Experimental and computational studies of anion recognition by pyridine-functionalised calixarenes

References

• (a) Beer, P.D.; Gale, P.A. Angew. Chem. Int. Ed. 2001, 40, 486–516. (b) Gale, P.A.; Garcia Garrido, S.E.; Garric, J. Chem. Soc. Rev. 2008, 37, 151–190; (c) Gunnlaugsson, T.; Glynn, M.; Tocci, G.M.; Kruger, P.E.; Pfeffer, F.M. Coord. Chem. Rev. 2006, 250, 3094–3117; (d) Hua, Y.; Flood, A.H. Chem. Soc. Rev. 2010, 39, 1262–1271; (e) Kubik, S. Chem. Soc. Rev. 2009, 38, 585–605; (f) Llinares, J.M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57–75; (g) Martinez-Manez, R.; Sancenon, F. Coord. Chem. Rev. 2006, 250, 3081–3093; (h) O'Neil, E.J.; Smith, B.D. Coord. Chem. Rev. 2006, 250, 3068–3080; (i) Perez, J.; Riera, L. Chem. Soc. Rev. 2008, 37, 2658–2667; (j) Rice, C.R. Coord. Chem. Rev. 2006, 250, 3190–3199; (k) Sessler, J.L.; Gale, P.A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, 2006; (l) Sharma, K.; Cragg, P.J. Chem. Sens. 2011, 1, 9/1–9/18; (m) Steed, J.W. Chem. Soc. Rev. 2009, 38, 506–519
   Google Scholar
• (a) Hargrove, A.E.; Nieto, S.; Zhang, T.; Sessler, J.L.; Anslyn, E.V. Chem. Rev. 2011, 111, 6603–6782; (b) Katayev, E.A.; Ustynyuk, Y.A.; Sessler, J.L. Coord. Chem. Rev. 2006, 250, 3004–3039
   Google Scholar
• (a) Gutsche, C.D., Ed. Calixarenes: An Introduction, 2nd ed.; Royal Society of Chemistry: Cambridge, 2008; (b) Matthews, S.E.; Beer, P.D. Supramol. Chem. 2005, 17, 411–435; (c) Shokova, E.A.; Kovalev, V.V. Russ. J. Org. Chem. 2009, 45, 1275–1314; For lower rim di- or tetra-substituted calixarenes used for anion recognition, see: (d) Joseph, R.; Rao, C.P. Chem. Rev. 2011, 111, 4658–4702; With amido moieties, see: (e) Ben, S.S.; Felix, C.; Giudicelli, M.-B.; Vocanson, F.; Perrin, M.; Lamartine, R. Tetrahedron Lett. 2005, 46, 5659–5663; (f) Cherif, J.K.; Mahouachi, M.; Abidi, R.; Vicens, J. J. Inclusion Phenom. Macrocyclic Chem. 2006, 55, 51–57; (g) Kendi, B.; Naziroglu, H.N.; Yilmaz, M.; Sirit, A. J. Macromol. Sci. Part A Pure Appl. Chem. 2010, 47, 225–229; With urea and thiourea moieties, see: (h) Metay, E.; Duclos, M. C.; Pellet-Rostaing, S.; Lemaire, M.; Kannappan, R.; Bucher, C.; Saint-Aman, E.; Chaix, C. Tetrahedron 2009, 65, 672–676; (i) Metay, E.; Duclos, M.C.; Pellet-Rostaing, S.; Lemaire, M.; Schulz, J.; Kannappan, R.; Bucher, C.; Saint-Aman, E.; Chaix, C. Supramol. Chem. 2009, 21, 68–80; (j) Schazmann, B.; Diamond, D. New J. Chem. 2007, 31, 587–592; (k) Scheerder, J.; Fochi, M.; Engbersen, J.F.J.; Reinhoudt, D.N. J. Org. Chem. 1994, 59, 7815–7820; (l) Zlatuskova, P.; Stibor, I.; Tkadlecova, M.; Lhotak, P. Tetrahedron 2004, 60, 11383–11390; (m) Quinlan, E.; Matthews, S.E.; Gunnlaugsson, T. Tetrahedron Lett. 2006, 47, 9333–9338; (n) Quinlan, E.; Matthews, S.E.; Gunnlaugsson, T. J. Org. Chem. 2007, 72, 7497–7503
   Google Scholar
• (a) Kilah, N.L.; Beer, P.D. Top. Heterocycl. Chem. 2010, 24, 301–340; (b) Molard, Y.; Parrot-Lopez, H. Tetrahedron Lett. 2001, 42, 4799–4802; (c) Spencer, D.J.E.; Johnson, B.J.; Johnson, B.J.; Tolman, W.B. Org. Lett. 2002, 4, 1391–1393
