Abstract
2-(2-pyridyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical 2 and the 2-[2-(N-alkyl)-pyrid-inium] derivatives (3a and 3b) were synthesized and characterized by elemental analysis, melting points, and spectroscopy. The density functional theory (DFT) was used in order to obtain the structures and electronic properties of the new nitronyl nitroxide radicals. Modified reaction procedures of the intermediates are described with better yield and purity of the final products. The magnetic properties of the compounds 2, 3a, and 3b are predicted for the first time using a simple model of charge transference, in the framework of the molecular orbital calculations. The obtained results show that the substituent at the central carbon atom of the imidazoline is important to determine the spin distribution and consequently the nature of the magnetic interaction.
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REFERENCES
Tamura, M. et al. Chem. Phys. Lett. 1991, 186, 401.
Caneschi, A.; Gatteschi, D.; Rey, P.; Sessoli, R. Inorg. Chem. 1988, 27, 1756. (b) Caneschi, A.; Gatteschi, D.; Sessoli, R.; Rey, P. Acc. Chem. Res. 1989, 22, 392.
Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447. (b) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Bergerat, P.; Kahn, O. J. Am. Chem. Soc. 1994, 116, 3866. (c) Stumpf, H. O.; Pei, Y.; Michaut, C.; Kahn, O.; Renard, J.-P.; Ouahab, L. Chem. Mater. 1994, 6, 257.
Humberto O. Stumpf. Ph.D. thesis, Université de Paris-Sud, Orsay, 1993. (b) Stumpf, H. O.; Pei, Y.; Kahn, O.; Sletten, J.; Renard, J. J. Am. Chem. Soc. 1993, 115, 6738.
Vaz, M. G. F.; Pinheiro, M. M. L.; Stumpf, H. O.; Alcântara, A. F. C.; Golhen, S.; Ouahab, L.; Cador, O.; Mathonière, C.; Kahn, O. Chem. Eur. J. 1999, 5, 1486.
Okuno, T.; Otsuka, T.; Awaga, K. J. Chem. Soc., Chem. Commun. 1995, 827.
Ueda, K.; Tsujii, M.; Suga, T.; Sugimoto, T.; Kanehisa, N.; Kai, Y.; Hosoito, N. Chem. Phys. Letters 1996, 253, 355.
Oshio, H.; Watanabe, T.; Ohto, A.; Ito, T.; Masuda, H. Inorg. Chem. 1996, 35, 472.
Awaga, K.; Yamaguchi, A.; Okuno, T. Mol. Cryst. Liq. Cryst. 1995, 271, 9.
Seigle, L. W.; Hass, H. B. J. Org. Chem. 1940, 5, 100.
Ralph Sayre. J. Am. Chem. Soc. 1955, 77, 6689.
Lamchen, M.; Mittag, T. W. J. Chem. Soc. (C) 1996, 2300.
Zheludev, A.; Barone, V.; Bonnet, M.; Delley, B.; Grand, A.; Ressouche, E.; Rey, P.; Subra, R.; Schweizer, J. J. Am. Chem. Soc. 1994, 116, 2019.
Yamanaka, S.; Kawakami, T.; Yamada, S.; Nagao, H.; Nakamo, M.; Yamaguchi, K. Chem. Phys. lett. 1995, 240, 268.
Öhrströn, L.; Grand, A.; Pilawa, B. Acta Chemica Scandinavica 1996, 50, 458.
Becke, A. D. Phys. Rev. A 1988, 38, 3098.
Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
Michlich, B.; Savin, A.; Stall, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
Ullman, E. F.; Osiecki, J. H.; Boocock, D. G. B.; Darey, R. J. Am. Chem. Soc. 1972, 94, 7049.
Alcântara, A. F. C.; Dos Santos, H. F.; Vaz, M. G. F.; Stumpf, H. O., De Almeida, W. B. In 21st Reunião Anual da Sociedade Brasileira de Química, Poços de Caldas, Brazil, Abstracts, vol. 1, 1998, p. 13.
Awaga, K. et al. Chem. Phys. Lett. 1987, 141, 540.
Awaga, K.; Maruyama, Y. J. Chem. Phys. 1989, 91, 2743.
Awaga, K.; Inabe, T.; Maruyama, Y. Chem. Phys. Lett. 1992, 190, 349.
Awaga, K.; Inabe, T.; Maruyama, Y. Chem. Phys. Lett. 1992, 195, 21.
Osiecki, J. H.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 1078.
Davis, M. S. et al. J. Am. Chem. Soc. 1972, 94, 5588.
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Alcântara, A.F.C., Dos Santos, H.F., De Almeida, W.B. et al. Synthesis and Properties of New 2-[2-(N-alkyl)-pyridinium]-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide Iodide Radicals. Structural Chemistry 10, 367–374 (1999). https://doi.org/10.1023/A:1022043527856
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DOI: https://doi.org/10.1023/A:1022043527856