Koopmans-based analysis of the optical spectra of p-phenylene-bridged intervalence radical ions

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9326-9333

  Nelsen, Stephen F ^a   Weaver, Michael N ^a   Telo, João P ^b   Lucht, Brett L ^c   Barlow, Stephen ^d  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c University of Rhode Island   (United States)

^d GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON ENERGY LEVELS; MATHEMATICAL MODELS; OXIDATION; PHASE TRANSITIONS; SPECTRUM ANALYSIS; STRUCTURE (COMPOSITION);

INTERVALENCE RADICAL IONS; KOOPMANS-BASED ANALYSIS; OPTICAL SPECTRA; SINGLY OCCUPIED ORBITAL (SOMO);

AROMATIC COMPOUNDS;

3 OXO 9 AZABICYCLO[3.3.1] DERIVATIVE; 4 PHENYLENE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; QUINONE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ENERGY; MODEL; MOLECULAR INTERACTION; OXIDATION; POLARIMETRY; SPECTROSCOPY; SPECTRUM; STRUCTURE ANALYSIS;

EID: 27744449808     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0514218     Document Type: Article

References (29)

1. Robin, M. B.; Day, P. Adv. Inorg. Chem. 1967, 10, 247-422.
2. Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391-444.
3. (a) Nelsen, S. F.; Ismagilov, R. F.; Powell, D. R. J. Am. Chem. Soc. 1996, 118, 6313-6314.
4. (b) Nelsen, S. F.; Ismagilov, R. F.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 10213-10222.
5. Nelsen, S. F.; Blackstock, S. C.; Yumibe, N. P.; Frigo, T. B.; Carpenter, J. E.; Weinhold, F. J. Am. Chem. Soc. 1985, 107, 143-149.
6. Nelsen, S. F.; Tran, H. Q.; Ismagilov, R. F.; Chen, L.-J.; Powell, D. R. J. Org. Chem. 1998, 63, 2536-2543.
7. Koopmans, T. Physica 1934, 1, 104-113.
8. Bally, T. In Radical Ionic Systems; Lund, A., Shiotani, M., Eds.; Kluwer: Dortrecht, The Netherlands, 1991; pp 3-54.
9. (a) Hoijtink, G. J.; Weijland, W. P. Recl. Trav. Chim. Pays-Bas 1957, 76, 836-838.
10. (b) Buschow, K. J. J.; Dieleman, J.; Hoijtink, G. J. Mol. Phys. 1963-1964, 7, 1-9.
11. The transition energies thus calculated include forbidden transitions that cannot be observed, so a way of estimating the oscillator strengths is needed, and was supplied by Clark for semiempirical calculations. See: Clark, T.; Teasley, M. F.; Nelsen, S. F.; Wynberg, H. J. Am. Chem. Soc. 1987, 709, 5719-5724.
12. Nelsen, S. F.; Konradsson, A. E.; Telo, J. P. J. Am. Chem. Soc. 2005, 127, 920-925.
13. Spartan'02, Wavefunction, Inc.: Irvine, CA, 2002.
14. (a) Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO, version 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001.
15. (b) We used the implementation in Gaussian, which is available at Wisconsin; the NBO provided with Gaussian is an older version that does not include the DIMO keyword.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
17. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
18. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
19. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
20. (d) Vosko, S. H.; Wilk, S. H.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
21. Nelsen, S. F.; Tran, H. Q. J. Phys. Chem. A 1999, 103, 8139-8144.
22. Bailey, S. E.; Zink, J. I.; Nelsen, S. F. J. Am. Chem. Soc. 2003, 125, 5939-5947.
23. Escobar, M.; Jin, Z.; Lucht, B. L. Org. Lett. 2002, 4, 2213-2216.
24. Risko, C.; Barlow, S.; Coropceanu, V.; Halik, M.; Brédas, J.-L.; Marder, S. R. Chem. Commun. 2003, 194-195.
25. Nelsen, S. F.; Weaver, M. N.; Telo, J. P.; Zink, J. I. J. Am. Chem. Soc. 2005, 127, 10611-10622.
26. Nelsen, S. F.; Luo, Y.; Weaver, M. N.; Lockard, J. V.; Zink, J. I. Beyond the Two-State model: Optical Spectra of Protected Diamine Intervalence Radical Cations Related to N,N,N′,N′-Tetraalkylbenzidine; under review.
27. Nelsen, S. F.; Konradsson, A. E.; Weaver, M. N.; Telo, J. P. J. Am. Chem. Soc. 2003, 125, 12493-12501.
28. This point will be presented in full in a future paper on quinone radical anions.
29. Maki, A. H. J. Chem. Phys. 1961, 35, 761.