Anion binding involving π-acidic heteroaromatic rings

Accounts of Chemical Research

Volumn 40, Issue 6, 2007, Pages 435-444

  Gamez, Patrick ^a   Mooibroek, Tiddo J ^a   Teat, Simon J ^b   Reedijk, J A N ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AROMATIC HYDROCARBON; HETEROCYCLIC COMPOUND; NITROGEN;

ARTICLE; BINDING SITE; CHEMISTRY; ELECTRON; MOLECULAR MIMICRY;

ANIONS; BINDING SITES; ELECTRONS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; MOLECULAR MIMICRY; NITROGEN;

EID: 34447298123     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar7000099     Document Type: Article

References (55)

1. Wright, E. M.; Diamond, J. M. Anion selectivity in biological systems. Physiol. Rev. 1977, 57, 109-156.
2. Bauduin, P.; Renoncourt, A.; Touraud, D.; Kunz, W.; Ninham, B. W. Hofmeister effect on enzymatic catalysis and colloidal structures. Curr. Opin. Colloid Interface Sci. 2004, 9, 43-47.
3. Jentsch, T. J.; Stein, V.; Weinreich, F.; Zdebik, A. A. Molecular structure and physiological function of chloride channels. Physiol. Rev. 2002, 82, 503-568.
4. Ashcroft, F. M. Ion Channels and Disease; Academic Press: San Diego, CA, 2000.
5. Guzmán, E. T. R.; Regil, E. O.; Gutiérrez, L. R. R.; Alberich, M. V. E.; Hernández, A. R.; Regil, E. O. Contamination of corn growing areas due to intensive fertilization in the high plane of Mexico. Water, Air, Soil Pollut. 2006, 175, 77-98.
6. Simmons, H. E.; Park, C. H. Macrobicyclic amines. I. Out-in isomerism of 1,(k + 2)-diazabicyclo[k.l.m]alkanes. J. Am. Chem. Soc. 1968, 90, 2428-2429.
7. Park, C. H.; Simmons, H. E. Macrobicyclic amines. II. Out-out in-in prototropy in 1,(k + 2)-diazabicyclo[k.l.m] alkaneammonium ions. J. Am. Chem. Soc. 1968, 90, 2429-2431.
8. Park, C. H.; Simmons, H. E. Macrobicyclic amines. III. Encapsulation of halide ions by in,in-1,(k + 2)-diazabicyclo[k.l.m.]alkane ammonium ions. J. Am. Chem. Soc. 1968, 90, 2431-2432.
9. Lehn, J. M.; Sonveaux, E.; Willard, A. K. Molecular recognition - Anion cryptates of a macrobicyclic receptor molecule for linear triatomic species. J. Am. Chem. Soc. 1978, 100, 4914-4916.
10. Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997.
11. Amendola, V.; Boiocchi, M.; Fabbrizzi, L.; Palchetti, A. What anions do inside a receptor's cavity: A trifurcate anion receptor providing both electrostatic and hydrogen-bonding interactions. Chem. - Eur. J. 2005, 11, 5648-5660.
12. Beer, P. D.; Gale, P. A. Anion recognition and sensing: The state of the art and future perspectives. Angew. Chem., Int. Ed. 2001, 40, 486-516.
13. Amendola, V.; Esteban-Gomez, D.; Fabbrizzi, L.; Licchelli, M. What anions do to N-H-containing receptors. Acc. Chem. Res. 2006, 39, 343-353.
14. Kang, S. O.; Begum, R. A.; Bowman-James, K. Amide-based ligands for anion coordination. Angew. Chem., Int. Ed. 2006, 45, 7882-7894.
15. Bowman-James, K. Alfred Werner revisited: The coordination chemistry of anions. Acc. Chem. Res. 2005, 38, 671-678.
16. Gale, P. A. Structural and molecular recognition studies with acyclic anion receptors. Acc. Chem. Res. 2006, 39, 465-475.
17. Demeshko, S.; Dechert, S.; Meyer, F. Anion-π interactions in a carousel copper(II)-triazine complex. J. Am. Chem. Soc. 2004, 126, 4508-4509.
