Are mesoionic compounds aromatic?

Canadian Journal of Chemistry

Volumn 76, Issue 6, 1998, Pages 869-872

  Simas, Alfredo Mayall ^a   Miller, Joseph ^a,b   De Athayde Filho, Petrônio Filgueiras ^a,c  

^a DEPARTAMENTO DE QUÍMICA FUNDAMENTAL   (Brazil)

^b FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^c UNIVERSIDADE FEDERAL RURAL DE PERNAMBUCO   (Brazil)

Author keywords

Aromaticity; Betaines; Mesoionic compounds

Indexed keywords

AMPHOLYTE; AROMATIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; ELECTRON TRANSPORT; MATHEMATICAL COMPUTING; STRUCTURE ANALYSIS; THEORY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0031766670     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v98-065     Document Type: Article

References (50)

1. E. Fischer and E. Besthorn. J. Liebigs Ann. 212, 316 (1882).
2. (a) M. Busch. Ber. dt. Chem. Ges. 28, 2635 (1895)
3. (b) J. Prakt. Chem. 60, 225 (1899)
4. (c) Ber. dt. Chem. Ges. 38, 856 (1905) Ber. dt. Chem. Ges. 38, 4049 (1905)
5. (c) Ber. dt. Chem. Ges. 38, 856 (1905) Ber. dt. Chem. Ges. 38, 4049 (1905)
6. (d) J. Prakt. Chem. 74, 533 (1906).
7. W. Baker and W.D. Ollis. Quart. Rev. 11, 15 (1957).
8. Y. Noël. Bull. Soc. Chim. Fr. 173 (1964).
9. F.H.C. Stewart. Chem. Rev. 64, 129 (1964).
10. R. Huisgen. Chem. Soc. Spec. Publ. 21, 51 (1967).
11. L.B. Kier and E.B. Roche. J. Pharm. Sci. 56, 149 (1969).
12. N. Sucia. Stud. Cercet. Chim. 16, 117 (1968).
13. M. Ohta and H. Kato. In Nonbenzenoid aromatics. Edited by J.P. Snyder. Academic Press, New York. 1969.
14. W.D. Ollis and C.A. Ramsden. Adv. Heterocycl. Chem. 19, 1 (1976).
15. (a) C.A. Ramsden. Compr. Org. Chem. 4, 1171 (1979); (b) W.D. Ollis, S.P. Stanforth, and C.A. Ramsden. Tetrahedron, 41, 2239 (1985).
16. (a) C.A. Ramsden. Compr. Org. Chem. 4, 1171 (1979); (b) W.D. Ollis, S.P. Stanforth, and C.A. Ramsden. Tetrahedron, 41, 2239 (1985).
17. J.C. Earl and A.W. Mackney. J. Chem Soc. 899 (1935).
18. A.J. Schönberg. J. Chem Soc. 824 (1938).
19. W. Baker, W.D. Ollis, and V.D. Poole. J. Chem Soc. 307 (1949).
20. A.R. Katritzky. Chem. Ind. (London), 521 (1955).
21. K.T. Potts. Lect. Heterocycl. Chem. 4, 53 (1978).
22. M.J.S. Dewar and I.J. Turchi. J. Chem. Soc. Perkin Trans. 2, 548 (1976).
23. L.E. Orgel, T.L. Cottrell, W. Dick, and L.E. Sutton. Trans. Faraday Soc. 47, 113 (1951).
24. L. Paoloni. Gazz. Chim. Ital. 96, 83 (1966).
25. D.A. Bochvar and A.A. Bagatur' yants. Zh. fiz. Khim. 39, 1631 (1985); Chem. Abstr. 64, 3328 (1966).
26. D.A. Bochvar and A.A. Bagatur' yants. Zh. fiz. Khim. 39, 1631 (1985); Chem. Abstr. 64, 3328 (1966).
27. H.C. Longuet-Higgins. J. Chim. Phys. Phys.-Chim. Biol. 46, 244 (1949).
28. L.B. Kier. Tetrahedron Lett. 1233 (1967).
29. L.B. Kier and E.B. Roche. J. Pharm. Sci. 55, 807 (1968).
30. J.E. Bloor, B.R. Bilson, and F.P. Billlingsley. Theor. Chim. Acta, 12, 360 (1968).
31. M. Barber, S.J. Broadbent, J.A. Connor, M.F. Guest, H. Millier, and H.J. Paxley. J. Chem. Soc. Perkin Trans. 2, 1517 (1972).
32. T.L. Chan, J. Miller, and F. Stansfield. J. Chem. Soc. 1213 (1964).
33. V.R. Braz, A. Echevarria, and J. Miller. Heterocycl. Commun. 2, 507 (1996).
34. A. Echevarria and J. Miller. J. Chem. Soc. Perkin Trans. 2, 1425 (1989).
35. A. Echevarria. Doctoral thesis, University of São Paulo, Brazil. 1986.
36. G.A. Olah, D.P. Kelly, and N. Sucia. J. Am. Chem. Soc. 92, 3133 (1970).
37. P.F. de Athayde Filho, J. Miller, and A.M. Simas. Chimia, 51, 453 (1997).
38. (a) K-K. Cheung, S.E. Galembeck, J. Miller, M.B. de Oliveira, A.B. Pereira, and A.M. Simas. Acta Crystallogr. Sect. C, C47, 2630 (1991)
39. (b) Acta Crystallogr. Sect. C, C48, 523 (1992).
40. K-K. Cheung, A. Echevarria, S.E. Galembeck, M.A.M. Maciel, J. Miller, V.M. Rumjanek, and A.M. Simas. Acta Crystallogr. Sect. C, C48, 1471 (1992).
41. G.L.C. Moura. Masters thesis, Federal University of Pernambuco, Brazil. 1996.
42. F.M.C. Stewart and N. Danieli. Chem. Ind. (London), 1926 (1962).
43. G.H. Schmid. J. Mol. Struct. 5, 236 (1970).
44. G.W. Evans and B. Milligan. Aust. J. Chem. 20, 1779 (1967).
45. A.Ya. Lazaris and A.N. Egorochkin. Izv. Akad. Nauk SSSR Ser. Khim. 8, 1870 (1979).
46. M. Begtrup. J. Chem Soc. Perkin Trans. 1, 1132 (1979).
47. (a) J. Jaz′win′ski, O. Staszewska, L. Stefaniak, and G.A. Webb. Magn. Reson. Chem. 33, 134 (1995);
48. (b) J. Mol Struct. 377, 167 (1996).
49. J. Miller, M.B. de Oliveira, A.B. Pereira, S.E. Galembeck, G.L.C. Moura, and A.M. Simas. Phosphorus Sulfur Silicon Relat. Elem. 108, 75 (1996).
50. G. Gilchrist. In Heterocyclic chemistry. 2nd ed. Wiley, N.Y. 1992. p. 329.