Recognition of Anions by Protonated Methylazacalixpyridines

doi:10.1007/s11458-009-0094-8

Front. Chem. China

2009, Vol. 4

Issue (3) : 307-312 https://doi.org/10.1007/s11458-009-0094-8

Research articles

Recognition of Anions by Protonated Methylazacalixpyridines

Hanyuan GONG , Dexian WANG , Zhitang HUANG , Meixiang WANG ,

Beijing National Laboratory for Molecular Sciences, CAS Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;

Download: PDF(301 KB)
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Methylazacalixpyridines are a unique kind of macrocyclic molecules that are able to self-regulate their conformations to best fit the guests. They had shown good recognition to both neutral molecules such as diols and fullerenes and cations. After protonation, the conformation of methylazacalixpyridines became more flexible and could serve as receptors for anions. In the solution, the protonated methylazacalix[2]pyridine[2]arene formed complexes with halides yielding biding constants of 79 (mol/L)^−1 for chloride, 10 (mol/L)^−1 for bromide, and 79 (mol/L)^−1 for iodide, respectively. The crystal structures of the complexes between protonated methylazacalix[4]pyridine (MACP-4), methylazacalix[2]pyridine[2]arene (MACP-2-A-2), and iodide anion showed a multiple interaction mode including electrostatic attraction, hydrogen bonding, and anion-p interactions.

Keywords anion recognition methylazacalixpyridine protonation

Issue Date: 05 September 2009

Cite this article:

Hanyuan GONG,Dexian WANG,Zhitang HUANG, et al. Recognition of Anions by Protonated Methylazacalixpyridines[J]. Front. Chem. China, 2009, 4(3): 307-312.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0094-8
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I3/307

