Control of pyramidal inversion rates by redox switching

Journal of the American Chemical Society

Volumn 128, Issue 44, 2006, Pages 14260-14261

  Davies, Mark W ^a   Shipman, Michael ^a   Tucker, James H R ^c   Walsh, Tiffany R ^a,b  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHALENEDIOL; AZIRIDINE DERIVATIVE; HYDROXYL GROUP; NAPHTHALENE DERIVATIVE; NAPHTHOQUINONE; SODIUM DITHIONITE; UNCLASSIFIED DRUG; XYLENE;

ALKYLATION; ARTICLE; ENTHALPY; HYDROGEN BOND; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXIDATION REDUCTION REACTION; REDUCTION; SYNTHESIS;

EID: 33750681666     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065325f     Document Type: Article

References (25)

1. For definitions and recent examples of various redox-switched processes, see (a) Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
2. (b) Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
3. (c) Sporer, C.; Ratera, I.; Ruiz-Molina, D.; Zhao, Y. X.; Vidal-Gancedo, J.; Wurst, K.; Jaitner, P.; Clays, K.; Persoons, A.; Rovira, C.; Veciana, J. Angew. Chem., Int. Ed. 2004, 43, 5266-5268.
4. (d) Kihara, N.; Hashimoto, M.; Takata, T. Org. Lett. 2004, 6, 1693-1696.
5. (e) Gomar-Nadal, E.; Veciana, J.; Rovira, C.; Amabilino, D. B. Adv. Mater. 2005, 17, 2095-2098.
6. (f) van Dijk, E. H.; Myles, D. J. T.; van der Veen, M. H.; Hummelen, J. C. Org. Lett. 2006, 8, 2333-2336 and references therein.
7. For an example of redox-switched luminescence using the quinone/hydroquinone redox couple, see Goulle, V.; Harriman, A.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1034-1036.
8. (a) Tucker, J. H. R.; Collinson, S. R. Chem. Soc. Rev. 2002, 31, 147-156.
9. (b) Bu, J. J.; Lilienthal, N. D.; Woods, J. E.; Nohrden, C. E.; Hoang, K. T.; Truong, D.; Smith, D. K. J. Am. Chem. Soc. 2005, 127, 6423-6429 and references therein.
10. For an intramolecular example, see Boyd, A. S. F.; Carroll, J. B.; Cooke, G.; Garety, J. F.; Jordan, B. J.; Mabruk, S.; Rosair, G.; Rotello, V. M. Chem. Commun. 2005, 2468-2470.
11. For examples where rotary (360°) motion rates are affected by complexation, see Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281-1376.
12. For examples where shuttling rates in rotaxanes are controlled by external inputs, see (a) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093.
13. (b) Ghosh, P.; Federwisch, G.; Kogej, M.; Schalley, C. A.; Haase, D.; Saak, W.; Lutzen, A.; Gschwind, R. M. Org. Biomol. Chem. 2005, 3, 2691-2700 and references therein.
14. Jennings, W. B.; Boyd D. R. In Cyclic Organonitrogen Stereodynamics; Lambert, J. B., Takechi, Y., Eds.; VCH: Cambridge, U.K., 1992; pp 105-158.
15. Drakenberg, T.; Lehn, J.-M. J. Chem. Soc., Perkin Trans. 2 1972, 532-535.
16. The use of a trans-disubstituted aziridine results in the N-invertomers being identical (i.e., 1a = 1b; 2a = 2b), simplifying the data analysis.
17. The Chemistry of the Quinonoid Compounds; Patai, S. Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1987; Vol. 2.
18. Foglia, T. A.; Swern, D. J. Org. Chem. 1969, 34, 1680-1684.
19. Pfister, J. R. Synthesis 1984, 969-970.
20. Syper, L.; Kloc, K.; Mlochowski, J.; Szluc, Z. Synthesis 1979, 521-522.
21. Reich, H. J. J. Chem. Educ.: Software, Ser. D 1996, 3D.
22. Evidence for an intramolecular H-bond is provided by the fact that essentially no change in the chemical shift of the downfield OH in 2 was detected upon variation in sample concentration (δ 10.83 ppm, 0.021 M; δ 10.82 ppm, 0.006 M; δ 10.82, 0.001 M). Geometric constraints necessitate that the C-1-OH and not the C-4-OH is involved.
23. -1: Gromak, V. V. J. Mol. Struct.: THEOCHEM 2005, 726, 213-224.
24. Wu, X.; Vargas, M. C.; Nayak, S.; Lotrich, V.; Scoles, G. J. Chem. Phys. 2001, 115, 8748-8757.
25. Walsh, T. R. Phys. Chem. Chem. Phys. 2005, 7, 443-451.