Abstract
A system of molecular architecture that consists of fused 6-membered carbocyclic and heterocyclic rings and orients heteratom binding sites toward a molecular cavity or cleft has been developed in our laboratories at SUNY Stony Brook and the University of Nevada. This approach was initially used to produce torands (e.g., 1, Figure 1) that form exceptionally strong complexes with metal cations.1–11 Butyl substituents, arising from the 9-n-butyloctahydroacridine building block,12 were incorporated into the design of these metal complexing agents in order to enhance their solubilities in organic solvents.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Bell, T.W. and Firestone, A. (1986) Torands: Rigid toroidal macrocycles. Calcium sequestration by a member of this new ligand class, J. Am. Chem. Soc. 108, 8109–8111.
Bell, T.W., Firestone, A., Hu, L.-Y. and Guzzo, F. (1987) Torands: Planar polyazamacrocyclic ligands for metal ions, J. Inclusion Phenomena 5, 149–152.
Bell, T.W., Firestone, A. and Ludwig, R. (1989) Exceptionally stable alkali metal complexes of a torand, J. Chem. Soc., Chem. Commun., 1902-1904.
Bell, T.W. and Liu, J. (1990) Torand synthesis by trimerization — new receptors for guanidinium, Angew. Chem., 102, 931–933; (1990) Angew. Chem. Intl. Ed. Engl., 29, 923-925.
Bell, T.W., Cragg, P.J., Drew, M.G.B., Firestone, A. and Kwok, D.-I.A. (1992) Conformational preference of the torand ligand in its complexes with potassium and rubidium picrate, Angew. Chem. 104, 319; (1992) Angew. Chem. Intl. Ed. Engl. 31, 345-347.
Bell, T.W., Cragg, P.J., Drew, M.G.B., Firestone, A. and Kwok, D.-I.A. (1992) A supramolecular assembly of two torands, two lithium ions and three water molecules, Angew. Chem. 104, 321; (1992) Angew. Chem. Intl. Ed. Engl. 31, 348-350.
Bell, T.W. (1992) From crowns to torands and beyond, in S.R. Cooper (ed.), Crown Compounds: Toward Future Applications, VCH Publishers: New York, 305–318.
Bell, T.W., Cragg, P.J., Drew, M.G.B., Firestone, A., Kwok, D.-I.A., Liu, J., Ludwig, R.T. and Papoulis, A.T. (1993) Synthesis of new torands and new uses for old torands, Pure and Applied Chem. 65, 361–366.
Boguslavsky, L. and Bell, T.W. (1994) Cation response of torand thin films at the air-water interface, Langmuir 10, 991–993.
Bell, T.W., Heiss, A.M., Jousselin, H. and Ludwig, R.T. (1995) Toward columns and channels from torands and molecular coils, in J.S. Siegel (ed.), Supramolecular Stereochemistry, Kluwer: Dordrecht, The Netherlands, 161–168.
Bell, T.W. and Tidswell, J. (1996) Torands, in D. Parker (ed.), Macrocycle Synthesis: A Practical Approach, Oxford University Press: Oxford, 119–143.
Bell, T.W., Cho, Y.-M., Firestone, A., Healy, K., Liu, J., Ludwig R.T. and Rothenberger, S.D. (1993) 9-n-Butyl-1,2,3,4,5,6,7,8-octahydroacridin-4-ol, in J.P. Freeman (ed.), Organic Syntheses, Collective Volume VIII, Wiley Books: New York, 1993, 87–93.
Catalán, J., Gómez, J., Couto, A. and Laynez, J. (1990) Toward a solvent basicity scale: The calorimetry of the pyrrole probe, J. Am. Chem. Soc. 112, 1678–1681.
Bell, T.W. and Liu, J. (1988) Hexagonal lattice hosts for urea. A new series of designed heterocyclic receptors, J. Am. Chem. Soc. 110, 3673–3674.
