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Volumn 44, Issue 16, 2005, Pages 2433-2437

In-plane bishomoaromaticity in tetranitrogen dianions: Solid-state, solution, and electronic structures

Author keywords

Bisdiazenes; Dianions; Heterocycles; Homoaromaticity; Quantum chemical calculations

Indexed keywords

CHEMICAL BONDS; DIMERS; ELECTRONIC STRUCTURE; NEGATIVE IONS; QUANTUM THEORY; REDUCTION; SODIUM; SOLUTIONS;

EID: 18044380917     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462126     Document Type: Article
Times cited : (6)

References (38)
  • 2
    • 0032479753 scopus 로고    scopus 로고
    • a) K. Exner, D. Hunkler, G. Gescheidt, H. Prinzbach, Angew. Chem. 1998, 110, 2013; Angew. Chem. Int. Ed. 1998, 37, 1910;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1910
  • 8
    • 18044396864 scopus 로고    scopus 로고
    • note
    • 3, Z = 1. The structure could be solved unequivocally but due to the low scattering power of the crystals no satisfying refinement was possible.
  • 9
    • 18044392188 scopus 로고    scopus 로고
    • unpublished
    • 2 [B3LYP/6-31 + G(d,p)]. Attempts to crystallize the latter have not been successful (J. Geier, unpublished).
    • Geier, J.1
  • 14
    • 0345491105 scopus 로고
    • b) C. Lee, W. Yang, R. G. Parr. Phys. Rev. B 1988, 37, 785. Other density functionals (B3PW91, BLYP, BPW91) produced significantly larger deviations from the solid-state structure.
    • (1988) Phys. Rev. B , vol.37 , pp. 785
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 15
    • 40749094858 scopus 로고
    • GIAO-B3LYP/6-31+G(d,p). a) R. Ditchfield, Mol. Phys. 1974, 27, 789; b) K. Wolinski, J. F. Hilton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251.
    • (1974) Mol. Phys. , vol.27 , pp. 789
    • Ditchfield, R.1
  • 21
    • 18044393543 scopus 로고    scopus 로고
    • note
    • -0.
  • 24
    • 0345401784 scopus 로고
    • c) Review: R. F. W. Bader, Chem. Rev. 1991, 91, 893. The calculations were performed with the program AIM2000, version 2.0: F. Biegler-König, J. Schönbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545; http://gauss.fh- bielefeld.de/aim2000.
    • (1991) Chem. Rev. , vol.91 , pp. 893
    • Bader, R.F.W.1
  • 25
    • 0035871851 scopus 로고    scopus 로고
    • c) Review: R. F. W. Bader, Chem. Rev. 1991, 91, 893. The calculations were performed with the program AIM2000, version 2.0: F. Biegler-König, J. Schönbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545; http://gauss.fh- bielefeld.de/aim2000.
    • (2001) J. Comput. Chem. , vol.22 , pp. 545
    • Biegler-König, F.1    Schönbohm, J.2    Bayles, D.3
  • 30
    • 0037473036 scopus 로고    scopus 로고
    • [7,8,14,15] This species does not have a bond critical point between these particular carbon atoms, a phenomenon that was termed "no bond homoaromaticity": a) K. J. Szabo, E. Kraka, D. Cremer, J. Org. Chem. 1996, 61, 2788. Other applications of the topological analysis of the electron density to potentially homoconjugated systems are described in: b) N. H. Werstiuk, Y.-G. Wang, J. Phys. Chem. A 2003, 107, 9434. For the application of the electron localization function see: c) C. Lepetit, B. Silvi, R. Chauvin, J. Phys. Chem. A 2003, 107, 464.
    • (1996) J. Org. Chem. , vol.61 , pp. 2788
    • Szabo, K.J.1    Kraka, E.2    Cremer, D.3
  • 31
    • 0242708937 scopus 로고    scopus 로고
    • [7,8,14,15] This species does not have a bond critical point between these particular carbon atoms, a phenomenon that was termed "no bond homoaromaticity": a) K. J. Szabo, E. Kraka, D. Cremer, J. Org. Chem. 1996, 61, 2788. Other applications of the topological analysis of the electron density to potentially homoconjugated systems are described in: b) N. H. Werstiuk, Y.-G. Wang, J. Phys. Chem. A 2003, 107, 9434. For the application of the electron localization function see: c) C. Lepetit, B. Silvi, R. Chauvin, J. Phys. Chem. A 2003, 107, 464.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 9434
