Theoretical study of anion binding to calix[4]pyrrole: The effects of solvent, fluorine substitution, cosolute, and water traces

Journal of the American Chemical Society

Volumn 124, Issue 43, 2002, Pages 12796-12805

  Ramon Blas J ^a   Márquez, Manuel ^b,c   Sessler, Jonathan L ^d   Javier Luque, F ^a   Orozco, Modesto ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b LOS ALAMOS NATIONAL LABORATORY   (United States)

^c Kraft Inc   (United States)

^d UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; HYDRATION; INTEGRATION; MOLECULAR DYNAMICS; SUBSTITUTION REACTIONS;

APOLAR SOLVENTS;

NEGATIVE IONS;

ANION; CALIX[4]PYRROLE; FLUORINE; OCTAFLUOROCALIX[4]PYRROLE; PYRROLE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; BINDING AFFINITY; CALCULATION; CONFORMATION; ENERGY; FLUORINATION; GAS; HYDRATION; MOLECULAR DYNAMICS; QUANTUM MECHANICS; THEORETICAL STUDY; THERMODYNAMICS;

EID: 0037202186     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020318m     Document Type: Article

References (54)

1. Lange, L. G., III.; Riordan, J. F.; Vallèe, B. L. Biochemistry 1974, 13, 4361.
2. Lehn, J. M. Supramolecular Chemistry; VCH Press: Weinheim, Germany, 1995.
3. Desvergne, J. P.; Czarnik, A. W. Chemosensors of Ion and Molecular Recognition; NATO ASI Series C; Kluwer: Dordrecht, The Netherlands, 1997.
4. de Silva, A. P.; Guanaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
5. Bianchi, A.; Bowman-James, K.; García-España, E. Supramolecular Chemistry of Anions; Willey: New York, 1997.
6. Schmidtchen, F. P. Nachr. Chem., Tech. Lab. 1988, 36, 10.
7. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
8. Jorgensen, W. L. Chemtracts: Org. Chem. 1991, 4, 91.
9. Sessler, J. L.; Cyr, M.; Furata, H.; Kral, V.; Tody, T.; Morishima, T.; Shionoya, M.; Weghorn, S. Pure Appl. Chem. 1993, 65, 393.
10. Beer, P. D. Chem. Commun. 1996, 689.
11. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666.
12. Baeyer, A. Ber. Dtsch. Chem. Ges. 1866, 19, 214.
13. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140.
14. Gale, P. A.; Sessler, J. L.; Allen, W. E.; Tvermoes, N. A.; Lynch, V. Chem. Commun. 1997, 665.
15. Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1.
16. Sessler, J. L.; Gale, P. A.; Genge, J. W. Chem. - Eur. J. 1998, 4, 1095.
17. Anzenbacher, P.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350.
18. Sessler, J. L.; Anzenbacher, P.; Miyaji, H.; Jursíková, K.; Bleasdale, E. R.: Gale, P. A. Ind. Eng. Chem. Res. 2000, 39, 3471.
19. Sessler, J. L.: Anzenbacher, P.; Shriver, J. A.; Jursíková, K.; Lynch, V. M.; Marquez, M. J. Am. Chem. Soc. 2000, 122, 12061.
20. Anzenbacher, P.; Try, A. C.; Miyaji, H.; Jursíková, K.; Marquez, M.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 10268.
21. Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Intl. Ed. 2000, 39, 1777.
22. Miyaji, H.; Anzenbancher, P.; Sessler, J. L.; Blesdale, E. R.; Gale, P. A. Chem. Commun. 1999, 1723.
23. Turner, B.; Shterenberg, A.; Kapon, M.; Suwinska, K.; Eichen, Y. Chem. Commun. 2001, 13.
24. Anzenbacher, P.; Jursíková, K.; Lynch, V. M.; Gale, P. A.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 11020.
25. Bucher, C.; Zimmerman, R. S.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 2001, 123, 9716.
26. Schmidtchen, F. P. Org. Lett. 2002, 4, 431.
27. Wu, Y. D.; Wang, D. F.; Sessler, J. L. J. Org. Chem. 2001, 66, 3739.
28. Allen, W. E.; Gale, P. A.; Brown, C. T.; Lynch, V. M.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 12471.
29. Jacoby, D.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. J. Chem. Soc., Chem. Commun. 1991, 790.
30. Blas, J. R.; Luque, F. J.; Márquez, M.; Orozco, M. To be published.
31. van Hoorn, W. P.; Jorgensen, W. L. J. Org. Chem. 1999, 64, 7439.
