. Reson. 1991, 91, 648-653.
79. 15N NMR spectra.
80. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
81. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
82. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
83. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
84. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
85. TURBOMOLE: (a) Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104-111. (b) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, M. C. Chem. Phys. Lett. 1989, 162, 165-169. (c) Horn, H.; Weiss, H.; Häser, M.; Ehring, M.; Ahlrichs, R. J. Comput. Chem. 1991, 12, 1058-1064. (d) Häser, M.; Almlöf, J.; Feyereisen, M. W. Theor. Chim. Acta 1991, 79, 115-122. (e) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577. (d) Häser, M.; Ahlrichs, R.; Baron, H. P.; Weiss P.; Horn. H. Theor. Chim. Acta 1992, 83, 455-470.
86. GAUSSIAN 92, Revision F.3; Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; and Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1992.
87. (a) Kutzelnigg, W. Isr. J. Chem. 1980, 19, 193-200.
88. (b) Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR, Basic Principles and Progress; Springer: Berlin, Heidelberg, 1990; Vol. 23, pp 168-262.