Stabilization of p-phenylenebis(N-tert-butylaminoxyl) relative to p-benzoquinone-diimine N,N'-dioxide

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1550-1552

  Nakazono, Shuichi ^a   Karasawa, Satoru ^a   Koga, Noboru ^a   Iwamura, Hiizu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Aminoxyls; Aromaticity; Magnetic properties; Quinonediimines; Radicals

Indexed keywords

EID: 0032546943     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1550::AID-ANIE1550>3.0.CO;2-V     Document Type: Article

References (24)

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7. F. Kanno, K. Inoue, N. Koga, H. Iwamura, J. Am. Chem. Soc. 1993, 115, 847-850.
8. M. Dvolaitzky, R. Chiarelli, A. Rassat, Angew. Chem. 1992, 104, 220-222; Angew. Chem. Int. Ed. Engl. 1992, 31, 180-181.
9. M. Dvolaitzky, R. Chiarelli, A. Rassat, Angew. Chem. 1992, 104, 220-222; Angew. Chem. Int. Ed. Engl. 1992, 31, 180-181.
10. S. Fang, M.-S. Lee, D. A. Hrovat, W. T. Borden, J. Am. Chem. Soc. 1995, 117, 6727-6731.
11. For singlet m-phenylenebis(10-phenothiazinyl cation), see K. Okada, T. Imakura, M. Oda, H. Murai, M. Baumgarten, J. Am. Chem. Soc. 1996, 118, 3047-3048.
12. For singlet 2,6-pyridinediylbis(trimethylenemethane), see A. P. West, Jr., S. K. Silverman, D. A. Dougherty, J. Am. Chem. Soc. 1996, 118, 1452-1463
13. Shortening of the C-N bond is reported in α-nitrodiphenylmethane, which is in equiliblium with the aci-nitro tautomer: H. Bock, R. Dienelt, H. Schodel, Z. Havlas, E. Herdtweck, W. A. Herrmann, Angew. Chem. 1993, 105, 1826-1828; Angew. Chem. Int. Ed. Engl. 1993, 52, 1758-1760.
14. Shortening of the C-N bond is reported in α-nitrodiphenylmethane, which is in equiliblium with the aci-nitro tautomer: H. Bock, R. Dienelt, H. Schodel, Z. Havlas, E. Herdtweck, W. A. Herrmann, Angew. Chem. 1993, 105, 1826-1828; Angew. Chem. Int. Ed. Engl. 1993, 52, 1758-1760.
15. B. Bleaney, D. K. Bowers, Proc. R. Soc. London A 1952, 214, 451-465.
16. -1 more stable than a triplet ground state in solid state: R. Chiarelli, S. Gambarelli, A. Rassat, Mol. Cryst. Liq. Cryst. 1997, 108, 455-478.
17. Analogous p-benzoquinonediimine N,N′-dioxide derivatives prepared by oxidation of the corresponding amines and imines with perbenzoic acid have been reported: a) C. J. Pedersen, J. Am. Chem. Soc. 1957, 79, 2295-2299; b) A. R. Forrester, R. H. Thomson, G. R. Luckhurst, J.Chem. Soc. B 1968, 1311-1315.
18. Analogous p-benzoquinonediimine N,N′-dioxide derivatives prepared by oxidation of the corresponding amines and imines with perbenzoic acid have been reported: a) C. J. Pedersen, J. Am. Chem. Soc. 1957, 79, 2295-2299; b) A. R. Forrester, R. H. Thomson, G. R. Luckhurst, J.Chem. Soc. B 1968, 1311-1315.
19. a) E. Müller, E. Hertel, Liebigs Ann. Chem. 1944, 555, 157-186;
20. b) E. Müller, H. Neuhoff, Ber. 1939, 72, 2063-2075. Recently Rebmann et al. reported that triplet states can be populated thermally in paraextended bisaroxyls when the intervening p-phenylene ring is sterically distorted out of π conjugation with the two terminal aroxyl groups: A. Rebmann, J. Zhou, P. Schuler, A, Rieker, H. R. Stegmann, J. Chem. Soc. Perkin Trans. 2 1997, 1615-1617.
21. b) E. Müller, H. Neuhoff, Ber. 1939, 72, 2063-2075. Recently Rebmann et al. reported that triplet states can be populated thermally in paraextended bisaroxyls when the intervening p-phenylene ring is sterically distorted out of π conjugation with the two terminal aroxyl groups: A. Rebmann, J. Zhou, P. Schuler, A, Rieker, H. R. Stegmann, J. Chem. Soc. Perkin Trans. 2 1997, 1615-1617.
22. S. Nakazono, N. Koga, H. Iwamura, unpublished results.
23. H. Bock, C. Arad, C. N ther, I. G bel, A. John, Z. Naturforsch, B 1996, 51, 1391-1399.
24. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101 233. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).