Electrostatic attraction of counterion dominates the cation-π interaction of acetylcholine and tetramethylammonium with aromatics in chloroform [8]

Journal of the American Chemical Society

Volumn 121, Issue 50, 1999, Pages 11908-11909

  Bartoli, Sandra ^a   Roelens, Stefano ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINE; AROMATIC COMPOUND; CATION; CHLOROFORM; QUATERNARY AMMONIUM DERIVATIVE; TETRAMETHYLAMMONIUM;

BINDING AFFINITY; CHEMICAL STRUCTURE; LETTER; LIPOPHILICITY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY;

EID: 0033596311     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992415u     Document Type: Letter

References (21)

1. Ma, J. C.; Dougherty, D. A. Chem Rev. 1997, 97, 1303.
2. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558.
3. Roelens, S.; Torriti, R. J. Am. Chem. Soc. 1998, 120, 12443.
4. The only exception concerns the effect of the anion on complexation of quaternary ammonium cations exerted through hydrogen bonding to the host: Jeong, K.-S.; Hahn, K.-M.; Cho, Y. L. Tetrahedron Lett. 1998, 39, 3779.
5. (a) Lehn, J.-M.; Méric, R.; Vigneron, J. P.; Cesario, M.; Guilhem, J.; Pascard, C.; Asfari, Z.; Vicens, J. Supramol. Chem. 1995, 5, 97.
6. (b) Méric, R.; Vigneron, J. P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 129.
7. (c) Dhaenens, M.; Lacombe, L.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Chem. Commun. 1984, 1097.
8. (d) Harrowfield, J. M.; Ogden, M. I.; Richmond, W. R.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 2 1993, 2183.
9. (e) Schneider, H.-J.; Güttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449.
10. (a) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russel, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192.
11. (b) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359.
12. Price, E. In The Chemistry of nonaqueous solvents; Lagowski, J. J., Ed.; Academic Press: New York, 1966; Vol. 1, p 67.
13. The experimental technique and the precision achieved have been described in detail: Roelens, S.; Torriti, R. Supramol. Chem. 1999, 10, 225.
14. 3.
15. In the presence of active participation of the anion, inhibition of cation complexation caused by the anion binding to the host was observed in the association of alkylammonium salts to a macrocyclic phosphine oxide disulfoxide: Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. We thank a reviewer for calling our attention to this work.
16. Known theories are concerned with interactions within the ion-pair. See, for example: Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley-Interscience: New York, 1974.
17. See Supporting Information.
18. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, 1988; p 27.
19. See, for example: Altmann, R.; Jurkschat, K.; Schürmann, M.; Dakternieks, D.; Duthie, A. Organometallics 1998, 17, 5858.
20. Grunwald, E.; Highsmith, S.; I. T.-P., In Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley-Interscience: New York, 1974; Vol. 2, p 447.
21. In contrast, the variation in cation-π binding energy for a series of aromatics binding to the sodium cation is due to the electrostatic component of the binding. See: Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307.