The chiral monoaza-15-crown-5 ethers 4 and 5 were prepared from L-phenylalaninol and L-leucinol, respectively. The molecular recognition of these chiral crown ethers for L-amino acid ethyl esters was characterised by UV-visible spectroscopy. Binding constants (Ka), free-energy changes (–ΔGo), enthalpy changes (ΔH) and entropy change (ΔS) values were determined for hosts 4 and 5 with L-amino acid ethyl ester hydrochlorides in CHCl3.
IzattR.M., ZhuC. Y., HuszthyP., and BradshawJ. S., in Crown Ethers: Toward Future Applications; CooperS.R., Ed.; VCH, New York, 1993.
2.
PedersenC.J., in Synthetic Multidentate Macrocyclic Compounds, IzattR.M., and ChristensenJ. J., eds. Academic Press, New York, 1978, p. 21.
3.
LambJ.D., IzattR. M., ChristensenJ. J., and EatoughD. J., in Coordination Chemistry of Macrocyclic Compounds, MelsonG.A., Ed., Plenum Press, New York, 1979.
4.
StoddartJ.F., in The Chemistry of Enzyme Action, PageM.E., Ed., Elsevier Science Publishers, Amsterdam, 1984.