    • Werstiuk, N.H.1    Wang, Y.-G.2
  • 32
    • 0037473036 scopus 로고    scopus 로고
    • [7,8,14,15] This species does not have a bond critical point between these particular carbon atoms, a phenomenon that was termed "no bond homoaromaticity": a) K. J. Szabo, E. Kraka, D. Cremer, J. Org. Chem. 1996, 61, 2788. Other applications of the topological analysis of the electron density to potentially homoconjugated systems are described in: b) N. H. Werstiuk, Y.-G. Wang, J. Phys. Chem. A 2003, 107, 9434. For the application of the electron localization function see: c) C. Lepetit, B. Silvi, R. Chauvin, J. Phys. Chem. A 2003, 107, 464.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 464
    • Lepetit, C.1    Silvi, B.2    Chauvin, R.3
  • 34
    • 0001597180 scopus 로고    scopus 로고
    • For the cyclic dimer of the tetracyanoethylene radical anion (4 C/ 6e) chemical bonds over C-C distances of 2.9 Å were formulated: a) J. J. Novoa, P. Lafuente, E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608; Angew. Chem. Int. Ed. 2001, 40, 2540; b) R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894; c) J.-M. Lü, S. V. Rosokha, J. K. Koch, J. Am. Chem. Soc. 2003, 125, 12 161; d) Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008.
    • (2001) Angew. Chem. , vol.113 , pp. 2608
    • Novoa, J.J.1    Lafuente, P.2    Del Sesto, E.3    Miller, J.S.4
  • 35
    • 0035796428 scopus 로고    scopus 로고
    • For the cyclic dimer of the tetracyanoethylene radical anion (4 C/ 6e) chemical bonds over C-C distances of 2.9 Å were formulated: a) J. J. Novoa, P. Lafuente, E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608; Angew. Chem. Int. Ed. 2001, 40, 2540; b) R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894; c) J.-M. Lü, S. V. Rosokha, J. K. Koch, J. Am. Chem. Soc. 2003, 125, 12 161; d) Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2540
  • 36
    • 0037021030 scopus 로고    scopus 로고
    • For the cyclic dimer of the tetracyanoethylene radical anion (4 C/ 6e) chemical bonds over C-C distances of 2.9 Å were formulated: a) J. J. Novoa, P. Lafuente, E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608; Angew. Chem. Int. Ed. 2001, 40, 2540; b) R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894; c) J.-M. Lü, S. V. Rosokha, J. K. Koch, J. Am. Chem. Soc. 2003, 125, 12 161; d) Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008.
    • (2002) Chem. Eur. J. , vol.8 , pp. 4894
    • Del Sesto, R.E.1    Miller, J.S.2    Lafuente, P.3    Novoa, J.J.4
  • 37
    • 0141923194 scopus 로고    scopus 로고
    • For the cyclic dimer of the tetracyanoethylene radical anion (4 C/ 6e) chemical bonds over C-C distances of 2.9 Å were formulated: a) J. J. Novoa, P. Lafuente, E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608; Angew. Chem. Int. Ed. 2001, 40, 2540; b) R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894; c) J.-M. Lü, S. V. Rosokha, J. K. Koch, J. Am. Chem. Soc. 2003, 125, 12 161; d) Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12161
    • Lü, J.-M.1    Rosokha, S.V.2    Koch, J.K.3
  • 38
    • 2942583138 scopus 로고    scopus 로고
    • For the cyclic dimer of the tetracyanoethylene radical anion (4 C/ 6e) chemical bonds over C-C distances of 2.9 Å were formulated: a) J. J. Novoa, P. Lafuente, E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608; Angew. Chem. Int. Ed. 2001, 40, 2540; b) R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J. 2002, 8, 4894; c) J.-M. Lü, S. V. Rosokha, J. K. Koch, J. Am. Chem. Soc. 2003, 125, 12 161; d) Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008.
    • (2004) Phys. Chem. Chem. Phys. , vol.6 , pp. 2008
    • Jung, Y.1    Head-Gordon, M.2


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