A unified orbital model of delocalised and localised currents in monocycles, from annulenes to azabora-heterocycles

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1257-1266

  Soncini, Alessandro ^a   Domene, Carmen ^b   Engelberts, Jeroen J ^c   Fowler, Patrick W ^a   Rassat, André ^d   Van Lenthe, Joop H ^c   Havenith, Remco W A ^c   Jenneskens, Leonardus W ^c  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c UTRECHT UNIVERSITY   (Netherlands)

^d ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Aromaticity; Boron; Nitrogen heterocycles; Ring current; Valence bond

Indexed keywords

CHEMICAL BONDS; CURRENT DENSITY; MAGNETIC FIELDS;

AZABORA-HETROCYCLES; ELECTRONEGATIVITY PARAMETERS; NITROGEN LOCALIZED CURRENTS; ORBIT MODELS;

AROMATIC COMPOUNDS;

ANNULENE DERIVATIVE; AROMATIC COMPOUND; BORANE DERIVATIVE; HETEROCYCLIC COMPOUND;

AB INITIO CALCULATION; ARTICLE; BINDING SITE; CALCULATION; CHEMICAL BINDING; CHEMICAL MODEL; CONJUGATION; DENSITY; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; HARTREE FOCK CALCULATION; MAGNETIC FIELD; MEMBRANE CURRENT; MOLECULAR MODEL; UNIFIED ORBITAL MODEL;

EID: 14544268551     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400678     Document Type: Article

References (50)

