Karakaplan, MehmetAk, DevranColak, MehmetKocakaya, Safak OzhanHosgoren, HalilPirinccioglu, Necmettin2024-04-242024-04-2420130040-40201464-5416https://doi.org/10.1016/j.tet.2012.10.020https://hdl.handle.net/11468/16088The synthesis of four diaza-18-crown-6 ethers with C-2-symmetry derived from trans-(R,R)-1,2-diaminocyclohexane bearing methyl, phenyl and phenoxymethyl moeities attached to a stereogenic centre on the crown ring were achieved. Enantiomeric discrimination of these macrocycles against amino acid methyl ester salts was examined by H-1 NMR titration method. They exhibit strong binding ability and some of them show a very high enantioselectivity towards amino acid esters, corresponding to 537 kJ/mol of binding energy difference in CDCl3 at 25 degrees C. Computational modelling showed parallel results with experimental calculations, thus providing a detailed understanding of molecular recognition mode and binding sites between the hosts and the guests. (C) 2012 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessChiral Amino AlcoholsChiral Diaza Crown EthersEnantiomeric RecognitionAmino Acid EstersH-1 Nmr TitrationComputational ModellingArticle691349358WOS:0003133861000452-s2.0-8487006663810.1016/j.tet.2012.10.020Q3Q2