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Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α ‐Phenylethyl Group
Author(s) -
CortésHernández Mayra,
RojasLima Susana,
HernándezRodríguez Marcos,
CruzBorbolla Julián,
LópezRuiz Heraclio
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500177
Subject(s) - chemistry , titration , urea , enantiomer , fluoride , allylic rearrangement , stereochemistry , proton nmr , chloride , group (periodic table) , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis
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 1 H‐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 (A 1,3 strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.