Erratum: Versatility of an intramolecularly hydrogen-bonded 4-(N,N-dimethylamino)benzoate group as a signaling subunit for anion recognition (Tetrahedron (2005) 61 (5866) DOI: 10.1016/j.tet.2005.04.006);Versatility of an intramolecularly hydrogen-bonded 4-(N,N-dimethylamino) benzoate group as a signaling subunit for anion recognition

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5866-5875

  Hou, Xiaohong ^a   Kobiro, Kazuya ^a  

^a KOCHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

4 (N,N Dimethylamino)benzoate group; Anion recognition; CD titration; Chiral guanidinium ion; Dual fluorescence titration; Intramolecular hydrogen bonding; NMR titration

Indexed keywords

4 (N,N DIMETHYLAMINO)BENZOATE; AMINOBENZOIC ACID DERIVATIVE; PHOSPHATE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; FLUORESCENCE; HYDROGEN BOND; HYDROPHILICITY; LIPOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; TITRIMETRY;

EID: 19744365906     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.073     Document Type: Erratum

References (68)

1. A. Bianchi K. Bowman-James E. Garcia-España Supramolecular chemistry of anions 1997 Wiley-VCH New York
2. J.W. Steed, and J.L. Atwood Supramolecular chemistry 2000 Wiley West Sussex
3. For reviews, see: (a) F.P. Schmidtchen, and M. Berger Chem. Rev. 97 1997 1609 1646
4. P.A. Gale Coord. Chem. Rev. 199 2000 181 233
5. P.A. Gale Coord. Chem. Rev. 213 2001 79 128
6. For reviews, see: (a) P.D. Beer, and P.A. Gale Angew. Chem., Int. Ed. 40 2001 486 516
7. R. Martínez-Máñez, and F. Sancenón Chem. Rev. 103 2003 4419 4476
8. S. Nishizawa, R. Kato, T. Hayashita, and N. Teramae Anal. Sci. 14 1998 595 597
9. T. Hayashita, T. Onodera, R. Kato, S. Nishizawa, and N. Teramae Chem. Commun. 2000 755 756
10. H. Miyaji, W. Sato, J.L. Sessler, and V.M. Lynch Tetrahedron Lett. 41 2000 1369 1373
11. R. Kato, S. Nishizawa, T. Hayashita, and N. Teramae Tetrahedron Lett. 42 2001 5053 5056
12. P. Piatek, and J. Jurczak Chem. Commun. 2002 2450 2451
13. H. Miyaji, S.R. Collinson, I. Prokeš, and J.H.R. Tucker Chem. Commun. 2003 64 65
14. H. Miyaji, W. Sato, and J.L. Sessler Angew. Chem., Int. Ed. 39 2000 1777 1778
15. H. Miyaji, and J.L. Sessler Angew. Chem., Int. Ed. 40 2001 154 157
16. D. Jiménez, R. Martínez-Máñez, F. Sancenón, and J. Soto Tetrahedron Lett. 43 2002 2823 2825
17. D.H. Lee, K.H. Lee, and J.-I. Hong Org. Lett. 3 2001 5 8
18. D.H. Lee, H.-Y. Lee, K.H. Lee, and J.-I. Hong Chem. Commun. 2001 1188 1189
19. K.H. Lee, H.-Y. Lee, D.H. Lee, and J.-I. Hong Tetrahedron Lett. 42 2001 5447 5449
20. C. Lee, D.H. Lee, and J.-I. Hong Tetrahedron Lett. 42 2001 8665 8668
21. F. Sancenón, R. Martínez-Máñez, and J. Soto Angew. Chem., Int. Ed. 41 2002 1416 1419
22. D.H. Lee, J.H. Im, S.U. Son, Y.K. Chung, and J.-I. Hong J. Am. Chem. Soc. 125 2003 7752 7753
23. P.D. Beer, M.G.B. Drew, D. Hesek, and R. Jagessar J. Chem. Soc., Chem. Commun. 1995 1187 1190
24. S.B. Starnes, S. Arungundram, and C.H. Saundars Tetrahedron Lett. 43 2002 7785 7788
25. Y.-H. Kim, and J.-I. Hong Chem. Commun. 2002 512 513
26. For a review, see: J.L. Sessler, and J.M. Davis Acc. Chem. Res. 34 2001 989 997
27. D.H. Vance, and A.W. Czarnik J. Am. Chem. Soc. 116 1994 9397 9398
28. S. Nishizawa, H. Kaneda, T. Uchida, and N. Teramae J. Chem. Soc., Perkin Trans. 2 1998 2325 2328
29. Y. Kubo, M. Tsukahara, S. Ishihara, and S. Tokita Chem. Commun. 2000 653 654
30. H. Yoshida, K. Saigo, and K. Hiratani Chem. Lett. 2000 116 117
31. G. Hennrich, H. Sonnenschein, and U. Resch-Genger Tetrahedron Lett. 42 2001 2805 2808
32. L.A. Cabell, M.D. Best, J.J. Lavigne, S.E. Schneider, D.M. Perreault, M.K. Monahan, and E.V. Anslyn J. Chem. Soc., Perkin Trans. 2 2001 315 323
