Synthesis, experimental and theoretical studies on the factors influencing the pKa values of new crown ethers containing a diarylphosphinic acid unit

[摘要] Synthesis of acidic new crown ethers containing a diarylphosphinic acid unit has been accomplished. The aromatic rings of the crown ethers were substituted with tert-butyl and nitro groups. Nitro substitution of the crown ethers was investigated. pK(a) determination of the new proton-ionizable crown ethers has been performed, showing the effect of the substituents of the aromatic rings on the acidity. An anomaly was discovered in the pK(a) values and an explanation was given based on quantum mechanical calculations and molecular dynamics simulations. (C) 2016 Elsevier Ltd. All rights reserved.

[发布日期] 2016-12-29

[关键词] Proton-ionizable crown ethers;Diarylphosphinic acids;pK(a) determination;DFT, MD simulations;Acidity