Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol

Yuko Kawanami; Hidekazu Tanaka; Jun Ichi Mizoguchi; Nobuko Kanehisa; Gaku Fukuhara; Masaki Nishijima; Tadashi Mori; Yoshihisa Inoue

doi:10.1107/S0108270113028461

Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol

Yuko Kawanami, Hidekazu Tanaka, Jun Ichi Mizoguchi, Nobuko Kanehisa, Gaku Fukuhara, Masaki Nishijima, Tadashi Mori, Yoshihisa Inoue

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

3 Citations (Scopus)

Abstract

The absolute configuration has been established of the enantiopure anti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with l-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl) pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11- bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C₅H₁₂NO⁺·C ₃₀H₁₉O₄ ^-·CH ₂Cl₂. In the crystal structure, the AC dimer interacts with l-prolinol through a nine-membered hydrogen-bonded ring [R 2 ²(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.

Original language	English
Pages (from-to)	1411-1413
Number of pages	3
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	69
Issue number	11
DOIs	https://doi.org/10.1107/S0108270113028461
Publication status	Published - 2013 Nov
Externally published	Yes

Keywords

L-prolinol
absolute configuration
anthracene-2-carboxylic acid
anti-headto-head cyclodimer
circular dichroism spectra
crystal structure

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)

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10.1107/S0108270113028461

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Kawanami, Y., Tanaka, H., Mizoguchi, J. I., Kanehisa, N., Fukuhara, G., Nishijima, M., Mori, T., & Inoue, Y. (2013). Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol. Acta Crystallographica Section C: Crystal Structure Communications, 69(11), 1411-1413. https://doi.org/10.1107/S0108270113028461

Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol. / Kawanami, Yuko; Tanaka, Hidekazu; Mizoguchi, Jun Ichi; Kanehisa, Nobuko; Fukuhara, Gaku; Nishijima, Masaki; Mori, Tadashi; Inoue, Yoshihisa.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 69, No. 11, 11.2013, p. 1411-1413.

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

Kawanami, Y, Tanaka, H, Mizoguchi, JI, Kanehisa, N, Fukuhara, G, Nishijima, M, Mori, T & Inoue, Y 2013, 'Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol', Acta Crystallographica Section C: Crystal Structure Communications, vol. 69, no. 11, pp. 1411-1413. https://doi.org/10.1107/S0108270113028461

Kawanami, Yuko ; Tanaka, Hidekazu ; Mizoguchi, Jun Ichi ; Kanehisa, Nobuko ; Fukuhara, Gaku ; Nishijima, Masaki ; Mori, Tadashi ; Inoue, Yoshihisa. / Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol. In: Acta Crystallographica Section C: Crystal Structure Communications. 2013 ; Vol. 69, No. 11. pp. 1411-1413.

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title = "Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol",

abstract = "The absolute configuration has been established of the enantiopure anti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with l-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl) pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11- bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C 30H19O4 -·CH 2Cl2. In the crystal structure, the AC dimer interacts with l-prolinol through a nine-membered hydrogen-bonded ring [R 2 2(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.",

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author = "Yuko Kawanami and Hidekazu Tanaka and Mizoguchi, {Jun Ichi} and Nobuko Kanehisa and Gaku Fukuhara and Masaki Nishijima and Tadashi Mori and Yoshihisa Inoue",

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AU - Fukuhara, Gaku

AU - Nishijima, Masaki

AU - Mori, Tadashi

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AB - The absolute configuration has been established of the enantiopure anti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with l-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl) pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11- bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C 30H19O4 -·CH 2Cl2. In the crystal structure, the AC dimer interacts with l-prolinol through a nine-membered hydrogen-bonded ring [R 2 2(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.

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Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with l-prolinol

Abstract

Keywords

ASJC Scopus subject areas

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