Metal-assembled cobalt(II) resorc[4]arene-based cage molecules that reversibly capture organic molecules from water and act as NMR shift reagents

Inorganic Chemistry

Volumn 39, Issue 4, 2000, Pages 783-790

  Fox, O Danny ^a,b   Leung, Jenny F Y ^a   Hunter, Jesse M ^a   Dalley, N Kent ^a   Harrison, Roger G ^a  

^a Brigham Young University   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEX; WATER;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0034695868     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic991235i     Document Type: Article

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38. 8- either with or without an included guest molecule. Others also have experienced challenges. (a) Whiteford, J. A.; Rachlin, E. M.; Stang, P. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 169. (b) Leize, E.; Van Dorddelaer, A.; Kramer, R.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 990. (c) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (d) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155 and references therein.
39. 8- either with or without an included guest molecule. Others also have experienced challenges. (a) Whiteford, J. A.; Rachlin, E. M.; Stang, P. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 169. (b) Leize, E.; Van Dorddelaer, A.; Kramer, R.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 990. (c) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (d) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155 and references therein.
40. 8- either with or without an included guest molecule. Others also have experienced challenges. (a) Whiteford, J. A.; Rachlin, E. M.; Stang, P. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 169. (b) Leize, E.; Van Dorddelaer, A.; Kramer, R.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 990. (c) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (d) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155 and references therein.
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44. For a discussion of predicted hydrogen signals for the different possible isomers, see Supporting Information. See Supporting Information for a table of chemical shifts, peak assignments, and a labeled structural drawing.
45. 1 values.
46. 1 values for both benzylic and acetate protons and their similar chemical shifts, the peak assignments for these protons are tentative.
47. We initially placed the encapsulated water molecules outside the cavity, but through symmetry they are found to be within the cavity. Water molecules have previously been found within resorc[4]arene container molecules, both in mass spectrometric and X-ray studies, although this is not a frequently encountered phenomenon. (a) Choi, H.-J.; Buhring, D.; Quan, M. L. C.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1992, 1733. (b) Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 111.
48. We initially placed the encapsulated water molecules outside the cavity, but through symmetry they are found to be within the cavity. Water molecules have previously been found within resorc[4]arene container molecules, both in mass spectrometric and X-ray studies, although this is not a frequently encountered phenomenon. (a) Choi, H.-J.; Buhring, D.; Quan, M. L. C.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1992, 1733. (b) Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 111.
49. 8- in a manner similar to the that in low-temperature hydrogen NMR experiments.
50. 1H NMR chemical shift changes. When N-benzyliminodiacetic acid or iminodiacetic acid is added to an aqueous solution of CoCh and organic molecules in a manner similar to that for the resorc[4]arene ligand, no change in proton resonances is observed and no new signals for organic molecules are observed.