Modulating spin delocalization in conjugated nitroxides: 2-(N-aminoxyl-N-tert-butyl)-benzothiazole

Tetrahedron Letters

Volumn 45, Issue 33, 2004, Pages 6295-6298

  Taylor, Patrick ^a   Ghalsasi, Prasanna ^a   Lahti, Paul ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Nitroxides; Radicals; Spin delocalization; Spin density

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; HYDROXYLAMINE; NITROXIDE;

ARTICLE; ELECTRON SPIN RESONANCE; MATHEMATICAL ANALYSIS; MATHEMATICAL MODEL; OXIDATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 3242809609     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.084     Document Type: Article

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19. Computations were carried using Gaussian03, Revision B03 on an SGI computer, by Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian: Pittsburgh, PA, 2003. The hybrid UB3LYP density functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) was used with the cc-pVDZ basis set for the final spin density computations (Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358)
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21. Computations were carried using Gaussian03, Revision B03 on an SGI computer, by Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian: Pittsburgh, PA, 2003. The hybrid UB3LYP density functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648â€"5652) was used with the cc-pVDZ basis set for the final spin density computations (Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358)
22. X) is equal to a constant (Q) times the spin density (ρ) on the atom in question (or, for aryl hydrogens, the spin density on the attached π-carbon atom). For X = N, we used Q = 30 G, for X = aryl H we used Q = -22 G. Simulation of experimental spectra were carried out using WINSIM (Duling, D. R. J. Magn. Res. 1994, B104, 105)
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