   Google Scholar
• (a) Chen, L.; Zhang, J.; Zhao, W.; He, X.; Liu, Y. J. Electroanal. Chem. 2006, 589, 106–111; (b) Colleran, J.J.; Creaven, B.S.; Donlon, D.F.; McGinley, J. Dalton Trans. 2010, 39, 10928–10936; (c) Joseph, R.; Ramanujam, B.; Acharya, A.; Khutia, A.; Rao, C.P. J. Org. Chem. 2008, 73, 5745–5758; (d) Liu, Y.; Zhao, B.-T.; Chen, L.-X.; He, X.-W. Microchem. J. 2000, 65, 75–79; (e) Casnati, A.; Della, C.N.; Fontanella, M.; Sansone, F.; Ugozzoli, F.; Ungaro, R.; Liger, K.; Dozol, J.-F. Eur. J. Org. Chem. 2005, 2338–2348; (f) Danil de Namor, A.F.; Aguilar-Cornejo, A.; Soualhi, R.; Shehab, M.; Nolan, K.B.; Ouazzani, N.; Mandi, L. J. Phys. Chem. B 2005, 109, 14735–14741; (g) Liu, Y.; Zhao, B.-T.; Zhang, H.-Y.; Ju, H.-F.; Chen, L.-X.; He, X.-W. Helv. Chim. Acta 2001, 84, 1969–1975
   Google Scholar
• Stoikov , I.I. , Zhukov , A.Y. , Agafonova , M.N. , Sitdikov , R.R. , Antipin , I.S. and Konovalov , A.I. 2010 . Tetrahedron , 66 : 359 – 367 .
   Web of Science ®Google Scholar
• (a) Tabakci, M.; Memon, S.; Yilmaz, M. Tetrahedron 2007, 63, 6861–6865; (b) Tabakci, M.; Memon, S.; Yilmaz, M.; Roundhill, D.M. J. Inclusion Phenom. Macrocyclic Chem. 2003, 45, 265–270; (c) Yigiter, S.; Bayrakci, M.; Ertul, S.; Yilmaz, M. J. Appl. Polym. Sci. 2012, 124, 3831–3839; (d) Sayin, S.; Ozcan, F.; Yilmaz, M. Desalination 2010, 262, 99–105; (e) Yilmaz, A.; Tabakci, B.; Akceylan, E.; Yilmaz, M. Tetrahedron 2007, 63, 5000–5005
   Google Scholar
• Beer , P.D. , Drew , M.G.B. and Gradwell , K. 2000 . Perkin , 2 : 511 – 519 .
   Google Scholar
• Rudkevich , D.M. , Verboom , W. and Reinhoudt , D.N. 1994 . J. Org. Chem. , 59 : 3683 – 3686 .
   Web of Science ®Google Scholar
• (a) Mayo, K.H.; Hoye, T.R.; Chen, X.; Regents of the University of Minnesota WO2006042104A2, 2006; p. 115; (b) Chen, X.; Dings, R.P.M.; Nesmelova, I.; Debbert, S.; Haseman, J.R.; Maxwell, J.; Hoye, T.R.; Mayo, K.H. J. Med. Chem. 2006, 49, 7754–7765; A compound very similar to 6 has been reported with t-butyl groups at the upper rim. See (c) van der Veen, N.J.; Flink, S.; Deij, M.A.; Egberink, R.J.M.; van Veggel, F.C. J.M.; Reinhoudt, D.N. J. Am. Chem. Soc. 2000, 122, 6112–6113. Compound 5. No characterisation of this compound is given in the paper
   Google Scholar
• Zhang , S. , Palkar , A. and Echegoyen , L. 2006 . Langmuir , 22 : 10732 – 10738 .
   PubMed Web of Science ®Google Scholar
• Mohamadi , F. , Richards , N.G.J. , Guida , W.C. , Liskamp , R. , Lipton , M. , Caufield , C. , Chang , G. , Hendrickson , T. and Still , W.C. 1990 . J. Comput. Chem. , 11 : 440 – 467 .
   Web of Science ®Google Scholar
• (a) Beer, P.D.; Timoshenko, V.; Maestri, M.; Passaniti, P.; Balzani, V. Chem. Commun. 1999, 1755–1756; (b) McGinley, J.; McKee, V.; Walsh, J.M.D. Inorg. Chim. Acta 2011, 375, 57–62
   Google Scholar
• (a) Job, P. Ann. Chim. Appl. 1928, 9, 113–203; (b) MacCarthy, P. Anal. Chem. 1978, 50, 2165
   Google Scholar
• Hynes , M.J. 1993 . J. Chem. Soc. Dalton Trans. , : 311 – 312 .
   Google Scholar