Chiral discrimination in diastereomeric salts of chlorine-substituted mandelic acid and phenylethylamine

Quan He; Hassan Gomaa; Sohrab Rohani; Jesse Zhu; Michael Jennings

doi:10.1002/chir.20822

Chiral discrimination in diastereomeric salts of chlorine-substituted mandelic acid and phenylethylamine

Quan He, Hassan Gomaa, Sohrab Rohani, Jesse Zhu, Michael Jennings

Research output: Journal Publication › Article › peer-review

17 Citations (Scopus)

Abstract

The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine were determined and are presented herein. The structure comparison between less soluble salts and more soluble salts shows that weak interactions such as CH/π interactions and van der Waals gain importance and contribute to chiral recognition when the hydrogen bonding patterns are very similar.

Original language	English
Pages (from-to)	707-716
Number of pages	10
Journal	Chirality
Volume	22
Issue number	8
DOIs	https://doi.org/10.1002/chir.20822
Publication status	Published - Aug 2010
Externally published	Yes

Keywords

Chiral recognition
Crystal structure
Diastereomeric salt
Hydrogen bonding
X-ray crystallographic analysis

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.20822

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abstract = "The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine were determined and are presented herein. The structure comparison between less soluble salts and more soluble salts shows that weak interactions such as CH/π interactions and van der Waals gain importance and contribute to chiral recognition when the hydrogen bonding patterns are very similar.",

keywords = "Chiral recognition, Crystal structure, Diastereomeric salt, Hydrogen bonding, X-ray crystallographic analysis",

author = "Quan He and Hassan Gomaa and Sohrab Rohani and Jesse Zhu and Michael Jennings",

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AU - He, Quan

AU - Gomaa, Hassan

AU - Rohani, Sohrab

AU - Zhu, Jesse

AU - Jennings, Michael

PY - 2010/8

Y1 - 2010/8

N2 - The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine were determined and are presented herein. The structure comparison between less soluble salts and more soluble salts shows that weak interactions such as CH/π interactions and van der Waals gain importance and contribute to chiral recognition when the hydrogen bonding patterns are very similar.

AB - The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine were determined and are presented herein. The structure comparison between less soluble salts and more soluble salts shows that weak interactions such as CH/π interactions and van der Waals gain importance and contribute to chiral recognition when the hydrogen bonding patterns are very similar.

KW - Chiral recognition

KW - Crystal structure

KW - Diastereomeric salt

KW - Hydrogen bonding

KW - X-ray crystallographic analysis

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U2 - 10.1002/chir.20822

DO - 10.1002/chir.20822

M3 - Article

C2 - 20143411

AN - SCOPUS:77955132030

SN - 0899-0042

VL - 22

SP - 707

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JO - Chirality

JF - Chirality

IS - 8

ER -

Chiral discrimination in diastereomeric salts of chlorine-substituted mandelic acid and phenylethylamine

Abstract

Keywords

ASJC Scopus subject areas

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