Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

Fumio Toda; Koichi Tanaka; Zafra Stein; Israel Goldberg

doi:10.1021/jo00098a038

Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

Fumio Toda^*, Koichi Tanaka, Zafra Stein, Israel Goldberg

^*Corresponding author for this work

School of Chemistry

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112 Scopus citations

Abstract

Racemic 2,2′-dihydroxy-1,1′-binaphthyl and 10,10′-dihydroxy-9,9′-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides. The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes. The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.

Original language	English
Pages (from-to)	5748-5751
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	59
Issue number	19
DOIs	https://doi.org/10.1021/jo00098a038
State	Published - 1 Sep 1994

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title = "Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials",

abstract = "Racemic 2,2′-dihydroxy-1,1′-binaphthyl and 10,10′-dihydroxy-9,9′-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides. The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes. The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.",

author = "Fumio Toda and Koichi Tanaka and Zafra Stein and Israel Goldberg",

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Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials. / Toda, Fumio; Tanaka, Koichi; Stein, Zafra et al.
In: Journal of Organic Chemistry, Vol. 59, No. 19, 01.09.1994, p. 5748-5751.

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

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T1 - Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

AU - Toda, Fumio

AU - Tanaka, Koichi

AU - Stein, Zafra

AU - Goldberg, Israel

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N2 - Racemic 2,2′-dihydroxy-1,1′-binaphthyl and 10,10′-dihydroxy-9,9′-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides. The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes. The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.

AB - Racemic 2,2′-dihydroxy-1,1′-binaphthyl and 10,10′-dihydroxy-9,9′-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides. The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes. The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.

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Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

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