33. L. Fabbrizzi, M. Licchelli, F. Mancin, M. Pizzeghello, G. Rabaioli, A. Taglietti, P. Tecilla, and U. Tonellato Chem. Eur. J. 8 2002 94 101
34. Y. Kubo, S. Ishihara, M. Tsukahara, and S. Tokita J. Chem. Soc., Perkin Trans. 2 2002 1455 1460
35. S.K. Kim, and J. Yoon Chem. Commun. 2002 770 771
36. J.Y. Kwon, Y.J. Jang, S.K. Kim, K.-H. Lee, J.S. Kim, and J. Yoon J. Org. Chem. 69 2004 5155 5157
37. P.D. Beer, F. Szemes, V. Balzani, C.M. Salà, M.G.B. Drew, S.W. Dent, and M. Maestri J. Am. Chem. Soc. 119 1997 11864 11875
38. M.J. Deetz, and B.D. Smith Tetrahedron Lett. 39 1998 6841 6844
39. S. Watanabe, O. Onogawa, Y. Komatsu, and K. Yoshida J. Am. Chem. Soc. 120 1998 229 230
40. P.D. Beer, V. Timoshenko, M. Maestri, P. Passaniti, and V. Balzani Chem. Commun. 1999 1755 1756
41. S. Watanabe, N. Higashi, M. Kobayashi, K. Hamanaka, Y. Takata, and K. Yoshida Tetrahedron Let. 41 2000 4583 4586
42. M.E. Padilla-Tosta, J.M. Lloris, R. Martínez-Máñez, T. Pardo, J. Soto, A. Benito, and M.D. Marcos Inorg. Chem. Commun. 3 2000 45 48
43. For a review, see: P.D. Beer Acc. Chem. Res. 31 1998 71 80
44. X-ray structure analyses on guanidinium ion complexes with anions were reported: (a) L. Chertanova, and C. Pascard Acta Crystallogr. B52 1996 677 684
45. M. Haj-Zaroubi, N.W. Mitzel, and F.P. Schmidtchen Angew. Chem., Int. Ed. 41 2002 104 107
46. K. Kobiro, and Y. Inoue J. Am. Chem. Soc. 125 2003 421 427
47. K.A. Schug, and W. Lindner Chem. Rev. 105 2005 67 114
48. K.A. Connors Binding constants. The measurement of molecular complex stability 1987 Wiley-Interscience New York pp 189-215
49. C.S. Wilcox H.-J. Schneider H. Dürr Frontiers in supramolecular organic chemistry and photochemistry 1991 VCH Weinheim 123 143
50. M.J. Hynes J. Chem. Soc., Dalton Trans. 1993 311 312
51. 1:1 was calculated, instead, by the use of titration data on CD shown in Figure 9 B.
52. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902 3903
53. 6d,22b.
54. 3CN, while the spectral change was too small to discuss in detail. Host 1 is instead CD active, because the DMAB group is connected to the chiral guanidinium ion moiety. Thus, we utilized CD spectra instead of UV-vis spetra to get complexation information through the DMAB group.
55. N. Berova, K. Nakanishi, and R.W. Woody Circular dichromism, principle and applications 2nd ed. 2000 Wiley-VCH New York
56. D.A. Lightner, and J.E. Gurst Organic conformational analysis and stereochemistry from circular dichromism spectroscopy 2000 Wiley-VCH New York
57. D.J. Cowley, and P.J. Healy Proc. R. Ir. Acad. Soc. B77B 1977 397
58. Z.R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D.J. Cowley, and W. Baumann Nouv. J. Chim. 3 1979 443
59. W. Rettig Angew. Chem., Int. Ed. 25 1986 971
60. R. Hayashi, S. Tazuke, and C.W. Frank Macromolecules 20 1987 983 988
61. S. Tazuke, R.K. Guo, and R. Hayashi Macromolecules 22 1989 729 734
62. S. Tazuke, R.K. Guo, T. Ikeda, and T. Ikeda Macromolecules 23 1990 1208 1211
63. J. Paczkowski, and D.C. Neckers Macromolecules 24 1991 3013 3016
64. J. Paczkowshi, and D.C. Neckers J. Polym. Sci., Polym. Chem. 31 1993 841
65. W. Rettig J. Mattay Topics in current chemistry Vol. 169 1994 Springer Berlin 253 299
66. F.-Y. Wu, and Y.-B. Jiang Chem. Phys. Lett. 355 2002 438 444
67. F.-Y. Wu, Z. Li, Z.-C. Wen, N. Zhou, Y.-F. Zhao, and Y.-B. Jiang Org. Lett. 4 2002 3203 3205
68. - would lead to decrease of the LE intensity with increase of the TICT intensity. Judging from the increment of the TICT intensity, the decrease of the LE intensity seems to be very small. The expected slight decrease of the LE intensity could overlap with the large increase of the LE intensity which is caused by the active participation of the lipophilic TBA to show the observed intricate increase of the LE profile.