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Absolute Configuration Determination of a New Chiral Rigid Bisetherketone Macrocycle Containing Binaphthyl and Thioether Moieties by Vibrational Circular Dichroism
Author(s) -
Cao Hui,
Ben Teng,
Su Zhongmin,
Zhang Min,
Kan Yuhe,
Yan Xue,
Zhang Wanjin,
Wei Yen
Publication year - 2005
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200400486
Subject(s) - absolute configuration , thioether , vibrational circular dichroism , chemistry , circular dichroism , molecule , infrared spectroscopy , crystallography , infrared , density functional theory , stereochemistry , computational chemistry , organic chemistry , physics , optics
Summary: A new chiral rigid bisetherketone macrocycle containing binaphthyl and thioether moieties was synthesized successfully using a modified pseudo‐high dilution technique. The compound was characterized by means of infrared absorption (IR) and vibrational circular dichroism (VCD). The experimental IR and VCD spectra were compared with those computed based on density functional theory (DFT) calculations at B3LYP/6‐31G (d) level. Good agreement was observed between the experimental and calculated spectra and, therefore, the absolute configuration was determined. Knowledge of the absolute configuration is of great importance when exploring the mechanisms of chiral recognition based on the chiral macrocyclic molecules.Structure of the new chiral rigid bisetherketone macrocycle produced.