Why do nitroso compounds dimerize while their oxime tautomers do not? A structural study of the trans-dimer of 2-chloro-2-methyl-3-nitrosobutane and higher level ab initio study of thermodynamic stabilities and electronic structures of isomers of diazene dioxides

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1047-1058

  Glaser, Rainer ^a   Murmann, R Kent ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001369266     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950783k     Document Type: Article

References (86)

1. Allman, R. Structural Chemistry. In The Chemistry of the Hydrazo, Azo, and Azoxy Groups; Patai, S , Ed., John Wiley & Sons: New York, 1975; Chapter 2, Part 1, p 49ff.
2. (a) N,N-dimethyl-p-nitrosoaniline monomer: Rømming, C.: Talberg, H. J Acta Chem. Scand 1973, 27, 2246.
3. (b) (+)-10-Bromo-2-chloro-2-nitrocamphane: Ferguson, G.; Fritchie, C. J., Robertson, J. M.; Sim, G. A. J. Chem. Soc. 1961, 1976-1987.
4. X-ray structures of nitrosomethane dimer: (a) cis: Germain, G.; Piret, P.; Meerssche, M. van. Acta Crystallogr. 1963, 16, 109.
5. (b) trans: Meerssche, M. van: Germain, G. Bull. Soc. Chim. Belg. 1959, 68, 244.
6. Trans diazene dioxides: (a) p-Bromonitrosobenzene dimer: Darwin, C ; Hodgkin, D. C. Nature 1950, 166, 827.
7. (b) 2,4,6-Tribromonitrosobenzene dimer: Fenimore, C. P. J Am. Chem. Soc. 1930, 72, 3226.
8. (c) Trans dimer of 2-nitronitrosoethane: Boer, F. P.; Turley, J. W. J. Am. Chem. Soc. 1969, 91, 1371.
9. (d) Trans dimer of nitrosocyclohexane: Tanimura, M.; Kobori, K.; Kashiwagi, M.; Kinoshita, Y. Bull. Chem. Soc. Jpn. 1970, 43, 1962.
10. (e) trans-2,2′-Dicarboxyazobenzene dioxide: Dieterich, D. A.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1974, 96, 6372.
11. (f) (E)-1,2-Bis(I-nitro-1-methylethyl)diazene 1,2-dioxide: Tinant, B.; Declercq, J. P.; Exner, O. Bull Soc. Chim. Belg. 1987, 96, 149.
12. (g) Trans-dimeric 2-methyl-2-nitrosopropane: Gowenlock, B G.; McCullough, K. J.; Manson, R. B. J. Chem. Soc., Perkin Trans 2 1988, 701.
13. (h) trans-2,2′,6,6′-tetraisopropylazodioxybenzene: Gowenlock, B. G.; McCullough, K. J. J. Chem. Soc., Perkin Trans. 2 1989, 551.
14. 13C-NMR studies of monomeric 2-chloro-2-nitrosonorbornane and its diastereoisomerie trans-diazene dioxide dimers, see: Boucenna, M.-C.; Davidson, J S.; McKee, A.; Porte, A. L.; Apperley, D. C. J. Chem. Soc. Perkin Trans. 2 1995, 1381-1387.
15. (j) trans-N N′-dioxo-1,1′-azobismorbornanel: Greer, M. L.: Sarker. H.; Mendicino, M. E.; Blackstock, S. C. J. Am. Chem. Soc. 1995, 117, 10460-10467.
16. Cis diazene dioxides: (a) cis-azobenzene dioxide: Dieterich, D. A.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1974, 96, 6372.
17. (b) Cis dimer of pentafluoronitrosobenzene. Prout, C. K.; Coda, A.; Forder, R. A.; Kamenar, B. Cryst. Struct. Commun. 1974, 3, 39.
18. Cis diazene dioxides in ring systems: (a) 1,8-Dinitrosonaphthalene: Prout, C. K.; Cameron, T. S.; Dunn, R. M. A.; Hodder, O. J. R.; Viterbo, D. Acta Crystallogr. B 1971, 27, 1310.
19. (b) cis-Azodiquinoxaline dioxide: Armand, J.; Armand, Y.; Boulares, L.; Philoche-Levisalles, M.; Pinson, J. Can. J. Chem. 1981, 59, 1711.
20. 2,4]non-6-ene 6,7-dioxide: Prout, K.; Stothard, V. P.; Watkin, D. J. Acta Crystallogr., Sect. B 1978, 34, 2602.