32. Woods, C. J.; Camiolo, S.; Light, M. E.; Coles, S. J.; Hursthouse, M. B.; King, M. A.; Gale, P. A.; Essex, J. W. J. Am. Chem. Soc. 2002, 124, 8644.
33. Boys, S. F.; Bernardi, F. Mol. Phys. 1989, 214, 15.
34. Luque, F. J.; Orozco, M. J. Comput. Chem. 1998, 19, 866.
35. Cubero, E.; Luque, F. J.; Orozco, M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5976.
36. Lee, C., Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785.
37. Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. J. Phys. Chem. 1993, 97, 10269.
38. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179.
39. Jorgensen, W. L.; Tirado-Rives, J. J. Am. Chem. Soc. 1988, 110, 1657.
40. Guàrdia, E.; Pinzón, R.; Casulleras, J.; Orozco, M.; Luque, F. J. Mol. Simul. 2001, 26, 287.
41. - (2.32, 0.09). The radii used here are ∼0.2-0.3 Å shorter than those typically used to simulate halogens in aqueous solution (like the OPLS parameters). Energy calculations using standard OPLS parameters lead to a sizable underestimation of pyrrol-halogen interaction and to an overestimation of the halogen-pyrrol distance. Thus, classical calculations using the OPLS force field for halogens lead to a systematic underestimation of ∼4-6 kcal/mol in the stabilization energy of the halogen-pyrrol (or 3,4-difluoropyrrole) complex and to an overestimation of ∼0.3 Å of the equilibrium distance. Since the deviation between QM and OPLS values is similar for all halogens, the change of van der Waals radii does not have an impact in the relative free energy of binding of halogens but can be important for the description of the preferential binding of halogens relative to other ions such as the phosphate, which are described with van der Waals parameters which lead to an accurate description of the ion-pyrrole interaction (0.5 (pyrrole) and 0.9 (3,4-difiuoropyrrole) kcal/mol difference between classical and QM calculations).
42. Different authors have suggested that phosphate exists mostly as a dimer in solution (Chu, F.; Flatt, L. S.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 4194), but this implies the existence of a monoanionic complex, with one phosphate and one phosphoric acid. The protonation of the phosphate anion is not likely to occur in the aprotic systems simulated here, and molecular dynamics simulations have shown that the phosphate- phosphate dimer is unstable in all the solvents studied here. Accordingly, the unbound form of the phosphate considered here is that corresponding to the isolated anionic compound.
43. Gelpí, J. I.; Kalko, S.; de la Cruz, X.; Barril, X.; Cirera, J,; Luque, F. J.; Orozco, M. Proteins: Struct., Funct., Genet. 2001, 45, 428.
44. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327.
45. Jorgensen, W. L. BOSS 4.2 Computer Program; Yale University: New Haven, CT, 2000.
46. Case, D. A.; Pearlman, D. A.; Caldwell, J. W.; Cheatham, T. E.; Ross, W. S.; Simmerling, C. L.; Darden, T. A.; Merz, K. M.; Stanton, R. V.; Cheng, A. L.; Vincent, J. J.; Crowley, M.; Ferguson, D. M.; Radmer, R. J.; Seibel, G. L.; Singh, U. C.; Weiner, P. K.; Kollman, P. A. AMBER-5: University of California: San Francisco, CA, 1997.
47. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA. 1998.
48. Pichierri, F. THEOCHEM 2002, 581, 117.
49. Camiolo, S; Gale, P. A. Chem. Commun. 2000, 1129.
50. Born, M. Z. Phys. 1920, 1, 45.
51. Orozco, M.; Luque, F. J. Chem. Rev. 2000, 100, 4187.
52. McDonald, N. A.; Duffy, E. M.; Jorgensen, W. L. J. Am. Chem. Soc. 1998, 120, 5014.
53. - are subjected to non-negligible statistical errors related to the dissociation of the ion pair along the mutation. Accordingly, all the free energy calculations reported in this part of the work should be taken with caution, since they might not be as accurate as simulations in pure solvents.
54. Sessler, J. Unpublished results.