Molecular recognition of ammonium ion by tetrahomodioxacalix[4]biscrown

Tetrahedron Letters

Volumn 48, Issue 8, 2007, Pages 1327-1330

  Hong, Jooyeon ^a   Song, Jongwon ^a   Ham, Sihyun ^a  

^a Sookmyung Women's University   (South Korea)

Author keywords

Calix 4 biscrown; DFT calculation; Molecular recognition

Indexed keywords

AMMONIA; CALIXARENE;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; CONFORMATION; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; GEOMETRY; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; MOLECULAR STABILITY; SIMULATION;

EID: 33846351887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.127     Document Type: Article

References (32)

1. Gutsche C.D. Calixarenes (1989), Royal Society of Chemistry, Cambridge
2. In: Vicens J., and Böhmer V. (Eds). Calixarenes: A Versatile Class of Macrocyclic Compounds (1991), Kluwer, Dordrecht
3. Gutsche C.D., Dhawan B., No K.H., and Muthukrishnan R. J. Am. Chem. Soc. 103 (1981) 3782
4. Dhawan B., and Gutsche C.D. J. Org. Chem. 48 (1983) 1536
5. Gutsche C.D., and Bauer L.J. J. Am. Chem. Soc. 107 (1985) 6059
6. Masci B., and Saccheo S. Tetrahedron 49 (1993) 10739
7. De Iasi G., and Masci B. Tetrahedron Lett. 34 (1993) 6635
8. Masci B. Tetrahedron 51 (1995) 5459
9. Masci B., Finelli M., and Varrone M. Chem. Eur. J. 4 (1998) 2018
10. Thuèry P., Nierlich M., Vicens J., Masci B., and Takemura H. Eur. J. Inorg. Chem. (2001) 637
11. Thuèry P., Nierlich M., Vicens J., and Masci B. Acta Crystallogr., Sect. C 57 (2001) 70
12. No K., Lee J.H., Yang S.H., Kim M.J., and Kim J.S. J. Org. Chem. 67 (2002) 3165
13. No K.H. Bull. Korean Chem. Soc. 20 (1999) 33
14. No K.H., Park Y.J., and Choi E.J. Bull. Korean Chem. Soc. 20 (1999) 905
15. Masci B. J. Org. Chem. 66 (2001) 1497
16. No K., Kim J.S., Shon O.J., Yang S.H., Suh I.H., Kim J.G., Bartsch R.A., and Kim J.Y. J. Org. Chem. 66 (2001) 5976
17. Masci B., Gabrielli M., Mortera S.L., Nierlich M., and Thuèry P. Polyhedron 21 (2002) 1125
18. No K., Chung H.J., Yu H.J., Yang S.H., Noh K.H., Thuery P., Vicens J., and Kim J.S. J. Inclusion Phenom. Macro. Chem. 46 (2003) 97
19. No K., Bok J.H., Suh I.H., Kang S.O., Ko J., Nam K.C., and Kim J.S. J. Org. Chem. 69 (2004) 6938
20. Choi J.K., Lee A., Kim S., Ham S., No K., and Kim J.S. Org. Lett. 8 (2006) 1601
21. Demura M., Yoshida T., Hirokawa T., Kumaki Y., Aizawa T., Nitta K., Bitter I., and Toth K. Bioorg. Med. Chem. Lett. 15 (2005) 1367
22. Choe J.-I., Kim K., and Chang S.-K. Bull. Korean Chem. Soc. 21 (2000) 465
23. Fraternali F., and Wipff G. An. Quim. Int. Ed. 93 (1997) 376
24. Ham S. Bull. Korean Chem. Soc. 25 (2004) 1911
25. * level.
26. Case D.A., Pearlman D.A., Caldwell J.W., et al. amber 7 (2002), University of California, San Francisco
27. Dewar M., and Thiel W. J. Am. Chem. Soc. 99 (1977) 4499
28. Dewar M., Zoebisch E.G., and Healy E.F. J. Am. Chem. Soc. 107 (1985) 3902
29. Becke A.D. J. Chem. Phys. 98 (1993) 5648
30. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K., Burant J.C., Millam J.M., Iyengay S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Comperts R., Startmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenbuerg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chem W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
31. The binding energy was calculated as the following equation. BE = E(complex) - {E(host) + E(ammonium ion)}.
32. The exo- and endo-complex of 6 are drawn in Figure S1 in Supplementary data.