Effect of spacer geometry on oxoanion binding by bis- and tetrakis-thiourea hosts

Tetrahedron

Volumn 64, Issue 11, 2008, Pages 2530-2536

  Leung, Annie N ^a   Degenhardt, Dave A ^a   Bühlmann, Philippe ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' [[2,2,2 TRIFLUORO 1(TRIFLUOROMETHYL)ETHYLIDENE]BIS(6 METHYL 3,1 PHENYLENE)] BIS[N' PHENYLTHIOUREA]; 1,2 CYCLOHEXANEDIYLBIS[N' PHENYLTHIOUREA]; ANION; BIS(THIOUREA); CHLORIDE; DIHYDROGEN ARSENATE; DIHYDROGEN PHOSPHATE; DIMETHYL SULFOXIDE; INORGANIC SALT; N,N'' [1,4 PHENYLENEBIS(METHYLENE)]BIS[N' PHENYLTHIOUREA]; N,N'' [2,7 NAPHTHALENDIYLBIS(METHYLENE)]BIS[N' PHENYLTHIOUREA]; TETRAKIS(THIOUREA); THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; PRIORITY JOURNAL; SOLVATION; SYNTHESIS; TITRIMETRY;

EID: 38749134838     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.026     Document Type: Article

References (67)

1. Izatt R.M., Pawlak K., Bradshaw J.S., and Bruening R.L. Chem. Rev. 91 (1991) 1721
2. In: Bianchi A., Bowman-James K., and Garcia-Espana J.E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York, NY
3. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
4. Bühlmann P., Pretsch E., and Bakker E. Chem. Rev. 98 (1998) 1593
5. Antonisse M.M.G., and Reinhoudt D.N. Electroanalysis 11 (1999) 1034
6. Snowden T.S., and Anslyn E.V. Curr. Opin. Chem. Biol. 3 (1999) 740
7. Hartley J.H., James T.D., and Ward C.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3155
8. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486
9. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419
10. Katayev E.A., Ustynyuk Y.A., and Sessler J.L. Coord. Chem. Rev. 250 (2006) 3004
11. Sessler J.L., Gale P.A., and Cho W.-S. Anion Receptor Chemistry (2006), RSC, Cambridge
12. Smith P.J., Reddington M.V., and Wilcox C.S. Tetrahedron Lett. 33 (1992) 6085
13. Fan E., Van Arman S.A., Kincaid S., and Hamilton A.D. J. Am. Chem. Soc. 115 (1993) 369
14. Albert J.S., and Hamilton A.D. Tetrahedron Lett. 34 (1993) 7363
15. Kelly T.R., and Kim M.H. J. Am. Chem. Soc. 116 (1994) 7072
16. Nishizawa S., Bühlmann P., Iwao M., and Umezawa Y. Tetrahedron Lett. 36 (1995) 6483
17. Hamann B.C., Branda N.R., and Rebek Jr. J. Tetrahedron Lett. 34 (1993) 6837
18. Bühlmann P., Nishizawa S., Xiao K.P., and Umezawa Y. Tetrahedron 53 (1997) 1647
19. Xiao K.P., Bühlmann P., Nishizawa S., Amemiya S., and Umezawa Y. Anal. Chem. 69 (1997) 1038
20. Bryantsev V.S., and Hay B.P. J. Am. Chem. Soc. 128 (2006) 2035
21. Blanco J.L.J., Benito J.M., Mellet C.O., and Fernandez J.M.G. Org. Lett. 1 (1999) 1217
22. Hayashita T., Onodera T., Kato R., Nishizawa S., and Teramae N. Chem. Commun. (2000) 755
23. Kato R., Nishizawa S., Hayashita T., and Teramae N. Tetrahedron Lett. 42 (2001) 5053
24. Gunnlaugsson T., Davis A.P., and Glynn M. Chem. Commun. (2001) 2556
25. Qian X., and Liu F. Tetrahedron Lett. 44 (2003) 795
26. Gunnlaugsson T., Davis A.P., Hussey G.M., Tierney J., and Glynn M. Org. Biomol. Chem. 2 (2004) 1856
27. Hennrich G., Sonnenschein H., and Resch-Genger U. Tetrahedron Lett. 42 (2001) 2805
28. Nie L., Li Z., Han J., Zhang X., Yang R., Liu W.-X., Wu F.-Y., Xie J.-W., Zhao Y.-F., and Jiang Y.-B. J. Org. Chem. 69 (2004) 6449
29. Linton B.R., Goodman M.S., Fan E., van Arman S.A., and Hamilton A.D. J. Org. Chem. 66 (2001) 7313