Bell, T.W., Firestone, A., Liu, J., Ludwig, R. and Rothenberger, S.D. (1990) The hexagonal lattice approach to molecular receptors, in J.L. Atwood (ed.), Inclusion Phenomena and Molecular Recognition, Plenum: New York, 49–56.
Bell, T.W. and Santora, V.J. (1992) Complexation of benzamidinium by anew family of artificial receptors,” J. Am. Chem. Soc. 114, 8300–8302.
Beckles, D.L., Maioriello, J., Santera, V.J., Bell, T.W., Chapoteau, E., Czech, B.P. and Kumar, A. (1995) Complexation of creatinine by synthetic receptors, Tetrahedron 51, 363–376.
Bell, T.W., Hou, Z., Luo, Y., Drew, M.G.B., Chapoteau, E., Czech, B.P. and Kumar, A. (1995) Detection of creatinine by a designed receptor, Science 269, 671–674.
Bell, T.W., Hou, Z., Zimmerman, S.C. and Thiessen, P.A. (1995) Highly effective hydrogen-bonding receptors for guanine derivatives, Angew. Chem. 107, 2321–2324; (1995) Angew. Chem. Intl. Ed. Engl. 34, 2163-2165.
van Straaten-Nijenhuis, W.F., de Jong, F., Reinhoudt, D.N., Thummel, R.P., Bell, T.W. and Liu, J. (1993) Urea transport through supported liquid membranes using synthetic carriers, J. Membrane Sci. 82, 277–283.
Cram, D.J. (1986) Preorganization — from solvents to spherands, Angew. Chem. 25, 1039–1134.
Jorgensen, W.L. and Pranata, J. (1990) Importance of secondary interactions in triply hydrogen bonded complexes: Guanine—cytosine vs uracil—2,6-diaminopyridine, J. Am. Chem. Soc. 112, 2008–2010.
Bell, T.W., Beckles, D.L., Cragg, P.J., Liu, J., Maioriello, J., Papoulis, A.T. and Santera, V.J. (1993) Intrinsic chromophores and fluorophores in synthetic molecular receptors, in A. Czarnik (ed.), Fluorescent Chemosensors of Ion and Molecule Recognition, ACS Books: Washington (D.C.) 85–103.
Free, H.M. (ed.) (1991) Modern Urine Chemistry, Miles, Inc., Elkhart, IN.
Butler, A.R. and Glidewell, C. (1985) Creatinine: an examination of its structure and some of its reactions by synergistic use of MNDO calculations and nuclear magnetic resonance spectroscopy, J. Chem. Soc., Perkin Trans. II, 1465–1467
Du Pré, S. and Mendel, H. (1955) The crystal structure of creatinine, Acta Cryst. 8, 311–313.
Král, V. and Sessler, J.L. (1995) Molecular recognition via base-pairing and phosphate chelation. Ditopic and tritopic sapphyrin-based receptors for the recognition and transport of nucleotide monophosphates, Tetrahedron 51, 539–554.
Schiessl, P. and Schmidtchen, F.P. (1994) Binding of phosphates to abiotic hosts in water, J. Org. Chem. 59, 509–511.
van Staveren, C.J., van Eerden, J., van Veggel, F.C.J.M., Harkema, S. and Reinhoudt, D.N. (1988) Cocomplexation of neutral guests and electrophilic metal cations in synthetic macrocyclic hosts, J. Am. Chem. Soc. 110, 4994–5008.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Bell, T.W., Hou, Z. (1997). Hydrogen Bonding Chemosensors for Metabolites and Nucleotides. In: Desvergne, J.P., Czarnik, A.W. (eds) Chemosensors of Ion and Molecule Recognition. NATO ASI Series, vol 492. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3973-1_9
Download citation
DOI: https://doi.org/10.1007/978-94-011-3973-1_9
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-5759-2
Online ISBN: 978-94-011-3973-1
eBook Packages: Springer Book Archive