18. de Hoog, P.; Gamez, P.; Mutikainen, H.; Turpeinen, U.; Reedijk, J. An aromatic anion receptor: Anion-π interactions do exist. Angew. Chem., Int. Ed. 2004, 43, 5815-5817.
19. 6 and electron-donor atoms. J. Org. Chem. 1997, 62, 4687-4691.
20. Zacharias, N.; Dougherty, D. A. Cation-π interactions in ligand recognition and catalysis. Trends Pharmacol. Sci. 2002, 23, 281-287.
21. Mascal, M.; Armstrong, A.; Bartberger, M. D. Anion-aromatic bonding: A case for anion recognition by π-acidic rings. J. Am. Chem. Soc. 2002, 124, 6274-6276.
22. - with olefinic and aromatic π receptors. Angew. Chem., Int. Ed. 2004, 43, 4650-4652.
23. Schneider, H. J. Mechanisms of molecular recognition - Investigations of organic host-guest complexes. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436.
24. Schneider, H. J.; Werner, F.; Blatter, T. Attractive interactions between negative charges and polarizable aryl parts of host-guest systems. J. Phys. Org. Chem. 1993, 6, 590-594.
25. Alkorta, I.; Rozas, I.; Elguero, J. Interaction of anions with perfluoro aromatic compounds. J. Am. Chem. Soc. 2002, 124, 8593-8598.
26. Quinonero, D.; Garau, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Counterintuitive interaction of anions with benzene derivatives. Chem. Phys. Lett. 2002, 359, 486-492.
27. Mascal, M. Precedent and theory unite in the hypothesis of a highly selective fluoride receptor. Angew. Chem., Int. Ed. 2006, 45, 2890-2893.
28. Frontera, A.; Saczewski, F.; Gdaniec, M.; Dziemidowicz-Borys, E.; Kurland, A.; Deya, P. M.; Quinonero, D.; Garau, C. Anion-π interactions in cyanuric acids: A combined crystallographic and computational study. Chem.-Eur. J. 2005, 11, 6560-6567.
29. 3 complexes. J. Phys. Chem. A 2005, 109, 9341-9345.
30. Garau, C.; Frontera, A.; Ballester, P.; Quinonero, D.; Costa, A.; Deya, P. M. A theoretical ab initio study of the capacity of several binding units for the molecular recognition of anions. Eur. J. Org. Chem. 2005, 179-183.
31. Quinonero, D.; Garau, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Structure and binding energy of anion-π and cation-π complexes: A comparison of MP2, RI-MP2, DFT, and DF-DFT methods. J. Phys. Chem. A 2005, 109, 4632-4637.
32. Garau, C.; Frontera, A.; Quinonero, D.; Ballester, P.; Costa, A.; Deya, P. M. Cation-π vs anion-π interactions: A complete π-orbital analysis. Chem. Phys. Lett. 2004, 399, 220-225.
33. Garau, C.; Frontera, A.; Quinonero, D.; Ballester, P.; Costa, A.; Deya, P. M. Cation-π versus anion-π interactions: Energetic, charge transfer, and aromatic aspects. J. Phys. Chem. A 2004, 108, 9423-9427.
34. Garau, C.; Frontera, A.; Quinonero, D.; Ballester, P.; Costa, A.; Deya, P. M. Cation-π versus anion-π interactions: A comparative ab initio study based on energetic, electron charge density and aromatic features. Chem. Phys. Lett. 2004, 392, 85-89.
35. Kim, D.; Tarakeshwar, P.; Kim, K. S. Theoretical investigations of anion-π interactions: The role of anions and the nature of π systems. J. Phys. Chem. A 2004, 108, 1250-1258.
36. Garau, C.; Frontera, A.; Quinonero, D.; Ballester, P.; Costa, A.; Deya, P. M. A topological analysis of the electron density in anion-π interactions. ChemPhysChem 2003, 4, 1344-1348.
