Chemistry - A European Journal p. 8136 - 8143 (2013)
Update date:2022-08-04
Topics: Synthesis Chiral Properties Structure Application Zwitterionic
Sheshenev, Andrey E.
Boltukhina, Ekaterina V.
Grishina, Anastasiya A.
Cisa?ova, Ivana
Lyapkalo, Ilya M.
Hii, King Kuok
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. A convenient synthetic approach to a new class of chiral zwitterionic phosphorus-containing heterocycles starting from methylene-bridged bis(imidazolines) was designed and executed. Stability and properties of the synthesized compounds were investigated. The applicability of the designed compounds as chiral solvating agents for the determination of the enantiomeric excesses of chiral acids was demonstrated. Copyright
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