In situ synthesis of twelve dialkyltartrate-boric acid complexes and two polyols-boric acid complexes and their applications as chiral ion-pair selectors in nonaqueous capillary electrophoresis.
In this paper, twelve dialkyltartrate-boric acid complexes and two polyols-boric acid complexes were in situ synthesized by the reaction of different dialkyltartrates or polyols with boric acid in methanol containing triethylamine. All of the twelve dialkyltartrate-boric acid complexes were found to have relatively good chiral separation performance in nonaqueous capillary electrophoresis (NACE). Their chiral recognition effects in terms of both enantioselectivity (α) and resolution (R(s)) were similar when the number of carbon atoms was below six in the alkyl group of alcohol moiety. The dialkyltartrates containing alkyl groups of different structures but the same number of carbon atoms, i.e. one of straight chain and one of branched chain, also provided similar chiral recognition effects. Furthermore, it was demonstrated for the first time that two methanol insoluble polyols, D-mannitol and D-sorbitol, could react with boric acid to prepare chiral ion-pair selectors using methanol as the solvent medium.
National Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, Gansu, China.
Li-Juan
LJ
Wang
Juan
J
Yang
Geng-Liang
GL
Yang
Xing-Guo
XG
Chen
D000318:Adrenergic beta-Agonists / Q000302:isolation & purification; D000319:Adrenergic beta-Antagonists / Q000302:isolation & purification; D000438:Alcohols / Q000737:chemistry; D001888:Boric Acids / Q000138:chemical synthesis / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D013237:Stereoisomerism; D013644:Tartrates / Q000138:chemical synthesis / Q000737:chemistry*
D000318:Adrenergic beta-Agonists; D000319:Adrenergic beta-Antagonists; D000438:Alcohols; D001888:Boric Acids; D013644:Tartrates; C032688:boric acid; C029768:tartaric acid