Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, Lodz90-236, Poland.
Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, Lodz91-403, Poland.
J Org Chem. 2023 Feb 17;88(4):2132-2139. doi: 10.1021/acs.joc.2c02547. Epub 2023 Feb 3.
The present study investigates the effect of the substitution of salicylaldehyde hydrazones at two selected positions, i.e., the -position with regard to the proton-donating and proton-accepting centers forming the hydrogen bridge. A detailed analysis of structural data obtained by theoretical approaches and X-ray experiments, together with original resonance Hammett's constants, indicates that the strength of the intramolecular hydrogen bonding present in salicylaldehyde hydrazones can be selectively modulated by substitution of the parent molecular system with the chemical group of known π-electron-donating or -accepting properties. Our findings provide an insight into planning synthesis pathways for salicylaldehyde hydrazone species and predicting their result with regard to their H-bonding and related physical and chemical properties.
本研究考察了水杨醛腙在两个选定位置取代的效果，即质子供体和质子受体中心形成氢键的 - 位。通过理论方法和 X 射线实验获得的结构数据的详细分析，以及原始的共振哈米特常数，表明水杨醛腙中存在的分子内氢键的强度可以通过用具有已知π-供电子或吸电子性质的化学基团取代母体分子系统来选择性调节。我们的研究结果为水杨醛腙物种的合成途径规划提供了深入了解，并预测了它们的氢键及其相关物理和化学性质的结果。
