SCOPUS 정보 검색 플랫폼

Letters in Organic Chemistry

Volumn 4, Issue 2, 2007, Pages 112-119

Triindolylmethane: Selective receptor for chloride anion

(3) Oi, Wataru a Nishiki, Makoto a Ito, Kazuaki a

a YAMAGATA UNIVERSITY (Japan)

Author keywords

Anion recognition; Chloride anion selectivity; Hydrogen bond; Quaternary ammonium salt; Triindolylmethane

Indexed keywords

EID: 34247583437 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017807780414136 Document Type: Article

Times cited : (13)

References (34)

1
- 0000231821
- Atwood, J. L, Davies, J. E, MacNicol, D. D, Vogtle, F. Ed, Elsevier Sience Ltd, Oxfords
- Seel, C.; de Mendoza, J.; Reetz, M. T. In Comprehensive Supramolcular Chemistry, Atwood, J. L.; Davies, J. E.; MacNicol, D. D.; Vogtle, F. Ed.; Elsevier Sience Ltd., Oxfords, 1996; Vol. 2, pp. 519-562.
- (1996) Comprehensive Supramolcular Chemistry , vol.2 , pp. 519-562
- Seel, C.¹ de Mendoza, J.² Reetz, M.T.³

2
- 0031192717
- Schmidtchen, F. P.; Berger, M. Chem. Rev., 1997, 97, 1609.
- (1997) Chem. Rev , vol.97 , pp. 1609
- Schmidtchen, F.P.¹ Berger, M.²

3
- 0002036125
- Beer, P. A. Acc. Chem. Res., 1998, 31, 71.
- (1998) Acc. Chem. Res , vol.31 , pp. 71
- Beer, P.A.¹

4
- 0034793619
- Gale, P. A.; Anzenbacher, P.; Sessler, J. L. Coord. Chem. Rev., 2000, 222, 57.
- (2000) Coord. Chem. Rev , vol.222 , pp. 57
- Gale, P.A.¹ Anzenbacher, P.² Sessler, J.L.³

5
- 0035793285
- Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. Engl., 2001, 40, 486.
- (2001) Angew. Chem., Int. Ed. Engl , vol.40 , pp. 486
- Beer, P.D.¹ Gale, P.A.²

6
- 0038547874
- Gale P. A. Coord. Chem. Rev., 2003, 240, 191.
- (2003) Coord. Chem. Rev , vol.240 , pp. 191
- Gale, P.A.¹

7
- 0242385371
- Sukasi, C.; Tuntulani, T. Chem. Soc. Rev., 2003, 32, 192.
- (2003) Chem. Soc. Rev , vol.32 , pp. 192
- Sukasi, C.¹ Tuntulani, T.²

8
- 23744434373
- Gale P. A. Chem. Commun., 2005, 3761.
- (2005) Chem. Commun , pp. 3761
- Gale, P.A.¹

9
- 33745711873
- Amendola, V.; Esteban-Gomez, D.; Fabbrizzi, L.; Licchelli, M. Acc. Chem. Res., 2006, 39, 343.
- (2006) Acc. Chem. Res , vol.39 , pp. 343
- Amendola, V.¹ Esteban-Gomez, D.² Fabbrizzi, L.³ Licchelli, M.⁴

10
- 33751158907
- Scheerder, J.; Fochi, M.; Rngbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem., 1994, 59, 7815.
- (1994) J. Org. Chem , vol.59 , pp. 7815
- Scheerder, J.¹ Fochi, M.² Rngbersen, J.F.J.³ Reinhoudt, D.N.⁴

11
- 0027851753
- Hung, C.-Y.; Höpfner, T.; Thummel, R. P. J. Am. Chem. Soc., 1993, 115, 12601.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 12601
- Hung, C.-Y.¹ Höpfner, T.² Thummel, R.P.³

12
- 33750312767
- Kwon, T. H.; Jeong, K.-S. Tetrahedron Lett., 2006, 47, 8539.
- (2006) Tetrahedron Lett , vol.47 , pp. 8539
- Kwon, T.H.¹ Jeong, K.-S.²

13
- 2942566106
- Chakrabarty, M.; Sarkar, S.; Linden, A.; Stein, B. K. Synth. Commun., 2004, 34, 1801.
- (2004) Synth. Commun , vol.34 , pp. 1801
- Chakrabarty, M.¹ Sarkar, S.² Linden, A.³ Stein, B.K.⁴

