A triphenylamine derivative with three p-(N-tert-butyl-N-oxylamino)phenyl radical units and yet a doublet ground state

Angewandte Chemie - International Edition

Volumn 38, Issue 12, 1999, Pages 1791-1793

  Itoh, Tetsuji ^a   Matsuda, Kenji ^a   Iwamura, Hiizu ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b National Institution for Academic Degrees and University Evaluation Tokyo   (Japan)

Author keywords

Ab initio calculations; Isoelectronic analogues; Magnetic properties; Radicals; Superexchange mechanism

Indexed keywords

AMINE; FERROMAGNETIC MATERIAL; NITROGEN DERIVATIVE; RADICAL; TRIS[4 (N TERT BUTYL N HYDROXYAMINO)PHENYL]AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; ELECTRON SPIN RESONANCE; MAGNETISM; MOLECULAR INTERACTION; MOLECULAR MODEL; SYNTHESIS;

EID: 0033553813     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990614)38:12<1791::AID-ANIE1791>3.0.CO;2-5     Document Type: Article

References (24)

1. For reviews see: a) H, Iwamura, Adv. Phys. Org. Chem. 1990, 26, 179-253;
2. b) D. A. Dougherty, Acc. Chem. Res. 1991, 24, 88-94;
3. c) H. Iwamura, N. Koga, Acc. Chem. Res. 1993, 26, 346-351;
4. d) J. S. Miller, A. J. Epstein, Angew. Chem. 1994, 106, 399-432;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 385-415;
6. e) A. Rajac, Chem. Rev. 1994, 94, 871-893;
7. f) O. Kahn, Molecular Magnetism, VCH, New York, 1993;
8. g) O. Kahn, Adv. Inorg. Chem. 1995, 43, 179-259;
9. h) K. S. Murray, Adv. Inorg. Chem. 1995, 43, 261-358.
10. D. C. Oniciu, K. Matsuda, H. Iwamura, J. Chem. Soc. Perkin Trans. 2 1996, 907-913.
11. For example see: a) D. Feller, W. T. Borden, E. Davidson, J. Chem. Phys. 1981, 74, 2256-2259;
12. b) D. R. Yarkony, H. F. Schaefer III, J. Am. Chem. Soc. 1974, 96, 3754-3758;
13. c) R. J. Crawford, D. M. Cameron, J. Am. Chem. Soc. 1966, 88, 2589-2590;
14. d) H. H. Greenwood, Trans. Faraday Soc. 1952 48, 677-679;
15. e) H. C. Longuet-Higgins, J. Chem. Phys. 1950, 18, 265-274.
16. W=0.054 for 2461 observed reflections (I> 3.00σ(I)) and 335 parameters. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101263. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
17. Symmetry operation: x, -y, 1/2+z.
18. The origin of the ferromagnetic interaction between the neighboring molelucles in crystals may be located at O1-C12′ and O3-C25′ (3.272(4) and 3.131(3) Å, respectively) along the chain made by the molecules aligned in the direction of the c axis.
19. T. Nakamura, T. Momose, T. Shida, K. Sato, S. Nakazawa, T. Kinoshita, T. Takui, K. Itoh, T. Okuno, A. Izuoka, T. Sugawara, J. Am. Chem. Soc. 1996, 118, 8684-8697;
20. K. Matsuda, T. Yamagata, T. Seta, H. Iwamura, K. Hori, J. Am. Chem. Soc. 1997, 119, 8058-8064.
21. [9, 10] However, compared with the carbon analogue 1, where two p-phenylene rings exhibit quinonoidal bond alternations of 0.05 Å, any bond alternation is less than 0.02 Å in 2. The dihedral angles between the benzene rings and the central trigonal nitrogen plane are somewhat larger for a quinonoid structure.
22. a) F. Kanno, K. Inoue, N. Koga, H. Iwamura, J. Am. Chem. Soc. 1993, 115, 847-850;
23. b) F. Kanno, K. Inoue, N. Koga, H. Iwamura, J. Phys. Chem. 1993, 97, 13 267-13 272.
24. A. W. Hanson, Acta Crystallogr. 1953, 6, 32-34.