30. Chrisstoffels L.A.J., de Jong F., Reinhoudt D.N., Sivelli S., Gazzola L., Casnati A., and Ungaro R. J. Am. Chem. Soc. 121 (1999) 10142
31. Kondo S., and Sato M. Tetrahedron 62 (2006) 4844
32. Pfeffer F.M., Gunnlaugsson T., Jensen P., and Kruger P.E. Org. Lett. 7 (2005) 5357
33. Blanco J.L.J., Bootello P., Benito J.M., Mellet C.O., and Fernandez J.M.G. J. Org. Chem. 71 (2006) 5136
34. Boerringer H., Grave L., Nissink J.W.M., Chrisstoffels L.A.J., van der Maas J.H., Verboom W., de Jong F., and Reinhoudt D.N. J. Org. Chem. 63 (1998) 4174
35. Sasaki S., Citterio D., Ozawa S., and Suzuki K. J. Chem. Soc., Perkin Trans. 2 (2001) 2309
36. Herges R., Dikmans A., Jana U., Köhler F., Jones P.G., Dix I., Fricke T., and König B. Eur. J. Org. Chem. (2002) 3004
37. Okumura Y., Murakami S., Maeda H., Matsumura N., and Mizuno K. Tetrahedron Lett. 44 (2003) 8183
38. Sasaki S., Mizuno M., Naemura K., and Tobe Y. J. Org. Chem. 65 (2000) 275
39. Lee K.H., and Hong J.-I. Tetrahedron Lett. 41 (2000) 6083
40. Turncharem G., Tuntulani T., Coles S.J., Hursthouse M.B., and Kilburn J.D. Org. Lett. 5 (2003) 4971
41. Hisaki I., Sasaki S., Hirose K., and Tobe Y. Eur. J. Org. Chem. (2007) 607
42. Benito J.M., Gomez-Garcia M., Blanco J.L., Mellet C.O., and Fernandez J.M.G. J. Org. Chem. 66 (2001) 1366
43. Dahan A., Ashkenazi T., Kuznetsov V., Makievski S., Drug E., Fadeev L., Bramson M., Schokoroy S., Rozenshine-Kemelmakher E., and Gozin M. J. Org. Chem. 72 (2007) 2289
44. Nishizawa S., Bühlmann P., Xiao K.P., and Umezawa Y. Anal. Chim. Acta 358 (1998) 35
45. Shioya T., Nishizawa S., and Teramae N. J. Am. Chem. Soc. 120 (1998) 11534
46. Nishizawa S., Yokobori T., Kato R., Yoshimoto K., Kamaishi T., and Teramae N. Analyst 128 (2003) 663
47. Watts A.S., Gavalas V.G., Cammers A., Andrada P.S., Alajarin M., and Bachas L.G. Sens. Actuators, B 121 (2007) 200
48. Rodriguez-Lucena D., Benito J.M., Mellet C.O., and Fernandez J.M.G. Chem. Commun. (2007) 831
49. Yeo W.-S., and Hong J.-I. Tetrahedron 39 (1998) 8137
50. Lee D.H., Lee H.Y., and Hong J.-I. Tetrahedron Lett. 43 (2002) 7273
51. Lee D.H., Im J.H., Lee J.-H., and Hong J.-I. Tetrahedron Lett. 43 (2002) 9637
52. Hay B.P., Firman T.K., and Moyer B.A. J. Am. Chem. Soc. 127 (2005) 1810
53. Choi I.S., Li X., Simanek E.E., Akaba R., and Whitesides G.M. Chem. Mater. 11 (1999) 684
54. Smith J., Liras J.L., Schneider S.E., and Anslyn E.V. J. Org. Chem. 6 (1996) 8811
55. Bordwell F.G., Algrim D.J., and Harrelson Jr. J.A. J. Am. Chem. Soc. 110 (1988) 5903
56. Koltun W.L. Biopolymers 3 (1965) 665
57. Raposo J.C., Sanz J., Zuloaga O., Olazabal M.A., and Madariaga J.M. Talanta 57 (2002) 849
58. Ferraris G., Jones D.W., and Yerkess J. Acta Crystallogr. B28 (1972) 2430
59. Dickens B., Schroeder L.W., and Brown W.E. Acta Crystallogr. B29 (1973) 2057
60. Wang S., Wu C., and Liu S. J. Solid State Chem. 113 (1994) 37
61. Magnera T.F., Caldwell G., Sunner J., Ikuta S., and Kebarle P. J. Am. Chem. Soc. 106 (1984) 6140
62. Taft R.W., and Bordwell F.G. Acc. Chem. Res. 21 (1988) 463
63. Arshadi M., Yamdagni R., and Kebarle P. J. Phys. Chem. 74 (1970) 1475
64. Blades A., Ho Y., and Kebarle P. J. Phys. Chem. 100 (1996) 2443
65. Blades A.T., Klassen J.S., and Kebarle P. J. Am. Chem. Soc. 117 (1995) 10563
66. Rony P.R., and Neff R.O. J. Am. Chem. Soc. 95 (1973) 2896
67. Connors K.A. Binding Constants (1987), John Wiley and Sons, New York, NY