Reaction of CH3NO3 with resonance stabilized anions the gas-phase counterpart of alkyl nitrate nitration in solution

International Journal of Mass Spectrometry and Ion Processes

Volumn 164, Issue 1-2, 1997, Pages 121-131

  Ricci, A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Alkyl nitrate nitration; Ion cyclotron resonance; Methyl nitrate; Negative ions; Resonance stabilized anions

Indexed keywords

EID: 0005132598     PISSN: 01681176     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0168-1176(97)00051-7     Document Type: Article

References (43)

1. (a) M. Attinà, F. Cacace, J. Am. Chem. Soc. 108 (1986) 318;
2. (b) M. Attinà, F. Cacace, M. Yañez, J. Am. Chem. Soc. 109 (1987) 5092;
3. (c) M. Attinà, F. Cacace, G. De Petris, Angew. Chemie Int. Ed. Engl. 26 (1987) 1177.
4. K.J. Szabo', A.B. Hörnfeldt, S. Gronowitz, J. Am. Chem. Soc. 114 (1992) 6827.
5. M. Aschi, M. Attinà, F. Cacace, A. Ricci, J. Am. Chem. Soc. 116 (1994) 9535.
6. J.E. Bartmess, R.M. Georgiadis, Vacuum 33 (1983) 149.
7. T. Su, M.T. Bowers, Int. J. Mass Spectrom. Ion Phys. 12 (1973) 347.
8. (a) W.N. Olmstead, J.I. Brauman, J. Am. Chem. Soc. 99 (1977) 4219;
9. (b) O.I. Asubiojo, J.I. Brauman, J. Am. Chem. Soc. 101 (1979) 3715;
10. (c) M.J. Pellerite, J.I. Brauman, J. Am. Chem. Soc. 102 (1980) 5993;
11. (d) G. Caldwell, T.F. Magnera, P. Kebarle, J. Am. Chem. Soc. 106 (1984) 959;
12. (e) C.-C. Han, J.A. Dodd, J.I. Brauman, J. Phys. Chem. 90 (1986) 471;
13. (f) C.H. De Puy, G. Scott, A. Mullin, V.M. Bierbaum, J. Am. Chem. Soc. 112 (1990) 8650;
14. (g) D.M. Cyr, L.A. Posey, G.A. Bishea, C.-C. Han, M.A. Johnson, J. Am. Chem. Soc. 113 (1991) 9697;
15. (h) W.B. Knighton, J.A. Bognar, P.M. O'Connor, E.P. Grimsrud, J. Am. Chem. Soc. 115 (1993) 12 079.
16. (a) D.K. Bohme, L.B. Young, J. Am. Chem. Soc. 92 (1970) 7354;
17. (b) J.I. Brauman, C.A. Lieder, M.J. Wite, J. Am. Chem. Soc. 95 (1973) 927;
18. (c) W.E. Farneth, J.I. Brauman, J. Am. Chem. Soc. 98 (1976) 5546;
19. (d) M.J. Pellerite, J.I. Brauman, J. Am. Chem. Soc. 105 (1983) 2672;
20. (e) C.-C. Han, J.I. Brauman, J. Am. Chem. Soc. 111 (1989) 6491;
21. (f) R.A.L. Peerboom, L.J. de Koning, N.M.M. Nibbering, J. Am. Soc. Mass Spectrom. 5 (1994) 159.
22. W.H. Saunders Jr., , J.E. Van Verth, J. Org. Chem. 60 (1995) 3452.
23. (a) M.D. Brickhouse, R.R. Squires, J. Phys. Org. Chem. 2 (1989) 389;
24. (b) R.R. Squires, Acc. Chem. Res. 25 (1992) 461.
25. (a) I.L. Freriks, L.J. de Koning, N.M.M. Nibbering, J. Am. Chem. Soc. 113 (1991) 9119;
26. (b) I.L. Freriks, L.J. de Koning, N.M.M. Nibbering, J. Phys. Org. Chem. 5 (1992) 776.
27. S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, W.G. Mallard, J. Phys. Chem. Ref. Data 17 (1988) 1.
28. J. Kaneti, P.v.R. Schleyer, T. Clark, A.J. Kos, G.W. Spitznagel, J.G. Andrade, J.B. Moffat, J. Am. Chem. Soc. 108 (1986) 1481.
29. G. Boche, Angew. Chem. Int. Ed. Engl. 28 (1989) 277.
30. M.T. Reetz, S. Hutte, R. Goddard, J. Am. Chem. Soc. 115 (1993) 9339.
31. G.K. King, M.M. Maricq, V.M. Bierbaum, C.H. DePuy, J. Am. Chem. Soc. 103 (1981) 7133.
32. M.J.S. Deward and R.C. Dougherty, The PMO Theory of Organic Chemistry, Plenum, New York, 1975, pp. 212-220.
33. M. Meot-Ner, S.A. Kafafi, J. Am. Chem. Soc. 110 (1988) 6297.
34. (a) A.T. Nielsen, in: H. Feuer (Ed.), The Chemistry of Nitro and Nitroso Compounds, Interscience, New York, 1969, Part 1, p. 349;
35. (b) H. Feuer, in: S. Patai (Ed.), Supplement F: The Chemistry of Amino, Nitoso and Nitro Compounds and their Derivatives, Ch. 19, Wiley, New York, 1982, p. 806.
36. K. Lammertsma, B.V. Prasad, J. Am. Chem. Soc. 115 (1993) 2348.
37. (a) A.J. Noest, N.M.M. Nibbering, Int. J. Mass Spectrom. Ion Phys. 34 (1980) 383.
38. (b) G. Klass, J.H. Bowie, Aust. J. Chem. 33 (1980) 2271;
39. (c) J.H.J. Dawson, N.M.M. Nibbering, Int. J. Mass Spectrom. Ion Phys. 33 (1980) 3.
40. (a) R.R. Squires, C.H. DePuy, Org. Mass Spectrom. 17 (1982) 187;
41. (b) L.J. Chyall, M.D. Brickhouse, M.E. Schnute, R.R. Squires, J. Am. Chem. Soc. 116 (1994) 8681.
42. J.B. Pedley, R.D. Naylor, S.P. Kirby, Thermodynamical Data of Organic Compounds, 2nd edn, Chapman and Hall, London, 1986.
43. V.I. Pepekin, Y.A. Lebedev, A.A. Fainzilberg, G.G. Rozantsev, A.Y. Apin, Russ. J. Phys. Chem. 43 (1969) 1454.