Enantioselective recognition of ammonium perchlorate salts by optically active monoaza-15-crown-5 ethers.
Chiral monoaza-15-crown-5 ethers (1, 2) were prepared from (R)-(-)-2-amino-1-butanol in high yield. The chiral monoaza-15-crown-5 ethers were purified directly as NaClO(4) complexes. Molecular recognition by these chiral monoaza-crown ethers of (R)- and (S)-PhEtHClO(4) and (R)- and (S)-NapEtHClO(4) as characterized by UV-vis spectroscopy. The order of enantiomeric selectivity is (R)- > (S)- PhEtHClO(4) and (S)- > (R)-NapEtHClO(4) for 1. In the case of 2 it was (R)- > (S)-PhEtHClO(4) and (R)- > (S)- NapEtHClO(4). The cavity of macrocycle and steric hindrance of the benzene units appears to play an important role in recognition.
Togrul
Mahmut
M
Department of Chemistry, Faculty of Science, University of Dicle, Diyarbakir, Turkey. mtogrul@dicle.ed.tr
Turgut
Yilmaz
Y
Hoşgören
Halil
H
D000042:Absorption; D000596:Amino Acids / Q000737:chemistry*; D001692:Biological Transport; D002621:Chemistry / Q000379:methods*; D004987:Ethers / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D010472:Perchlorates / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013053:Spectrophotometry; D013237:Stereoisomerism; D013816:Thermodynamics; D014466:Ultraviolet Rays
D000596:Amino Acids; D004987:Ethers; D010472:Perchlorates; D000644:Quaternary Ammonium Compounds; C053506:ammonium perchlorate