Intramolecular electron transfer between doubly four σ-bond-linked tetraalkylhydrazine cationic and neutral units

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6863-6872

  Nelsen, Stephen F ^a   Ramm, Michael T ^a   Wolff, J Jens ^a   Powell, Douglas R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYL 3 ISOPROPYL 2,3 DIAZABICYCLO[2.2.2]OCTYLHYDRAZINE; CATION; DICHLOROMETHANE; HYDRAZINE DERIVATIVE; N,N' BIS 2,3 DIAZABICYCLO[2.2.2]OCTYLHYDRAZINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIC POTENTIOMETRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENERGY; SIMULATION; TEMPERATURE; THEORY; THERMODYNAMICS;

EID: 0030759794     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963415m     Document Type: Article

References (34)

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2. (a) Nelsen, S. F.; Chang, H.; Wolff, J. J.; Adamus, J. J. Am. Chem. Soc. 1993, 775, 12276.
3. + in chloroform, but not for solvents between AN and MC in polarity, and we assume here that ion pairing effects are negligible for these compounds in this solvent polarity range.
4. ESR for the t-Bu, Me compounds. See: Chang, H. Ph.D. Thesis, University of Wisconsin, 1992.
5. Nelsen, S. F.; Wolff, J. J.; Chang, H.; Powell, D, R. J. Am. Chem. Soc. 1991, 113, 7882.
6. Hush, N. S. Coord. Chem. Rev. 1985, 64, 135.
7. Nelsen, S. F.; Adamus, J.; Wolff, J. J. J. Am. Chem. Soc. 1994, 116, 1589.
8. For ET theory reviews, see: (a) Sutin, N. Prog. Inorg. Chem. 1983, 30, 441. (b) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
9. For ET theory reviews, see: (a) Sutin, N. Prog. Inorg. Chem. 1983, 30, 441. (b) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
10. Nelsen, S. F. J. Am. Chem. Soc. 1996, 118, 2047.
11. (a) Nelsen, S. F.; Chen, L.-J.; Petillo, P. A.; Evans, D. H.; Neugebauer, F. A. J. Am. Chem. Soc. 1993, 115, 10611.
12. (b) Nelsen, S. F.; Chen, L.-J.; Powell, D. R.; Neugebauer, F. A. J. Am. Chem. Soc. 1995, 117, 11434.
13. Nelsen, S. F.; Ramm, M. T.; Wolff, J. J.; Powell, D. R. J. Org. Chem. 1996, 61, 6313.
14. + compounds studied, more fits to eq 4, and all of the ESR simulations overlaid upon the experimental ESR spectra, see: Ramm, M. T. Ph.D. Thesis, University of Wisconsin, 1996.
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19. 4 We have not seen an application of eq 1 to experimental data using any value other than α = 1.
20. Nelsen, S. F.; Blackstock, S. C.; Haller, K. J. Tetrahedron 1986, 42, 6101.
21. bC twist angles of 179.7° and 179.4° at the inner N-i-Pr nitrogens and 57.8° and 54.6° at the outer N-t-Bu nitrogens. For the less-twisted aBIH, these numbers are 177.0° and 177.0° (inner N-i-Pr) and 62.7° and 62.9° (outer N-t-Bu).
22. Nelsen, S. F.; Trieber, D. A., II; Wolff, J. J.; Powell, D. R.; Rogers-Crowley, S. J. Am. Chem. Soc. 1997, 119, 6873.
23. (a) Shepard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328.
24. (b) Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395.
25. 4,19 and it is obvious that AM1 calculations may not be reliable for estimates of V.
26. v approaches zero, but continues to rise.
27. 2 but Y calculated using eq 3 increases more than enough to compensate for this. We shall discuss temperature effects on the optical spectra of organic intervalence compounds separately.
28. For example, see: ref 12 (paragraph 3, section 5). (a) Zeng, Y.; Zimmt, M. B. J. Phys. Chem. 1992, 96, 8395. (b) Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148 (see p 13157).
29. For example, see: ref 12 (paragraph 3, section 5). (a) Zeng, Y.; Zimmt, M. B. J. Phys. Chem. 1992, 96, 8395. (b) Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148 (see p 13157).
30. Data collection: SMART Software Reference Manual (1994). Data reduction: SAINT version 4 Software Reference Manual (1995). Solution, refinement, and graphics: G. M. Sheldreick (1994), SHELXTL version 5 Reference Manual, all from Siemens Analytical X-ray Instruments, 6300 Enterprise Dr., Madison, WI 53719-1173. Neutral atom scattering factors were taken from International Tables for Crystallography; Kluwer: Boston, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2.
31. Data collection: SMART Software Reference Manual (1994). Data reduction: SAINT version 4 Software Reference Manual (1995). Solution, refinement, and graphics: G. M. Sheldreick (1994), SHELXTL version 5 Reference Manual, all from Siemens Analytical X-ray Instruments, 6300 Enterprise Dr., Madison, WI 53719-1173. Neutral atom scattering factors were taken from International Tables for Crystallography; Kluwer: Boston, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2.
32. Data collection: SMART Software Reference Manual (1994). Data reduction: SAINT version 4 Software Reference Manual (1995). Solution, refinement, and graphics: G. M. Sheldreick (1994), SHELXTL version 5 Reference Manual, all from Siemens Analytical X-ray Instruments, 6300 Enterprise Dr., Madison, WI 53719-1173. Neutral atom scattering factors were taken from International Tables for Crystallography; Kluwer: Boston, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2.
33. Data collection: SMART Software Reference Manual (1994). Data reduction: SAINT version 4 Software Reference Manual (1995). Solution, refinement, and graphics: G. M. Sheldreick (1994), SHELXTL version 5 Reference Manual, all from Siemens Analytical X-ray Instruments, 6300 Enterprise Dr., Madison, WI 53719-1173. Neutral atom scattering factors were taken from International Tables for Crystallography; Kluwer: Boston, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2.
34. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.