14
- 0037999878
- Guidotti, S.; Camurati, I.; Focante, F.; Angellini, L.; Moscardi, G.; Resconi, L.; Leardini, R.; Nanni, D.; Mercandelli, P.; Sironi, A.; Beringhelli, T.; Maggioni, D. J. Org. Chem., 2003, 68, 5445.
- (2003) J. Org. Chem , vol.68 , pp. 5445
- Guidotti, S.¹ Camurati, I.² Focante, F.³ Angellini, L.⁴ Moscardi, G.⁵ Resconi, L.⁶ Leardini, R.⁷ Nanni, D.⁸ Mercandelli, P.⁹ Sironi, A.¹⁰ Beringhelli, T.¹¹ Maggioni, D.¹²

15
- 34247599312
- 1a: melting point 320-321 °C (lit. 319-320 °C, 13, 1H-NMR (CDCl3) δ: 2.18 (s, 9H, Mex3, 6.22 (s, 1H, CH, 7.15 (ddd, 3H, Ar-Hx3, J, 1.5, 7.0, 7.5 Hz, 7.18 (ddd. 3H, Ar-Hx6, J, 1.5, 7.0, 7.5 Hz, 7.25 (dd, 3H, Ar-Hx3, J, 1.5, 7.0 Hz, 7.58 (dd, 3H, Ar-Hx6, J, 1.5, 7.5 Hz, 7.70 (bs, 3H, NHx3, 13C-NMR (CDCl3) δ: 8.4, 33.6, 108.9, 111.1, 118.6, 119.7, 122.0, 129.5, 131.5, 135.3. IR (in CHCl3, concentration, 10 mM, 3442 cm-1. FAB-MS: 404 (M+H, Elemental Analysis: Calcd. for C28 H25 N3, C: 83.34, H: 6.24, N: 10.41, Found: C: 83.54, H: 6.04, N: 10.22, 1b: melting point 230 °C (decomposed, 1H-NMR (CDCl3) δ: 2.17 (s, 6H, Mex2, 4.88 (bs, 1H, OH, 6.10 (a, 1H, CH, 6.87 (dd, 1H, Ar-H, J= 1.5, 7.5 Hz, 6.93 (ddd, 1H, Ar-H, J, 1.5, 7.5, 7.5 Hz, 7.05 dd, 1H, Ar-H
- 2, C: 85.68 %; H: 6.33 %; N: 7.99%. Found: C: 85.88 %; H: 6.42 %; N: 7.75 %.

16
- 0036599278
- Ito, K.; Miki, H.; Ohba, Y. Yakugaku Zasshi, 2002, 122, 413.
- (2002) Yakugaku Zasshi , vol.122 , pp. 413
- Ito, K.¹ Miki, H.² Ohba, Y.³

17
- 33845642986
- Ito, K.; Takahashi, M.; Hoshino, T.; Nishiki, M.; Ohba, Y. Lett. Org. Chem., 2006, 3, 735.
- (2006) Lett. Org. Chem , vol.3 , pp. 735
- Ito, K.¹ Takahashi, M.² Hoshino, T.³ Nishiki, M.⁴ Ohba, Y.⁵

18
- 21144441067
- Kodansha, Tokyo
- Nishio, M. Introduction of Intermolecular Force in Organic Chemistry, Kodansha, Tokyo, 2000.
- (2000) Introduction of Intermolecular Force in Organic Chemistry
- Nishio, M.¹

19
- 0037131282
- Ito, K.; Noike, M.; Kida, A.; Ohba, Y. J. Org. Chem., 2002, 67, 7519.
- (2002) J. Org. Chem , vol.67 , pp. 7519
- Ito, K.¹ Noike, M.² Kida, A.³ Ohba, Y.⁴

20
- 0037287562
- Ito, K.; Sato, T.; Ohba, Y. J. Heterocycl. Chem., 2003, 40, 77.
- (2003) J. Heterocycl. Chem , vol.40 , pp. 77
- Ito, K.¹ Sato, T.² Ohba, Y.³

21
- 18744386966
- Ito, K.; Nagase, K.; Morohashi, N.; Ohba, Y. Chem. Pharm. Bull., 2005, 53, 90.
- (2005) Chem. Pharm. Bull , vol.53 , pp. 90
- Ito, K.¹ Nagase, K.² Morohashi, N.³ Ohba, Y.⁴