	Supramolecular Chemistry of Anions, (Eds: A. Bianchi, K, Bowman-James, E. Garcia-Espana), Wiley-VCH: New York, NY, 1997
	Anion Sensing (Ed: I. Stibor) in Top. Curr. Chem. 2005, 255, pp 1―299.
	Recognition of Anions (Ed: Ramón V.) in Structure and Bonding (Ed: Mingos D.M.P.), Springer, 2008, 129, pp 1―249
	Lee, C. H.; Miyaji, H.; Yoon, D. W.; Sessler, J. L., Chem. Commun. 2008, 24 doi: 10.1039/b713183f
	Gale, P. A.; Garcia-Garrido, S.E.; Garric, J., Chem.Soc. Rev. 2008, 37, 151 doi: 10.1039/b715825d
	Davis, A. P.; Sheppard, D. N.; Smith, B. D., Chem. Soc. Rev. 2007, 36, 348 doi: 10.1039/b512651g
	Pascal, R. A.; Spergel, J.; Engbersen, D. V., TetrahedronLett. 1986, 27, 4099 doi: 10.1016/S0040-4039(00)84920-5
	Valiyaveettil, S.; Engbersen, J. F.J.; Verboom, W.; Reinhoudt, D. N., Angew. Chem. 1993, 105, 942 doi: 10.1002/ange.19931050635
	Valiyaveettil, S.; Engbersen, J. F.J.; Verboom, W.; Reinhoudt, D. N., Angew. Chem. Int. Ed. Engl. 1993, 32, 900 doi: 10.1002/anie.199309001
	Bisson, A. P.; Lynch, V. M.; Monahan, M. K. C.; Anslyn, E. V., Angew. Chem. 1997, 109, 2435 doi: 10.1002/ange.19971092115
	Bisson, A. P.; Lynch, V. M.; Monahan, M. K. C.; Anslyn, E. V., Angew. Chem. Int. Ed. Engl. 1997, 36, 2340 doi: 10.1002/anie.199723401
	Kelley, T. R.; Kim, M. G., J. Am. Chem. Soc. 1994, 116, 7072 doi: 10.1021/ja00095a009
	Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V., J. Am. Chem. Soc. 1996, 118, 5140 doi: 10.1021/ja960307r
	Schmidtchen, F. P., Angew. Chem. 1977, 89, 751 doi: 10.1002/ange.19770891024
	Schmidtchen, F. P., Angew. Chem. Int. Ed. Engl. 1977, 16, 720 doi: 10.1002/anie.197707201
	Schmidtchen, F. P., Chem. Ber. 1980, 113, 864 doi: 10.1002/cber.19801130308
	Worm, K.; Schmidtchen, F. P., Angew. Chem. 1995, 107, 71 doi: 10.1002/ange.19951070112
	Worm, K.; Schmidtchen, F. P., Angew. Chem. Int. Ed. Engl. 1995, 34, 65 doi: 10.1002/anie.199500651
	Yang, X.; Knobler, C. B.; Hawthorne, M. F., Angew.Chem. 1991, 103, 1519 doi: 10.1002/ange.19911031125
	Yang, X.; Knobler, C. B.; Hawthorne, M. F., Angew.Chem. Int. Ed. Engl. 1991, 304, 1507 doi: 10.1002/anie.199115071
	Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L. H.?; Shen, B. J.; Jin, D. S., J. Am. Chem. Soc. 1993, 115, 475 doi: 10.1021/ja00055a017
	Mascal, M.; Armstrong, A.; Bartberger, M. D., J. Am.Chem. Soc. 2002, 124, 6274 doi: 10.1021/ja017449s
	Quiñonero, D.; Garau, C.; Rotger, C.; Frontera, A.; Ballester, P.; Costa, A.; Deyà, P. M., Angew. Chem. Int. Ed. 2002, 41, 3389
	Rosokha, Y. S.; Lindeman, S. V.; Rosokha, S. V.; Kochi, J. K., Angew. Chem. Int. Ed. 2004, 43, 4650 doi: 10.1002/anie.200460337
	Berryman, O. B.; Bryantsev, V. S.; Stay, D. P.; Johnson, D. W.; Hay, B. P., J. Am. Chem. Soc. 2007, 129, 48 doi: 10.1021/ja063460m
	Wang, D. X.; Zheng, Q. Y.; Wang, Q.Q.; Wang, M.X., Angew. Chem. Int. Ed. 2008, 47, 7485 doi: 10.1002/anie.200801705
	Wang, M. X.; Yang, H. B., J. Am. Chem. Soc. 2004, 126, 15412 doi: 10.1021/ja0465092
	Katz, J. L.; Feldman, M. B.; Conry, R. R., Org. Lett. 2005, 7, 91 doi: 10.1021/ol047840t
	Katz, J. L.; Selby, K. J.; Conry, R. R., Org. Lett. 2005, 7, 3505 doi: 10.1021/ol051180q
	Katz, J. L.; Geller, B. J.; Conry, R. R., Org. Lett. 2006, 8, 2755 doi: 10.1021/ol060823e
	Maes, W.; Van Rossom, W.; Van Hecke, K.; Van Meervelt, L.; Dehaen, W., Org. Lett. 2006, 8, 4161 doi: 10.1021/ol0617446
	Hao, E.; Fronczek, F. R.; Vicente, M. G. H., J. Org.Chem. 2006, 71, 1233 doi: 10.1021/jo051964h
	Chambers, R. D.; Hoskin, P. R.; Kenwright, A. R.; Khalil, A.; Richmond, P.; Sandford, G.; Yufit, D. S.; Howard, J. A. K., Org. Biomol. Chem. 2003, 2137 doi: 10.1039/b303443g
