PROTON AFFINITIES AND THE SITE OF PROTONATION OF ENAMINES IN THE GAS-PHASE
PROTON AFFINITIES AND THE SITE OF PROTONATION OF ENAMINES IN THE GAS-PHASE
复制标题
DOI：
10.1021/ja00408a017
复制
发表时间：
1981-01-01
影响因子：
15
通讯作者：
FARNETH, WE
中科院分区：
文献类型：
--
作者：
ELLENBERGER, MR;DIXON, DA;FARNETH, WE
用离子回旋共振谱测量了一些甲基取代烯胺和亚胺的气相质子亲合能。的烯胺与相应的胺的质子亲和力的取代基的效果的比较是用来表明，在气相中的质子化发生在碳导致形成的亚胺离子。甲基取代的大的取代基效应的观察也表明，有一个显着量的离域的正电荷的亚胺离子。与溶液相的烯胺的碱度的比较。
The gas-phase proton affinities of a number of methyl-substituted enamines and imines havebeen measured using ion cyclotron resonance spectroscopy. Comparison of the effect of substituents on the proton affinities of the enamines with those of corresponding amines is used to show that protonation in the gas phase occurs at carbon leading to the formation of an iminium ion. The observation of a large substituent effect for substitution of an-methyl group also suggests that there is a significant amount of delocalization of positive charge in the iminium ion. A comparison with solution-phase basicities of enamines is also presented.