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Synthesis and p K a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies
Author(s) -
Németh Tamás,
Dargó Gergő,
Petró József Levente,
Petrik Zsófia,
Lévai Sándor,
Krámos Balázs,
Béni Zoltán,
Nagy József,
Balogh György Tibor,
Huszthy Péter,
Tóth Tünde
Publication year - 2017
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22721
Subject(s) - chemistry , enantiopure drug , enantiomer , crown ether , enantioselective synthesis , protonation , high performance liquid chromatography , covalent bond , organic chemistry , stereochemistry , medicinal chemistry , chromatography , catalysis , ion
New enantiopure dimethyl‐substituted acridino‐18‐crown‐6 and acridino‐21‐crown‐7 ethers containing a carboxyl group at position 9 of the acridine ring [( S,S )‐ 8 , ( S,S )‐ 9 , ( R,R )‐ 10 ] were synthesized. The p K a values of the new crown ethers [( S,S )‐ 8 , ( S,S )‐ 9 , ( R,R )‐ 10 ] and of an earlier reported macrocycle [( R,R )‐ 2 ] were determined by UV‐pH titrations. Crown ether ( S,S )‐ 8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [( S,S )‐CSP‐ 12 ] was studied by high‐performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1‐NEA. Ligands ( S,S )‐ 9 and ( R,R )‐ 10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.