	Chambers, R. D.; Hoskin, P. R.; Khalil, A.; Richmond, P.; Sandford, G.; Yufit, D. S.; Howard, J. A. K., J. Fluorine. Chem. 2002, 116, 19 doi: 10.1016/S0022-1139(02)00071-4
	Li, X. H.; Upton, T. G.; Gibb, C. L. D.; Gibb, B. C., J. Am. Chem. Soc. 2003, 125, 650 doi: 10.1021/ja029116g
	Yang, F.; Yan L. W.; Ma, K. Y.; Yang, L.; Li, J. H.; Chen, L. J.; You, J. S, Eur. J. Org. Chem. 2006, 1109 doi: 10.1002/ejoc.200500879
	Wang, Q. Q.; Wang, D. X.; Ma, H. W.; Wang, M. X., Org. Lett. 2006, 8, 5967 doi: 10.1021/ol062441e
	Wang, Q. Q.; Wang, D. X.; Zheng, Q. Y.; Wang, M. X., Org. Lett. 2007, 9, 2847 doi: 10.1021/ol0710008
	Hou, B. Y.; Zheng, Q. Y.; Wang, D. X.; Huang, Z. T.; Wang, M. X., Chem. Commun. 2008, 3864 doi: 10.1039/b805293j
	Ito, A.; Ono, Y.; Tanaka, K., New J. Chem. 1998, 779 doi: 10.1039/a804229b
	Ito, A.; Ono, Y.; Tanaka, K., J. Org. Chem. 1999, 64, 8236 doi: 10.1021/jo990983m
	Miyazaki, Y.; Kanbara, T.; Yamamoto, T., Tetrahedron Lett. 2002, 43, 7945 doi: 10.1016/S0040-4039(02)01842-7
	Wang, M. X.; Zhang, X. H.; Zheng, Q. Y., Angew. Chem. Int. Ed. 2004, 43, 838 doi: 10.1002/anie.200351975
	Gong, H. Y.; Zhang, X. H.; Wang, D. X.; Ma, H. W.; Zheng, Q. Y.; Wang, M. X., Chem. Eur. J. 2006, 12, 9262 doi: 10.1002/chem.200600377
	Gong, H. Y.; Zheng, Q. Y.; Zhang, X. H.; Wang, D. X.; Wang, M. X., Org. Lett. 2006, 8, 4895 doi: 10.1021/ol061928k
	Gong, H. Y.; Wang, D. X.; Xiang, J. F.; Zheng, Q. Y.; Wang, M. X., Chem. Eur. J. 2007, 13, 7791 doi: 10.1002/chem.200700498
	Liu, S. Q.; Wang, D. X.; Zheng, Q. Y.; Wang, M. X. Chem. Commun. 2007, 3856 doi: 10.1039/b705595a
	Zhang, E. X.; Wang, D. X.; Zheng, Q. Y.; Wang, M. X., Org. Lett. 2008, 10, 2565 doi: 10.1021/ol800840m
	Tsue, H.; Ishibashi, K.; Takahashi, H.; Tamura, R., Org. Lett. 2005, 7, 2165 doi: 10.1021/ol050493i
	Fukushima, W.; Kanbara, T.; Yamamoto, T., Synlett2005, 2931
	Selby, T. D.; Blackstock, S. C., Org. Lett. 1999, 1, 2053 doi: 10.1021/ol991040e
	Suzuki, Y.; Yanagi, T.; Kanbara, T.; Yamamoto, T., Synlett, 2005, 263
	Gutsche, C. D., The Royal Society of Chemistry, Cambridge, 1989
	Gutsche, C. D., Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998
	Calixarenes in Action(Eds.: L. Mandolini, Ungaro, R.), Imperial College Press, London, 2000; d) Calixarenes 2001 (Eds.: Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J.; M. Saadioui), Kluwer Academic Publishers, TheNetherlands, 2001
	Gale, P. A.; Anzenbacher, P.; Sessler, J. L., Coord. Chem. Rev. 2001, 222, 57 doi: 10.1016/S0010-8545(01)00346-0
	Sliwa, W., Heterocycles2002, 57, 169 doi: 10.3987/REV-01-544
	Král, V.; Gale, P. A.; Anzenbacher, P.; Jursiková, K.; Lynch, V.; Sessler, J. L., Chem. Commun. 1998, 9
	Sessler, J. L.; Cho, W. S.; Lynch, V.; Král, V., Chem. Eur. J. 2002, 8, 1134 doi: 10.1002/1521-3765(20020301)8:5<1134::AID-CHEM1134>3.0.CO;2-M
	Newkome, G. R.; Joo, Y. J.; Fronczek, F. R., J. Chem. Soc. Chem. Commun. 1987, 854 doi: 10.1039/c39870000854
	Crystallographic data for MACP-4·2HI·4I₂ (C₂₄H₂₆I₁₀N₈): Mr = 1695.53, Tetragonal, space group P42/nmc, a = 13.5529(19), b = 13.5529(19), c =10.743(2) Å, α = 90.00°, β = 90.00°, γ = 90.00°, V = 1973.2(5) Å³, T = 293(2)?K, full-matrix least-squaresrefinement on F² converged to R_F = 0.0183 [I > 2σ(I)], 0.0.0321 (all data) and Rw(F²) = 0.0535 [I > 2σ(I)], 0.0645 (all data), goodness of fit 0.420. Crystallographic datafor MACP-2-A-2·2HI·I₂·CH₃OH (C₂₇H₃₂I₄N₆O): Mr = 964.19, Triclinic, space group P-1, a = 9.1832(18), b =11.184(2), c = 16.038(3) Å, α = 97.71°, β = 92.98°, γ = 91.33°, V = 1629.3(6) Å³, T = 293(2) K,full-matrix least-squares refinement on F² converged to R_F = 0.0414 [I > 2σ(I)], 0.0507 (all data) and Rw(F²) = 0.1304 [I >2σ(I)], 0.1373 (all data), goodness of fit 1.063

Viewed

Full text

Abstract

Cited

Shared

Discussed