1. R. C. Haddon, J. Am. Chem. Soc. 1979, 101, 1722-1728.
2. P. W. Fowler, E. Steiner, J. Phys. Chem. A 1997, 101, 1409-1413.
3. E. Steiner, P. W. Fowler, J. Phys. Chem. A 2001, 105, 9553-9562.
4. E. Steiner, P. W. Fowler, Chem. Commun. 2001, 2220-2221.
5. E. Steiner, P. W. Fowler, R. W. A. Havenith, J. Phys. Chem. A 2002, 106, 7048-7056.
6. F. London, J. Phys. Radium 1937, 8, 397-409.
7. L. Pauling, J. Chem. Phys. 1936, 4, 673-677.
8. J. A. Pople, J. Chem. Phys. 1956, 24, 1111.
9. P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
10. H. C. Longuet-Higgins in Aromaticity, Special Publication No. 21, The Chemical Society, London, 1967, 109-110.
11. For recent summaries of the history of the discussion on the putative aromatic character of borazine, see, for example: a) M. A. M. Forgeron, D. L. Bryce, R. E. Wasylishen, R. Rosler, J. Phys. Chem. A 2003, 107, 726-735;
12. b) B. Kiran, A. K. Phukan, E. D. Jemmis, Inorg. Chem. 2001, 40, 3615-3618.
13. G. A. Anderson, J. J. Lagowski, Inorg. Chem. 1975, 14, 1845-1848.
14. A. J. Bridgeman, Polyhedron 1998, 17, 2279-2288.
15. For references to the chemistry, and to discussions on the possible aromaticity of these molecules, see: a) P. Paetzold, Phosphorus, Sulfur Silicon Relat. Elem. 1994, 93, 39-50;
16. b) E. von Steuber, G. Elter, M. Noltemeyer, H. G. Schmidt, A. Meller, Organometallics 2000, 19, 5083-5091.
17. R. C. Haddon, Pure Appl. Chem. 1982, 54, 1129-1142.
18. N. C. Baird, M. A. Whitehead, Can. J. Chem. 1967, 45, 2059-2070.
19. T. A. Keith, R. F. W. Bader, Chem. Phys. Lett. 1993, 270, 223-231.
20. S. Coriani, P. Lazzeretti, M. Malagoli, R. Zanasi, Theor. Chim. Acta 1994, 59, 181-192.
21. A. Soncini, P. W. Fowler, L. W. Jenneskens, Phys. Chem. Chem. Phys. 2004, 6, 277-284.
22. a) A. Matsuura, K. Komatsu, J. Am. Chem. Soc. 2001, 123, 1768-1769;
23. b) P. W. Fowler, R. W. A. Havenith, L. W. Jenneskens, A. Soncini, E. Steiner, Angew. Chem. 2002, 114, 1628-1630; Angew. Chem. Int. Ed. 2002, 41, 1558-1560.
24. b) P. W. Fowler, R. W. A. Havenith, L. W. Jenneskens, A. Soncini, E. Steiner, Angew. Chem. 2002, 114, 1628-1630; Angew. Chem. Int. Ed. 2002, 41, 1558-1560.
25. R. Daudel, R Lefebvre, C. Moser, Quantum Chemistry, Methods and Applications, Wiley-Interscience, New York, 1959, p. 449.
26. a) A. Streitwieser Jr., Molecular Orbital Theory for Organic Chemists, Wiley, New York, 1961;
27. b) N. C. Baird, M. A. Whitehead, Can. J. Chem. 1966, 44, 1933-1943.
28. R. McWeeny, Mol. Phys. 1958, 1, 311-321.
29. P. W. Fowler, E. Steiner, Chem. Phys. Lett. 2002, 364, 259-266.
30. a) H. S. Turner, R. J. Warne, Proc. Chem. Soc. London 1962, 69-70;
31. b) R. M. Minyaev, J. Struct. Chem. 2000, 41, 1-10.
32. T. M. Gilbert, B. D. Gailbreath, Organometallics 2001, 20, 4727-4733, and references therein.
33. For example, see: a) E. F. Archibong, A. J. Thakkar, Mol. Phys. 1994, 81, 557-567;
34. b) F. Ramondo, G. Portalone, M. Colapietro, L. Bencivenni, J. Mol. Struct. 1993, 302, 85-99;
35. c) P. von R. Schleyer, H. Jiao, N. J. R. van Eikema Hommes, V. G. Malkin, O. L. Malkina, J. Am. Chem. Soc. 1997, 119, 12669-12670;
36. d) E. Steiner, P. W. Fowler, R. W. A. Havenith, J. Phys. Chem. A 2002, 106, 7048-7056;
37. e) E. D. Jemmis, B. Kiran, Inorg. Chem. 1998, 37, 2110-2116;
38. f) S. Kawahara, S. Tsuzuki, T. Uchimaru, J. Chem. Phys. 2003, 119, 10081-10087.
39. a) W. Harshbarger, G. H. Lee, R. F. Porter, S. H. Bauer, J. Am. Chem. Soc. 1969, 91, 551-555;
40. b) W. Harshbarger, G. H. Lee, R. F. Porter, S. H. Bauer, Inorg. Chem. 1969, 8, 1683-1689;
41. c) R. Böse, A. H. Maulitz, P. Stellberg, Chem. Ber. 1994, 127, 1887-1889.
42. T. Franz, E. Hanecker, H. Nöth, W. Stöcker, W. Storch, G. Winter, Chem. Ber. 1986, 119, 900-916.
43. B. Thiele, P. Schreyer, U. Englert, P. Paetzold, R. Böse, B. Wrackmeyer, Chem. Ber. 1991, 124, 2209-2216.
44. J. Pipek, P. G. Mezey, J. Chem. Phys. 1989, 90, 4916-4926.
45. E. Steiner, P. W. Fowler, Phys. Chem. Chem. Phys. 2004, 6, 261-272.
46. J. H. van Lenthe, G. G. Balint-Kurti, J. Chem. Phys. 1983, 78, 5699-5713.
47. TURTLE, an ab initio VB/VBSCF program, J. Verbeek, J. H. Langenberg, C. P. Byrman, F. Dijkstra, J. J. Engelberts, J. H. van Lenthe, 1988-2004.
48. GAMESS-UK (2004) is a package of ab initio programs written by M. F. Guest, J. H. van Lenthe, J. Kendrick, K. Schoffel and P. Sherwood, with contributions from R. D. Amos, R. J. Buenker, H. J. J. van Dam, M. Dupuis, N. C. Handy, I. H. Hillier, P. J. Knowles, V. Bonacic-Koutecky, W. von Niessen, R. J. Harrison, A. P. Rendell, V. R. Saunders, A. J. Stone, D. J. Tozer and A. H. de Vries. The package is derived from the original GAMESS code: M. Dupuis, D. Spangler, J. Wendoloski, NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980.
49. B. H. Chirgwuin, C. A. Coulson, Proc. R. Soc. London 1950, A201, 196-209.
50. D. L. Cooper, S. C. Wright, J. Gerratt, P. A. Hyams, J. Chem. Soc., Perkin Trans. 2 1989, 6, 719-724.