Effect of a substituent on an aromatic group in diastereomeric resolution

Kazushi Kinbara; Koji Oishi; Yoshiko Harada; Kazuhiko Saigo

doi:10.1016/S0040-4020(00)00472-5

Effect of a substituent on an aromatic group in diastereomeric resolution

Kazushi Kinbara, Koji Oishi, Yoshiko Harada, Kazuhiko Saigo

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6651-6655
Number of pages	5
Journal	Tetrahedron
Volume	56
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4020(00)00472-5
Publication status	Published - 2000
Externally published	Yes

Keywords

Chiral discrimination
Crystal engineering
Diastereomer method

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00472-5

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title = "Effect of a substituent on an aromatic group in diastereomeric resolution",

abstract = "The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.",

keywords = "Chiral discrimination, Crystal engineering, Diastereomer method",

author = "Kazushi Kinbara and Koji Oishi and Yoshiko Harada and Kazuhiko Saigo",

note = "Funding Information: The present work was supported by Grants-in-Aid for Scientific Research (Nos. 09450330 and 10750618) from the Ministry of Education, Science, Sports and Culture of Japan, and the Kawakami Memorial Foundation.",

year = "2000",

doi = "10.1016/S0040-4020(00)00472-5",

language = "English",

volume = "56",

pages = "6651--6655",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "36",

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TY - JOUR

T1 - Effect of a substituent on an aromatic group in diastereomeric resolution

AU - Kinbara, Kazushi

AU - Oishi, Koji

AU - Harada, Yoshiko

AU - Saigo, Kazuhiko

N1 - Funding Information: The present work was supported by Grants-in-Aid for Scientific Research (Nos. 09450330 and 10750618) from the Ministry of Education, Science, Sports and Culture of Japan, and the Kawakami Memorial Foundation.

PY - 2000

Y1 - 2000

N2 - The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

AB - The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.

KW - Chiral discrimination

KW - Crystal engineering

KW - Diastereomer method

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U2 - 10.1016/S0040-4020(00)00472-5

DO - 10.1016/S0040-4020(00)00472-5

M3 - Article

AN - SCOPUS:0033812931

VL - 56

SP - 6651

EP - 6655

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 36

ER -

Effect of a substituent on an aromatic group in diastereomeric resolution

Abstract

Keywords

ASJC Scopus subject areas

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