Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.
Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.
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DOI：
10.1021/jo200950s
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发表时间：
2011-10-07
影响因子：
3.6
通讯作者：
Woerpel, K. A.
中科院分区：
文献类型：
--
作者：
Dibble, David J.;Ziller, Joseph W.;Woerpel, K. A.
在溶液中，几种4-取代环己酮肼盐的轴向构象占主导地位。分子电荷和溶剂极性的变化导致了每个分子构象择优的变化，这与轴向构象的静电稳定是一致的。通过与构象受限的反式十酮类化合物和计算模型的比较，用~1H核磁共振波谱分析确定了环己酮类底物的结构。X-射线单晶分析表明，在固态条件下，苯氧基的轴向构型是亚胺离子的择优构象。中性肼的结构也被确定为有利于固体中侧基苯氧基的轴向构型。
The axial conformer of several 4-substituted cyclohexanone hydrazone salts was found to predominate in solution. Changes in the charge of the molecule and the polarity of the solvent led to changes in the conformational preference of each molecule that was consistent with electrostatic stabilization of the axial conformer. 1H NMR spectroscopic analysis was utilized to determine the structure of cyclohexanone-derived substrates by comparison to conformationally restricted trans-decalone derivatives and computational models. X-ray crystallography demonstrated that the axial configuration of a pendant benzyloxy group is the preferred conformation of an iminium ion in the solid state. The structure of a neutral hydrazone was also determined to favor the axial configuration for a pendant benzyloxy group in the solid state.
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影响因子：
2.9
作者：
Anizelli, Pedro R.;Vilcachagua, Janaina D.;Tormena, Claudio F.
通讯作者：
Tormena, Claudio F.
影响因子：
2.9
作者：
Gauze, Gisele F.;Basso, Ernani A.;Tormena, Claudio F.
通讯作者：
Tormena, Claudio F.
影响因子：
3.6
作者：
Dudley, TJ;Smoliakova, IP;Hoffmann, MR
通讯作者：
Hoffmann, MR
影响因子：
1.8
作者：
ABDELMAGID, AF;MARYANOFF, CA;CARSON, KG
通讯作者：
CARSON, KG
影响因子：
15
作者：
CREMER, D;POPLE, JA
通讯作者：
POPLE, JA