Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra

Takahiro Furo, Tadashi Mori, Yumi Origane, Takehiko Wada, Hiroshi Izumi, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory CDFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4SP;12SP)-1 and (4Sp;12Rp)-2, respectively.

Original languageEnglish
Pages (from-to)205-211
Number of pages7
JournalChirality
Volume18
Issue number3
DOIs
Publication statusPublished - 2006 Mar 10
Externally publishedYes

Keywords

  • Charge-transfer interaction
  • Chiral cyclophane
  • DFT calculation
  • Exciton coupling method
  • Vibrational circular dichroism spectroscopy

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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