Abstract
Significant π-π interaction is found in the complexes of (S, S)-dimethylpyridino-18-crown-6 with (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate. This finding is supported by the1H NOESY NMR spectral technique, greater chemical shift changes of aromatic protons in both host and guest molecules upon complexation, and by molecular mechanics calculations. Because of the flexibility of the ligand, the tripod hydrogen bonding causes13C relaxation times of all periphery carbons to decrease without significant selectivity. Rotational energy barrier calculations of the methyl groups of the complexed ligand also show that the (S, S)-host-(R)-guest is the more stable complex.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E.P. Kyba, M.G. Siegel, L.R. Sousa, G.D.Y. Sogah and D.J. Cram:J. Am. Chem. Soc. 95, 2691 (1973).
E.P. Kyba, K. Koga, L.R. Sousa, M.G. Siegel and D.J. Cram:J. Am. Chem. Soc. 95, 2692 (1973).
J.F. Stoddart, inProgress in Macrocyclic Chemistry, Vol. 2, eds. R.M. Izatt and J.J. Christensen, Wiley-Interscience, New York (1982) pp. 173–250.
S.T. Jolley, J.S. Bradshaw and R.M. Izatt:J. Heterocycl. Chem. 19, 3 (1982).
J.F. Stoddart, inTopics in Stereochemistry, Vol. 17, eds. E.L. Eliel and S.H. Wilen, Wiley-Interscience, New York (1988).
J.S. Bradshaw, P. Huszthy, C.W. McDaniel, M. Oue, C.-Y. Zhu, R.M. Izatt and S. Lifson:J. Coord. Chem. (B) 27, 105 (1992).
R.M. Izatt, C.-Y. Zhu, P. Huszthy and J.S. Bradshaw: ‘Enantiomeric Recognition in Macrocycle-Primary Ammonium Cation Systems’ inCrown Ethers: Toward Future Application, ed. S.R. Cooper, VCH Press, New York, 1993.
R.M. Izatt, C.-Y. Zhu, T.-M. Wang, P. Huszthy, J. Hathaway, X.-X. Zhang, J.C. Curtis and J.S. Bradshaw:J.. Incl. Phenom., in press.
d.J. Cram, R.C. Helgeson, L.R. Sousa, J.M. Timko, M.L.A. Domeier, S.C. Peacock, K. Maden and L. Kaplan:Pure Appl. Chem. 98, 107 (1981).
R.B. Davidson, N.K. Dalley, R.M. Izatt, J.J. Christensen, J.S. Bradshaw and C.F. Campana:Isr. J. Chem. 25, 27 (1985).
C.-Y. Zhu, R.M. Izatt, J.S. Bradshaw and N.K. Dalley:J. Incl. Phenom. 13, 17 (1992).
R.M. Izatt, C.-Y. Zhu, N.K. Dalley, J.C. Curtis, X. Kou and J.S. Bradshaw:J. Phys. Org. Chem. 5, 656 (1992).
R.B. Davidson, J.S. Bradshaw, B.A. Jones, N.K. Dalley, J.J. Christensen, R.M. Izatt, F.G. Morin and D.M. Grant:J. Org. Chem. 49, 353 (1984).
C.-Y. Zhu, J.S. Bradshaw, J.L. Oscarson and R.M. Izatt:J. Incl. Phenom. 12, 275 (1992).
J.K.M. Sanders and B.K. Hunter:Modern NMR Spectroscopy, Oxford University Press, Oxford (1987).
Atta-ur Rahman:Nuclear Magnetic Resonance, Springer-Verlag, New York (1986) pp. 126–130.
S.L. Baxter and J.S. Bradshaw:J. Heterocycl. Chem. 18, 233 (1981).
F.A. Bovey:Nuclear Magnetic Resonance Spectroscopy, 2nd Ed., Academic Press Inc., San Francisco (1988) p. 261.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Wang, T., Bradshaw, J.S., Curtis, J.C. et al. A structural analysis of the complexes of (S, S)-dimethylpyridino-18-crown-6 with (R) and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate by NMR techniques and molecular modeling. J Incl Phenom Macrocycl Chem 16, 113–122 (1993). https://doi.org/10.1007/BF00709146
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00709146