22
- 26444521199
- Ito, K.; Nishiki, M.; Ohba, Y. Chem. Pharm. Bull., 2005, 53, 1352.
- (2005) Chem. Pharm. Bull , vol.53 , pp. 1352
- Ito, K.¹ Nishiki, M.² Ohba, Y.³

23
- 0033525057
- Gung, B. W.; MacKay, J. A.; Zou, D. J. Org. Chem., 1999, 64, 700.
- (1999) J. Org. Chem , vol.64 , pp. 700
- Gung, B.W.¹ MacKay, J.A.² Zou, D.³

24
- 84936887577
- Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc., 1992, 114, 8316.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 8316
- Diaz, H.¹ Espina, J.R.² Kelly, J.W.³

25
- 0011034289
- Tsang, K. Y.; Diaz, H.; Graciani, N., Kelly, J. W. J. Am. Chem. Soc., 1994, 116, 3988.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 3988
- Tsang, K.Y.¹ Diaz, H.² Graciani, N.³ Kelly, J.W.⁴

26
- 0030811193
- Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc., 1997, 119, 5413.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 5413
- Nowick, J.S.¹ Pairish, M.² Lee, I.Q.³ Holmes, D.L.⁴ Ziller, J.W.⁵

27
- 34247604951
- In competitive solvents, such as water and DMSO, the chemical shifts of solvent-exposed amide NH protons exhibit large temperature dependencies, while intramolecularly hydrogen-bonded amide NH protons, namely solvent-shielded protons, exhibit small temperature dependencies
- In competitive solvents, such as water and DMSO, the chemical shifts of solvent-exposed amide NH protons exhibit large temperature dependencies, while intramolecularly hydrogen-bonded amide NH protons, namely solvent-shielded protons, exhibit small temperature dependencies.

28
- 0031160103
- Baxter, N. J.; Williamson, M. P. J. Biomol. NMR, 1997, 9, 359.
- (1997) J. Biomol. NMR , vol.9 , pp. 359
- Baxter, N.J.¹ Williamson, M.P.²

29
- 33746117937
- Ito, K.; Ito, T.; Takasawa, T.; Ohba, Y. Lett. Org. Chem., 2006. 3, 260.
- (2006) Lett. Org. Chem , vol.3 , pp. 260
- Ito, K.¹ Ito, T.² Takasawa, T.³ Ohba, Y.⁴

30
- 34247554862
- -1 increased. The IR spectral change was ascribed to hydrogen bonding between NH protons and anion component of 2.
- -1 increased. The IR spectral change was ascribed to hydrogen bonding between NH protons and anion component of 2.

31
- 34247602038
- 1H NMR chemical shift change (Δδ) of the NH proton of 1 that is sensitive to complex formation. The data were plotted in the form Δδx [1] versus [1]/[1] + [2]), and the position of the maximum indicates the stoichiometry of the complex.
- 1H NMR chemical shift change (Δδ) of the NH proton of 1 that is sensitive to complex formation. The data were plotted in the form Δδx [1] versus [1]/[1] + [2]), and the position of the maximum indicates the stoichiometry of the complex.

32
- 34247605941
- Hirose, K. J. Inc. Phenom. Macrocycl. Chem, 2001, 122, 193. Stability constants (Ks) were obtained by 1H-NMR titration experiments, performed directly in the NMR tube using a micropipette to add known amounts (0, 50, 100, 150, 200, 250, 300, 350, 400, 450, 500 μl) of quaternary ammonium salt (2) stock solution (concentration, 10.0 mM) in CDCl3 to a solution of indolylmethanes (1, 700 μl, concentration, 5.76 mM) in CDCl3. A 1:1 association of indolylmethanes (1) and quaternary ammonium salts (2) was previously demonstrated by Job plots, therefore, experimental data were fit to the equation of the 1:1 binding isotherm. All titration experiments were performed in CDCl3 at 297 K and 500 MHz
- 3 at 297 K and 500 MHz.

33
- 34247598820
- Perrin, D. D. Pure Appl. Chem., 1969, 20, 113.
- (1969) Pure Appl. Chem , vol.20 , pp. 113
- Perrin, D.D.¹

34
- 34247598322
- CS Chem3D Pro(R) version 3.5.2 for windows, Cambridge Soft, Massachusetts, 1997
- CS Chem3D Pro(R) version 3.5.2 for windows, Cambridge Soft, Massachusetts, 1997.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.