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2004•Organic LettersRequires access

A New Hydrogen-Bonding Motif for Chiral Recognition in the Diastereomeric Salts of Racemic 1-Phenylethylamine Derivatives with Enantiopure O-Ethyl Phenylphosphonothioic Acid

Yuka Kobayashi, F. Morisawa, Kazuhiko Saigo

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Abstract

An enantiopure phosphonothioic acid showed a unique and superior chiral recognition ability, arising from its P-stereogenicity, for racemic 1-phenylethylamine derivatives through diastereomeric crystallization. Spherical molecular clusters, associated by hydrogen bonds and CH/pi interactions, aggregated with high symmetry in the less-soluble diastereomeric salts.

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What this paper is about

An enantiopure phosphonothioic acid showed a unique and superior chiral recognition ability, arising from its P-stereogenicity, for racemic 1-phenylethylamine derivatives through diastereomeric crystallization. Spherical molecular clusters, associated by hydrogen bonds and CH/pi interactions, aggregated with high symmetry in the less-soluble diastereomeric salts.

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Available abstract

An enantiopure phosphonothioic acid showed a unique and superior chiral recognition ability, arising from its P-stereogenicity, for racemic 1-phenylethylamine derivatives through diastereomeric crystallization. Spherical molecular clusters, associated by hydrogen bonds and CH/pi interactions, aggregated with high symmetry in the less-soluble diastereomeric salts.

Key concepts: Enantiopure drug, Diastereomer, Chemistry, Hydrogen bond, Crystallization, Stereochemistry, Organic chemistry, Molecule

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A New Hydrogen-Bonding Motif for Chiral Recognition in the Diastereomeric Salts of Racemic 1-Phenylethylamine Derivatives with Enantiopure O-Ethyl Phenylphosphonothioic Acid — Research Paper | ScholarLens