Molecular recognition of neutral substrates by new tetraaminocalix[4]arene derivative

Bulletin of the Korean Chemical Society

Volumn 30, Issue 6, 2009, Pages 1247-1251

  Nimse, Satish Balasaheb ^a   Song, Keum Soo ^b   Jung, Chan Yong ^b   Eoum, Woon Yong ^b   Kim, Taisun ^a  

^a Hallym University   (South Korea)

^b Biometrix Technology Inc   (South Korea)

Author keywords

Deep cavity; Molecular recognition; Neutral substrates; Tetraaminocalixarene

Indexed keywords

ARENE DERIVATIVES; AROMATIC SUBSTRATES; BINDING ABILITIES; BINDING CONSTANT; CALIX[4]ARENES; DEEP CAVITY; NEUTRAL SUBSTRATES; NMR SPECTROSCOPY; NMR TITRATION; TETRAAMINOCALIXARENE;

MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY;

SUBSTRATES;

EID: 69249162738     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.6.1247     Document Type: Article

References (50)

1. Gutsche, C. D. In Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998; p 50.
2. Ikeda, A.; Shinkai, S. Chem Rev. 1997, 97, 1713.
3. Bohmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713.
4. Vicens, J.; Bohmer, V. In Calixarenes: A Versatile Class of Macrocyclic Compounds; Kluwer: Dordrecht, 1991; p 127.
5. Lhotak, P.; Zieba, R.; Hromadka, V.; Stibor, I.; Sykora, J. Tetrahedron Lett. 2003, 44, 4519.
6. Oh, S. W.; Moon, J. D.; Lim, H. J.; Park, S. Y.; Kim, T.; Park, J.; Han, M. H.; Snyder, M.; Choi, E. Y.; J. Fed. A. Soc. Exp. Biol. 2005, 19, 1335.
7. Jung, H.; Song, K.; Kim, T. Bull. Korean Chem. Soc. 2007, 28, 1792.
8. Demody, D. L.; Crooks, M. R.; Kim, T. J. Am. Chem. Soc. 1996, 118, 11912.
9. Dermody, D. L.; Lee, Y.; Kim, T.; Crooks, R. M. Langmuir 1999, 15, 8435.
10. Lee, Y.; Lee, E. K.; Cho, Y. W.; Matsui, T.; Kang, I.; Kim, T.; Han, M. H. Proteomics 2003, 3, 2289.
11. Andreetti, G. D.; Ungaro, R.; Pochini, A. J. Chem. Soc. Chem. Comm. 1979, 1005.
12. Nachtigall, F. F.; Lazzarotto, M.; Nome, F. J. Braz. Chem. Soc. 2002, 13, 295.
13. Yilmaz, A.; Memon, S.; Yilmaz, M. Tetrahedron 2002, 58, 7735.
14. Chawla, H. M.; Singh, S. P. Tetrahedron 2008, 64, 741.
15. Sdira, S. B.; Felix, C.; Giudicelli, M.; Vocanson, F.; Perrin, M.; Lamartine, R. Tetrahedron Letters 2005, 46, 5659.
16. Yang, F.; Ji, Y.; Guo, H.; Lin, J.; Peng, Q. Syn. Comm. 2007, 37, 79.
17. Baklouti, L.; Cherif, J.; Abidi, R.; Arnaud-Neu, F.; Harrowfield, J.; Vicens, J. Org. Biomol. Chem 2004, 2, 2786.
18. Kang, S. O.; Nam, K. C. Bull. Korean Chem. Soc. 2002, 23, 640.
19. Baldini, L.; Sansone, F.; Casnati, A.; Ugozzoli, F.; Ungaro, R. J. Supra. Chem. 2002, 2, 219.
20. Miyaji, H.; Dudic, M.; Tucker, J. H. R.; Prokes, I.; Light, M. E.; Hursthouse, M. B.; Stibor, I.; Lhotak, P. Tetrahedron Lett. 2002, 43, 873.
21. (d) Kumar, S.; Chawla, H. M.; Varadarajan, R. Tetrahedron Lett. 2002, 43, 2495.
22. Garrier, E.; Le Gac, S. L.; Jabin, I. Tetrahedron: Asymmetry 2005, 16, 3767.