21. (d) 1,3,4-Trifluoro-7,9-dimethyl-11H-pyrido-[4,3-c][1,2]benzodiazepine 5,6-dioxide: Banks, R. E.; Djebli, Y.; Fields, R.; Olawore, N. O.; Pritchard, R. G.; Tsiliopoulos, E.; Mason, J. J. Chem. Soc., Perkin Trans. 1 1989, 1117.
22. Morrison, H. A. The Photochemistry of the Nitro and Nitroso Groups. In The Chemistry of the Nitro and Nitroso Groups; Feuer, E., Ed., John Wiley & Sons: New York, 1969; Chapter 4, Part 1, p 165.
23. Murmann, R. K. J. Am. Chem. Soc. 1957, 79, 521.
24. Siripaisarnpipat, S.; Schlemper, E. O. Inorg. Chem. 1983, 22, 282.
25. (a) Fair, C. K.; Troutner, D. E.; Schlemper, E. O.; Murmann, R. K.; Hoppe, M. L. Acta Crystallogr. 1984, C40, 1544.
26. (b) Troutner, D. E.; Volkert, W. A.; Hoffman, T. J.; Holmes, R. A. Int. J. Radiat. Isot. 1984, 35, 467.
27. (c) Murmann, R. K.; Vassian, E. G. Coord. Chem. Rev. 1990, 105, 1.
28. (d) Murmann, R. K., unpublished results.
29. We recognize that dimer formations might involve N or O addition to the oxime C=N carbon, that bis-zwitterionic structures A-C might close to four-membered ring systems, and so on. We focus here on the tautomeric NN connected noncyclic systems A-D.
30. Bruna, P. J.; Marian, C. M Chem. Phys. Lett. 1979, 67, 109, and references cited there.
31. Sengupta, D.; Chandra, A. K. J. Chem. Phys. 1994, 101, 3906.
32. Mebel, A. M.; Morokuma, K.; Lin, M. C.; Melius, C. F. J. Phys. Chem. 1995, 99, 1900.
33. Guadagnini, R.; Schatz, G. C.; Walch, S. P. J. Chem. Phys. 1995, 102, 774.
34. (a) Mason, J.; Bronswijk, W. v. J. Chem Soc. A 1971, 791, and references cited therein.
35. (b) For a recent reference on hyponitrite chemistry, see: Caldwell, S. E ; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 8676-8677, and references cited therein.
36. Tilden, W. A. J. Chem. Soc. 1875, 28, 514.
37. Hoffmann, R.; Gleiter, R.; Mallory, F. B. J. Am. Chem. Soc. 1970, 92, 1461.
38. (a) Heiberg, A. B. Chem. Phys. 1977, 26, 309.
39. (b) Ibid. 1979, 43, 415.
40. Minato, T.; Yamabe, S.; Oda, H. Can. J. Chem. 1982, 60, 2740
41. (a) Luttke, W.; Shancke, P. N.; Traetteberg, M. Theor. Chim Acta 1994, 87, 321, and references cited therein.
42. (b) This article presents a well written and concise history of studies of the diazene dioxide formation.
43. For a pertinent recent discussion, see: Glaser, R.; Chen, G. S.; Anthamatten, M.; Barnes, C. L. J. Chem. Soc., Perkin Trans. 2 1995, 1449.
44. International Tables for X-Ray Crystallography; Kynoch Press, Birmingham (Present distributor: Kluwer Academic Publishers, Dordrecht): Vol. IV.
45. Frenz, B. A. Enraf-Nonius Structure Determination Package. Enraf-Nonius Delft. The Netherlands, 1985.
46. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley & Sons: New York, 1986.
47. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quant Chem. 1978, 14, 91.
48. Glaser, R.; Choy, G. S.-C. J. Phys Chem. 1993, 97, 3188, and references cited there.
49. Hout, R. F.; Levi, B. A.; Hehre, W. J. J. Comput. Chem. 1982, 3, 234.
50. Vibrate 2.0: Glaser, R.; Chladny, B. S.; Hall, M. K. Quantum Chemistry Program Exchange, QCPE Bulletin 1993, 13, 75.
51. (a) Krishnan, R.; Pople, J. A. Int. J. Quant. Chem. 1978, 14, 91.
