Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α‐Phenylethyl Group |
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| Authors: | Mayra Cortés‐Hernández Susana Rojas‐Lima Marcos Hernández‐Rodríguez Julián Cruz‐Borbolla Heraclio López‐Ruiz |
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| Institution: | 1. área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, México;2. Instituto de Química, Universidad Nacional Autónoma de México, México D.F, México |
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| Abstract: | An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by 1H‐NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6‐311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3‐strain (A1,3 strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers. |
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| Keywords: | Ab initio calculations Density functional theory Hydrogen bonds Binding constant |
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