Equilibrium NH acidities of acridan, phenanthridone, 9-acridone, and substituted 9-acridones
Equilibrium NH acidities of acridan, phenanthridone, 9-acridone, and substituted 9-acridones
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吖啶酮、菲啶酮、9-吖啶酮和取代的 9-吖啶酮的平衡 NH 酸度
DOI：
10.1007/bf00513441
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发表时间：
1982
影响因子：
1.5
通讯作者：
A. I. Shatenshteîn
中科院分区：
文献类型：
--
作者：
N. N. Voinovskaya;M. Terekhova;T. Sakhno;G. Val'kova;L. F. Rybakova;É. S. Petrov;A. I. Shatenshteîn
在二甲基亚砜(DMSO)中，用过渡金属化的方法测定了吖啶、菲、酮和2-取代的9-吖啶酮(取代基：Me2N、MeO、F、BrI和NO2)的平衡NH酸。讨论了杂环的共轭作用和芳香性在稳定阴离子中的作用。用CNDO/2(完全忽略微分重叠)方法计算了菲替酮和9-吖啶酮的去质子化能，计算结果与实验结果基本一致。2-取代9-吖啶酮类化合物的依赖pk=16.2−3.37σI−1.84σR(S 0.23，r 0.989)。
The equilibrium NH acidities of acridan, phenanthridone, 9-acridone, and 2-substituted 9-acridones (substituents: Me2N, MeO, F, Br, I, and NO2) were measured by transmetallation in dimethyl sulfoxide (DMSO). The role of conjugation and the aromatic character of the heterocyclic ring in stabilization of the anions is discussed. The energies of deprotonation of phenanthridone and 9-acridone were estimated by the CNDO/2 (complete neglect of differential overlap) method; it is shown that the difference between them is in agreement with the experimental results. The dependence pK = 16.2 − 3.37σI − 1.84σR (s 0.23, r 0.989) was obtained for the 2-substituted 9-acridones.