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 journalArticlepeer-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 languageEnglish
Pages (from-to)1411-1413
Number of pages3
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume69
Issue number11
DOIs
Publication statusPublished - 2013 Nov
Externally publishedYes

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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