title: Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition.
abstract: Two new diastereomeric chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral tethering group and a Π-basic chiral unit such as (R)-1-(1-naphthyl)ethylamine (CSP 1) or (S)-1-(1-naphthyl)ethylamine (CSP 2) were prepared. The two CSPs were applied to the enantiomeric separation of N-(3,5-dinitrobenzoyl)-1-phenylalkylamines and N-(3,5-dinitrobenzoyl)-α-amino acid derivatives using 20% isopropyl alcohol in hexane as a normal mobile phase. To elucidate the effect of the two chiral units on the chiral recognition, the chiral recognition abilities of the two CSPs were compared with each other and with that of a CSP (CSP 3) based on (R)-1-(1-naphthyl)ethylamine. From the chromatographic chiral recognition results, (R)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 1 were concluded to show a cooperative ("matched") effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative ("mismatched") effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. agneeswarichem@gmail.com.
authors.forename: Rajalingam
authors.initials: R
authors.lastname: Agneeswari
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. jysung@kbsi.re.kr.
authors.forename: Ji Yeong
authors.initials: JY
authors.lastname: Sung
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. dmsthf4834@hanmail.net.
authors.forename: Eun Sol
authors.initials: ES
authors.lastname: Jo
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. heeyoung0906@naver.com.
authors.forename: Hee Young
authors.initials: HY
authors.lastname: Jeon
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. tamilavan4811@gmail.com.
authors.forename: Vellaiappillai
authors.initials: V
authors.lastname: Tamilavan
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Pusan 609-735, Korea. mhhyun@pusan.ac.kr.
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D002851:Chromatography, High Pressure Liquid; D043844:Crown Ethers / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D043844:Crown Ethers; D005021:Ethylamines; D009281:Naphthalenes; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; C055450:1-(1-naphthyl)ethylamine
keywords: chiral stationary phase; chiral tethering group; enantiomer separation; liquid chromatography