New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

作者:Sheshenev Andrey E; Boltukhina Ekaterina V; Grishina Anastasiya A; Cisarova Ivana; Lyapkalo Ilya M; Hii King Kuok*
来源:Chemistry - A European Journal, 2013, 19(25): 8136-8143.
DOI:10.1002/chem.201300062

摘要

A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods.

  • 出版日期2013-6