Journal of Organic Chemistry 2011-08-19

Synthetic hosts for molecular recognition of ureas.

Dolores Santa María, M Ángeles Farrán, M Ángeles García, Elena Pinilla, M Rosario Torres, José Elguero, Rosa M Claramunt

Index: J. Org. Chem. 76(16) , 6780-8, (2011)

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Abstract

Four hosts (7-10) containing 2,6-bisamidopyridine- and 2,5-bisamidopyrrole-bearing pyridyl or 1,8-naphthyridyl groups have been prepared and their structures studied by a combination of multinuclear NMR spectroscopy and X-ray crystallography. Their behavior in molecular recognition of urea derivatives, including (+)-biotin methyl ester, has been approached by molecular modeling (Monte Carlo conformational search, AMBER force field). The minimum energy values for the complexes are correlated with the experimental binding energies determined by means of (1)H NMR titrations.