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Crystals 2017, 7(9), 263; doi:10.3390/cryst7090263

Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines

1
Institute of Agrobiological Sciences, National Agriculture and Food Research Organization (NARO), Tsukuba 305-8634, Japan
2
Advanced Analysis Center, National Agriculture and Food Research Organization (NARO), Tsukuba 305-8642, Japan
3
Department of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women’s University, Nara 630-8506, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Dmitriy V Soldatov
Received: 26 July 2017 / Revised: 15 August 2017 / Accepted: 22 August 2017 / Published: 28 August 2017
(This article belongs to the Special Issue Crystal Structure Analysis of Supramolecular and Porous Solids)
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Abstract

The crystal structures of salts 69 prepared from (R)-2-methoxy-2-(1-naphthyl)propanoic acid [(R)-MαNP acid, (R)-1] and (R)-1-arylethylamines [salt 6, (R)-1-(4-methoxyphenyl)ethylamine∙(R)-1; salt 7, (R)-1-(4-fluorophenyl)ethylamine∙(R)-1; salt 8, (R)-1-(4-chlorophenyl)ethylamine∙(R)-1; and salt 9, (R)-1-(3-chlorophenyl)ethylamine∙(R)-1] were elucidated by X-ray crystallography. The solid-state associations and conformations of the MαNP salts were defined using the concepts of supramolecular- and planar chirality, respectively, and the crystal structures of salts 69 were interpreted as a three-step hierarchical assembly. The para-substituents of the (R)-1-arylethylammonium cations were found on sheet structures consisting of 21 columns. Thus, salts possessing smaller para-substituents, that is, salt 7 (p-F) and salt 9 (p-H), and larger para-substituents, that is, salt 6 (p-OMe) and salt 8 (p-Cl), crystallized in the space groups P21 and C2, respectively. Additionally, weak intermolecular interactions, that is, aromatic C–H···π, C–H···F, and C–H···O interactions, were examined in crystalline salts 69. View Full-Text
Keywords: chiral recognition; crystal engineering; planar chirality; supramolecular chirality chiral recognition; crystal engineering; planar chirality; supramolecular chirality
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Ichikawa, A.; Ono, H.; Mikata, Y. Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines. Crystals 2017, 7, 263.

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