title: Novel C2-symmetric macrocycles bearing diamide-diester groups: synthesis and enantiomeric recognition for primary alkyl ammonium salts.
abstract: We synthesized a series of novel macrocycles with diamide-diester groups (S,S)-1, (S,S)-2, (S,S)-3, and (R,R)-1, derived from dimethyloxalate and amino alcohols by high dilution technique, and evaluated enantiomeric recognition properties of these macrocycles toward primary alkyl ammonium salts by 1H NMR titration. Taking into account the host employed, important differences were observed in the Ka values of (R)-Am and (S)-Am for (S,S)-1 and (R,R)-1 hosts, KS/KR = 5.55 and KR/KS = 3.65, Delta Delta Go = 0.43 and -0.32 kJ mol-1, respectively. There seems a general tendency for the host to include the guests with the same absolute configuration.
authors.affiliation: Chemistry Department, University of Dicle, Faculty of Art and Science, 21280-Diyarbakir, Turkey.
authors.forename: Murat
authors.initials: M
authors.lastname: Sunkur
authors.forename: Deniz
authors.initials: D
authors.lastname: Baris
authors.forename: Halil
authors.initials: H
authors.lastname: Hosgoren
authors.forename: Mahmut
authors.initials: M
authors.lastname: Togrul
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry; D003958:Diamide / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D004952:Esters; D047028:Macrocyclic Compounds; D000644:Quaternary Ammonium Compounds; D003958:Diamide