23. Chawla, H. M.; Sahu, S. M.; Shrivastava, R. Tetrahedron Letters 2007, 48, 6054.
24. Kocabas, E.; Durmaz, M.; Alpaydin, S.; Sirit, A.; Yilmaz, M. Chirality 2008, 20, 26.
25. Korbakov, N.; Timmerman, P.; Lidich, N.; Urbach, B.; Saar, A.; Yitzchaik, S. Langmuir 2008, 24, 2580.
26. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
27. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. 2001, 40, 486.
28. Masci, B.; Persiani, D.; Thuery, P. J. Org. Chem. 2006, 71, 9784.
29. Lehn, J.; Vogle, F.; MacNicol, D. D.; Davis, J. E.; Atwood, J. L. In Comprehensive Supramolecular Chemistry; Pergamon: UK, 1996; p 69.
30. Arduini, A.; Brindani, E.; Giorgi, G.; Pochini, A.; Secchi, A. Tetrahendron 2003, 59, 7587.
31. Chawla, H. M.; Pant, N.; Srivastava, B.; Upreti, S. Org. Lett. 2006, 8, 2237.
32. Chawla, H. M.; Singh, S. P.; Sahu, S. N.; Upreti, S. Tetrahedron 2006, 62, 7854.
33. Valeur, B.; Leray, I. Inorg. Chim. Acta 2007, 360, 765.
34. Petrella, A. J.; Raston, C. L. J. Organomet. Chem. 2004, 689, 4125.
35. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.
36. Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254.
37. Iqbal, M.; Mangiafico, T.; Gutsche, C. D. Tetrahedron 1987, 43, 4917.
38. Casnati, A.; Pochini, A.; Ungaro, R.; Ugozzoli, F.; Arnaud, F.; Fanni, S.; Schwing, M.; Ehberink, R. J. M.; Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 2767.
39. 2-Ar), 6.85 (s, 4H, Ar-H), 7.01 (s, 4H, Ar-H), 7.95 (s, 2H, Ar-OH).
40. 2-Ar), 6.60 (t, 2H, J = 7.14 Hz, Ar-H), 6.71 (t, 2H, J = 6.59 Hz, Ar-H), 6.88 (d, 2H, J = 7.14 ArH), 7.02 (d, 2H, J = 7.14 Ar-H), 8.28 (s, 2H, Ar-OH).
41. Shinkai, S.; Tsubaki, T.; Sone, T.; Manabe, O. Tetrahedron Letters 1985, 26, 3343.
42. Zhang, W.; Zheng, Y.; Huang, Z. Synth. Commun. 1997, 27, 3763.
43. Kumar, S.; Kurur, N. D.; Chawla, H. M.; Varadarajan, R. Synth. Commun. 2001, 31, 775.
44. Wageningen, A. M. A.; Snip, E.; Verboom. W.; Reinhoudt, D. N.; Boerrigter, H. Liebigs Ann/Recueil 1997, 2235.
45. Furnis, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell A. R. In Vogel's Text Book of Practical Organic Chemistry; Longmann: England, 1989; p 902.
46. 3): d 11.38, 23.72, 32.89, 54.76, 78.53, 113.59, 126.72, 126.89, 127.32, 128.56, 129.09, 134.50, 138.99, 139.60, 142.89, 144.19, 145.29, 146.79. MALDI-TOF MS m/z (M+): 1288.7
47. Shalley, A. C. In Analytical Methods in Supramolecular Chemistry; WILEY-VCH Verlag GmbH & Co. KGaA: Weinheim, 2007; p 39.
48. Rose, N. J.; Drago, R. S. J. Am. Chem. Soc. 1959, 81, 6138.
49. 3 were separately prepared. The 1H NMR tubes were filled with 500 μL solution of the receptor and the substrate in the following volume ratios (all in μL): 50:450, 100:400, 150:350, 200:300, 250:250, 300:200, 350:150, 400:100, 450:50.
50. Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815.