52. (b) Krishnan, R.; Frisch, M. J.; Pople, J. A. J. Chem. Phys. 1980, 72, 4244
53. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
54. Gaussian 92/DFT, Revision G.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, M. A. Robb, M. Head-Gordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1993, and references cited there
55. NBO review: Weinhold, F.; Carpenter, J. E. In The Structure of Small Molecules and Ions; Naaman, R., Vager, Z., Eds.; Plenum Press: New York, 1988; p 227ff.
56. Meinwald, J.; Meinwald, Y. C.; Baker, T. N., III. J. Am. Chem. Soc. 1964, 86, 4074.
57. Beckham, L. J.; Fessler, W. A.; Rise, M. A. Chem. Rev. 1951, 48, 319.
58. (a) Hickinbottom, W. J. Reactions of Organic Compounds; Longmans, Green & Co.: New York, 1936; pp 20-23.
59. (b) Wallach, O. Chem Ber. 1895, 28, 1308.
60. Thorne, N. J. Chem. Soc. 1956, 2587, 4271.
61. (a) March, J. Advanced Organic Chemistry, 3rd ed.; Wiley & Sons: New York, 1985; p 729.
62. (b) Ibid, p 18.
63. The closest intermolecular approach to hydrogen are approaches of N to HC3 (1.937(10), 2.347(12)) and of O to HC3 (2.174(15) A), and both of these are too far removed to be of structural importance.
64. 2: Hussein, M. S.; Hague, M. Acta Crystallogr. 1983, C39, 292.
65. (b) Structure of bis(2-methyl-3-butane oxime)hydrazine: Murmann, R. K.; Schlemper, E. O ; Barnes, C. L. J. Crystallogr. Spectrosc. Res. 1993, 23, 675.
66. (c) Crystal structure of 3-methyl-3-amino-2-butanone oxime (P21, a = 9.225, b = 10.937, c = 6.943, β = 106.5, V = 671.7, R = 0.04, Rw = 0.048). Murmann, R. K., to be published.
67. Efi, G. E.; Schlemper, E. O. Polyhedron 1991, 10, 1611.
68. 1(C2)] are small for all other respective frequencies.
69. (a) Dalby, F. W. Can. J. Phys. 1958, 36, 1336.
70. (b) Herzberg, G. Electronic Spectra of Polyatomic Molecules; Nostrand Reinhold Co.: New York, 1966: p 589.
71. MW structure and dipole moment of MeNO: Turner, P. H.; Cox, A. P. J. Chem. Soc., Faraday Trans. 2 1978, 74, 533.
72. Christie, M. I.; Frost, J. S.; Voisey, M. A. Trans. Faraday Soc. 1965, 61, 674.
73. See, for example, Table V in the paper by Dietrich, Paul, and Curtin (ref 4e).
74. Review of nitrosobenzene chemistry: Zuman, P.; Shah, B. Chem. Rev 1994, 94, 1621.
75. 5 excitations associated with rehybridization as in the case discussed here and numerous examples can be found in Herzberg's books on molecular spectroscopy.
76. Blackstone, S. C.; Poehling, K.; Greer, M. L. J Am. Chem. Soc. 1995, 117, 6617, and references cited therein.
77. (a) Luttke, W. Z. Elektrochem. 1957, 61, 302, 976.
78. (b) Kaissler, V. v.; Lüttke, W. Z. Elektrochem 1959, 63, 614.
79. (c) See also: Gowenlock, B. G.; Luttke, W. Quart Rev (London) 1958, 12, 321.
80. The earlier estimate of 8.7 Debye obtained at the RHF/4-31G level by Minato et al. greatly exceeds the value computed here at the correlated level. Note that the deviation is of about the same magnitude as for nitrosomethane for which a comparison between the experimental and theoretical dipote moments was made.
81. (a) Haddon, R. C. Tetrahedron Lett 1972, 37, 3897.
82. (b) Haddon, R. C.; Poppinger, D.; Radom, L. J. Am. Chem. Soc. 1975, 97, 1645, and references therein.
83. (c) Raine, G. P.; Schaefer, H. F.; Haddon, R. C. J. Am. Chem. Soc. 1983, 105, 194, and references therein.
84. dim = 59.8 kcal/mol.
85. Harcourt, R. C.; Skrezenek, F. L., Gowenlock, B. G. J. Mol. Struct (Theochem) 1993, 284, 87.
86. 2C=NOH has been reported: Duxbury, G.; Percival, R. M.; Devoy, D.; Mahmoud, M. R. M J. Mol Spectrosc 1988, 132, 380.