Intramolecular kinetic isotope effect in hydride transfer from dihydroacridine to a quinolinium ion. Rejection of a proposed two-step mechanism with a kinetically significant intermediate

Organic and Biomolecular Chemistry

Volumn 6, Issue 18, 2008, Pages 3349-3353

  Perrin, Charles L ^a   Zhao, Chen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER MOBILITY;

HYDRIDE TRANSFERS; KINETIC ISOTOPE EFFECT; TWO-STEP MECHANISMS;

ISOTOPES;

ACRIDINE DERIVATIVE; HYDROGEN; ION; ISOTOPE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACRIDINES; HYDROGEN; IONS; ISOTOPES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; QUINOLINIUM COMPOUNDS;

EID: 52649099034     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b806869k     Document Type: Article

References (32)

1. V. D. Parker Pure Appl. Chem. 2005 77 1823 1833
2. Y. Lu K. L. Handoo V. D. Parker Org. Biomol. Chem. 2003 1 36 38
3. K. L. Handoo Y. Lu Y. Zhao V. D. Parker Org. Biomol. Chem. 2003 1 24 26
4. K. L. Handoo Y. Lu Y. Zhao V. D. Parker J. Am. Chem. Soc. 2003 125 9381 9387
5. V. D. Parker Y. Zhao Y. Lu G. Zheng J. Am. Chem. Soc. 1998 120 12720 12727
6. K. L. Handoo J. P. Cheng V. D. Parker J. Chem. Soc., Perkin Trans. 2 2001 1476 1480
7. V. D. Parker J. Phys. Org. Chem. 2006 19 714 724
8. W. F. Hao V. D. Parker J. Org. Chem. 2008 73 48 55
9. Y. Lu Y. X. Zhao V. D. Parker J. Am. Chem. Soc. 2001 123 5900 5907
10. Y. X. Zhao Y. Lu V. D. Parker J. Chem. Soc., Perkin Trans. 2 2001 1481 1488
11. Y. X. Zhao Y. Lu V. D. Parker J. Am. Chem. Soc. 2001 123 1579 1586
12. E. Humeres T. W. Bentley Org. Biomol. Chem. 2003 1 1969 1971
13. V. D. Parker Y. Lu Org. Biomol. Chem. 2003 1 2621 2623
14. X. Q. Zhu J. Y. Zhang J.-P. Cheng J. Org. Chem. 2006 71 7007 7015
15. K. J. Stanger J. J. Lee B. D. Smith J. Org. Chem. 2007 72 9663 9668
16. D. Ostovic R. M. G. Roberts M. M. Kreevoy J. Am. Chem. Soc. 1983 105 7629 7631
17. M. M. Kreevoy A. T. Kotchevar J. Am. Chem. Soc. 1990 112 3579 3583
18. I.-S. H. Lee E. H. Jeoung M. M. Kreevoy J. Am. Chem. Soc. 2001 123 7492 7496
19. Y. Lu Y. Zhao K. L. Handoo V. D. Parker Org. Biomol. Chem. 2003 1 173 181
20. M. Eigen Angew. Chem., Int. Ed. Engl. 1964 3 1 19
21. V. D. Kiselev J. G. Miller J. Am. Chem. Soc. 1975 97 4036 4039
22. B. K. Carpenter, Determination of Organic Reaction Mechanisms, Wiley-Interscience, New York, 1984, pp. 101-104
23. Z. Song P. Beak J. Am. Chem. Soc. 1990 112 8126 8134
24. E. Baciocchi A. Calcagni O. Lanzalunga J. Org. Chem. 2008 73 10.1021/jo8001672
25. S.-H. Dai W. R. Dolbier, Jr. J. Am. Chem. Soc. 1972 94 3946 3952
26. M. Marx T. T. Tidwell J. Org. Chem. 1984 49 788 93
27. L. M. Stephenson M. J. Grdina M. Orfanopoulos Acc. Chem. Res. 1980 13 419 125
28. E. Baciocchi A. Calcagni O. Lanzalunga J. Am. Chem. Soc. 1998 120 5783 5787
29. J. J. Steffens D. Chipman J. Am. Chem. Soc. 1971 93 6694 6696
30. D. M. Chipman R. Yaniv P. van Eikeren J. Am. Chem. Soc. 1980 102 3244 3246
31. L. C. Kurz C. Frieden J. Am. Chem. Soc. 1980 102 4198 4203
32. M. B. Goshe V. E. Anderson Anal. Biochem. 1995 231 387 392