37. Garau, C.; Quinonero, D.; Frontera, A.; Costa, A.; Ballester, P.; Deya, P. M. s-Tetrazine as a new binding unit in molecular recognition of anions. Chem. Phys. Lett. 2003, 370, 7-13.
38. Clements, A.; Lewis, M. Arene-cation interactions of positive quadrupole moment aromatics and arene-anion interactions of negative quadrupole moment aromatics. J. Phys. Chem. A 2006, 110, 12705-12710.
39. de Hoog, P.; Gamez, P.; Driessen, W. L.; Reedijk, J. New polydentate and polynucleating N-donor ligands from amines and 2,4,6-trichloro-1,3,5-triazine. Tetrahedron Lett. 2002, 43, 6783-6786.
40. Gamez, P.; de Hoog, P.; Lutz, M.; Spek, A. L.; Reedijk, J. Coordination compounds from 1,3,5-triazine-derived multidirectional ligands: Application in oxidation catalysis. Inorg. Chim. Acta 2003, 351, 319-325.
41. Gamez, P.; Reedijk, J. 1,3,5-Triazine-based synthons in supramolecular chemistry. Eur. J. Inorg. Chem. 2006, 29-42.
42. Mooibroek, T. J.; Gamez, P. The s-triazine ring, a remarkable unit to generate supramolecular interactions. Inorg. Chim. Acta 2007, 360, 381-404.
43. Maheswari, P. U.; Modec, B.; Pevec, A.; Kozlevcar, B.; Massera, C.; Gamez, P.; Reedijk, J. Crystallographic evidence of nitrate-π interactions involving the electron-deficient 1,3,5-triazine ring. Inorg. Chem. 2006, 45, 6637-6645.
44. I complexes with π-acidic aromatic rings. J. Am. Chem. Soc. 2006, 128, 5895-5912.
45. Casellas, H.; Massera, C.; Buda, F.; Gamez, P.; Reedijk, J. Crystallographic evidence of theoretically novel anion-π interactions. New J. Chem. 2006, 30, 1561-1566.
46. Gural'skiy, I. A.; Solntsev, P. V.; Krautscheid, H.; Domasevitch, K. V. Metal-organic frameworks exhibiting strong anion-π interactions. Chem. Commun. 2006, 4808-4810.
47. Berryman, O. B.; Hof, F.; Hynes, M. J.; Johnson, D. W. Anion-π interaction augments halide binding in solution. Chem. Commun. 2006, 506-508.
48. Dutzler, R.; Campbell, E. B.; Cadene, M.; Chait, B. T.; MacKinnon, R. X-ray structure of a ClC chloride channel at 3.0 Å reveals the molecular basis of anion selectivity. Nature 2002, 415, 287-294.
49. Gorteau, V.; Bollot, G.; Mareda, J.; Perez-Velasco, A.; Matile, S. Rigid oligonaphthalenediimide rods as transmembrane anion-π slides. J. Am. Chem. Soc. 2006, 128, 14788-14789.
50. Gung, B. W.; Xue, X. W.; Reich, H. J. Off-center oxygen-arene interactions in solution: A quantitative study. J. Org. Chem. 2005, 70, 7232-7237 and references therein.
51. Sarkhel, S.; Rich, A.; Martin, E. Water-nucleobase "stacking": H-π and lone pair-π interactions in the atomic resolution crystal structure of an RNA pseudoknot. J. Am. Chem. Soc. 2003, 125, 8998-8999.
52. Mooibroek, T. J.; Teat, S. J.; Massera, C.; Gamez, P.; Reedijk, J. Crystallographic and theoretical evidence of acetonitrile-π interactions with the electron-deficient 1,3,5-triazine ring. Cryst. Growth Des. 2006, 6, 1569-1574.
53. Ma, J. C.; Dougherty, D. A. The cation-π interaction. Chem. Rev. 1997, 97, 1303-1324.
54. Egli, M.; Sarkhel, S. Lone pair-aromatic interactions: To stabilize or not to stabilize. Acc. Chem. Res. 2007, 40, 197-205.
55. II obtained at elevated temperature and pressure. Eur. J. Inorg. Chem. 2005, 2902-2908.