化学
二氯甲烷
四氟硼酸盐
亚胺离子
三苯基膦
离子
氯仿
氯化物
离解(化学)
无机化学
红外光谱学
催化作用
药物化学
物理化学
有机化学
离子液体
溶剂
作者
Stephen H. Dempsey,Steven R. Kass
标识
DOI:10.1021/acs.joc.2c02001
摘要
A series of commonly used weakly coordinating cations (WCCs) including tetraalkylammonium, bis(triphenylphosphine)iminium (PPN), P2 and P5 phosphazenium, and tetraphenylphosphonium ions were investigated along with five additional tetraarylphosphonium ions [Ar = 4-Me, 4-t-Bu, 3,5-Me2, 4-Me2N, and 3,5-(MeO)2 phenyl derivatives]. Dissociation enthalpies of their chloride complexes were computed in the gas phase and in dichloromethane. These results are compared to infrared spectra of these salts in chloroform-d which provide free and bound C-D stretches, 19F NMR spectra of the corresponding tetrafluoroborate salts, ion-pair equilibrium constants, and reaction rates of the chlorides and acetates with 1-iodooctane. The latter transformation was also carried out under catalytic conditions. Substituted tetraphenylphosphonium ion derivatives are found to be surprisingly good WCCs that function as well or better than the P2 and P5 phosphazenium ions, the current WCC gold standard.
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