Quantification of functional group interactions in transition states

Journal of the American Chemical Society

Volumn 125, Issue 33, 2003, Pages 9936-9937

  Hunter, Christopher A ^a   Low, Caroline M R ^b   Vinter, Jeremy G ^b   Zonta, Cristiano ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; METHYL IODIDE; PYRIDINE;

ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; COMPLEX FORMATION; HYDROGEN BOND; METHYLATION; MOLECULAR INTERACTION; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; TITRIMETRY;

EID: 0043022295     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034767d     Document Type: Article

References (18)

1. Kraut, J. Science 1988, 242, 533-540. Schramm, V. L. Curr. Opin. Chem. Biol. 2001, 5, 556-563. Bruice, T. C. Acc. Chem. Res. 2002, 35, 139-148.
2. Kraut, J. Science 1988, 242, 533-540. Schramm, V. L. Curr. Opin. Chem. Biol. 2001, 5, 556-563. Bruice, T. C. Acc. Chem. Res. 2002, 35, 139-148.
3. Kraut, J. Science 1988, 242, 533-540. Schramm, V. L. Curr. Opin. Chem. Biol. 2001, 5, 556-563. Bruice, T. C. Acc. Chem. Res. 2002, 35, 139-148.
4. Corey, M. J.; Corey, E. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 11428-11434.
5. Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544. Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. M.; Seward, E. M. Chem. Eur. J. 2002, 13, 2848-2859. Chessari, G.; Hunter, C. A.; Low, C. M. R.; Packer, M. J.; Vinter, J. G.; Zonta, C. Chem. Eur. J. 2002, 13, 2860-2867.
6. Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544. Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. M.; Seward, E. M. Chem. Eur. J. 2002, 13, 2848-2859. Chessari, G.; Hunter, C. A.; Low, C. M. R.; Packer, M. J.; Vinter, J. G.; Zonta, C. Chem. Eur. J. 2002, 13, 2860-2867.
7. Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544. Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. M.; Seward, E. M. Chem. Eur. J. 2002, 13, 2848-2859. Chessari, G.; Hunter, C. A.; Low, C. M. R.; Packer, M. J.; Vinter, J. G.; Zonta, C. Chem. Eur. J. 2002, 13, 2860-2867.
8. Hunter, C. A.; Low, C. M. R.; Rotger, C.; Vinter, J. G.; Zonta, C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4873-4876.
9. Stauffer, D. A.; Barrans, R. E., Jr.; Dougherty, D. A Angew. Chem., Int. Ed. Engl. 1990, 29, 915-918. McCurdy, A.; Jimenez, L.; Stauffer, D. A.; Dougherty, D. A. J. Am. Chem. Soc. 1992, 114, 10314-10321. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1996, 61, 4355-4360.
10. Stauffer, D. A.; Barrans, R. E., Jr.; Dougherty, D. A Angew. Chem., Int. Ed. Engl. 1990, 29, 915-918. McCurdy, A.; Jimenez, L.; Stauffer, D. A.; Dougherty, D. A. J. Am. Chem. Soc. 1992, 114, 10314-10321. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1996, 61, 4355-4360.
11. Stauffer, D. A.; Barrans, R. E., Jr.; Dougherty, D. A Angew. Chem., Int. Ed. Engl. 1990, 29, 915-918. McCurdy, A.; Jimenez, L.; Stauffer, D. A.; Dougherty, D. A. J. Am. Chem. Soc. 1992, 114, 10314-10321. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1996, 61, 4355-4360.
12. obst.
13. D, and thus it is possible to dissect out the thermodynamic contribution of the interaction of the transition state with the aromatic ring from all of the other interactions involved in Complex A.
14. Fabbrizzi, L.; Gatti, F.; Pallavicini, P.; Zambarbieri, E. Chem. Eur. J. 1999, 5, 682-690.
15. Due to the poor solubility of the iodide salts, it was not possible to perform the NMR titrations with the iodide product. However, we have shown that changing the anion has a negligible effect on the interaction energy; therefore, the hexafluorophosphate results should be representative of the behavior of the reaction products. Hunter, C. A.; Low, C. M. R.; Rotger, C.; Vinter, J. G.; Zonta, C. Chem. Commun. 2003, 834-835.
16. Arnett, E. M.; Reich, R. J. Am. Chem. Soc. 1980, 102, 5892-5902.
17. Smith, P. J.; Soose, D. J.; Wilcox, C. S. J. Am. Chem. Soc. Soc. 1991, 113, 7412-7414.
18. Fong, T. M.; Cascieri, M. A.; Yu, H.; Bansal, A.; Swain, C.; Strader, C. D. Nature 1993, 362, 350-353.