Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo

研究成果: Article査読

36 被引用数 (Scopus)

抄録

Enantiopure cis-1-aminoindan-2-ol was selected as a basic resolving agent for racemic 2-arylalkanoic acids on the basis that its rigid cis-conformation would favor the formation of a supramolecular hydrogen-bonded column, in which chiral discrimination of the racemic carboxylate would occur. It was found that this amino alcohol possesses high resolving efficiency for a variety of racemic acids; also, X-ray crystallographic analyses of the diastereomeric salts showed that a columnar hydrogen-bond network is formed in both the less- and more-soluble diastereomeric salts, as we had expected. A detailed study on the stabilising interactions suggested that there are two that play an important role: (i) hydrogen bonding between the ammonium and hydroxy groups and the acid carboxylate, which determines the formation of the columnar network and (ii) CH...π, which influences the herringbone packing of the aromatic groups, implying that it also plays some role in chiral discrimination.

本文言語English
ページ(範囲)111-119
ページ数9
ジャーナルJournal of the Chemical Society. Perkin Transactions 2
1
出版ステータスPublished - 2000 1月 1

ASJC Scopus subject areas

  • 化学 (全般)

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