Molecular recognition of biotin, barbital and tolbutamide with new synthetic receptors |
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Authors: | Rosa M. Claramunt,Fernando Herranz,Elena Pinilla,José Elguero |
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Affiliation: | a Departamento de Química Orgánica y Bio-Orgánica, UNED, Facultad de Ciencias, Senda del Rey 9, E-28040 Madrid, Spain b Laboratorio de Difracción de Rayos X, Departamento de Química Inorgánica, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain c Instituto de Química Médica, Centro de Química Orgánica ‘Manuel Lora-Tamayo’, C.S.I.C., Juan de la Cierva 3, E-28006 Madrid, Spain |
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Abstract: | We have measured, by means of NMR titrations, the binding constants for the complexes between hosts N,N′-bis(6-methylpyridin-2-yl)-1,3-benzenedicarboxamide (7) and 4-chloro-N,N′-bis(6-methylpyridin-2-yl)-2,6-pyridinedicarboxamide (8, hydrated) with biotin methyl ester (1), N,N′-dimethylurea (2), 2-imidazolidone (3), N,N′-trimethylenurea (4), barbital (5) and tolbutamide (6) as guests. Molecular Mechanics calculations (Monte Carlo Conformational Search, AMBER and OPLS force fields, MacroModel v.8.1) on the complexes formed between the foregoing guests and hosts 7 and 8, comparatively with 4-oxo-N,N′-bis(6-methylpyridin-2-yl)-1,4-dihydro-2,6-pyridinedicarboxamide (9a) have been carried out in order to determine the correlation between experimental and theoretical results and to understand the behaviour of the designed new hosts. Finally we have performed single point DFT [B3LYP/6-31G(d,p)] calculations on the optimised Molecular Mechanics geometries for the complexes between hosts 7-9 and water. |
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Keywords: | Molecular recognition Binding constants Molecular modelling NMR titrations |
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