儿茶酚环扭转对羟黄酮的影响

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY Acta Chimica Slovaca Pub Date : 2020-04-01 DOI:10.2478/acs-2020-0008
M. Michalík, Monika Biela, D. Cagardová, Vladimír Lukes
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引用次数: 2

摘要

摘要对槲皮素和8种单羟基黄酮醇和生物羟基黄酮醇进行了系统的量子化学研究。基于密度泛函数理论的结构分析表明,在C5和C3原子上被羟基取代的黄酮醇的能量优先构象是通过(C4)O···HO(3或5)原子对之间形成的分子内氢键来稳定的。根据羟基位置的不同,苯基环相对于平面苯并-γ-吡咯酮部分的能量优选扭转取向在0 ~ 180度之间变化。利用时变DFT处理研究了气相电子跃迁。最大波长对苯环扭转变形的依赖性具有相似的形状,即在垂直方向上观察到最小,在平面方向上观察到最大。比较了最高已占分子轨道(HOMO)和最低未占分子轨道(LUMO)的形状和能量。得到的理论结果与已有的实验数据进行了比较。
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Influence of catecholic ring torsion on hydroxyflavones
Abstract Systematic quantum chemical investigation of quercetin and selected eight mono- and bihydroxyflavonols is presented. Structural analysis based on the Density Functional Theory showed that the energetically preferred conformation of flavonols substituted at the C5 and C3 atoms by a hydroxyl group is stabilised via intramolecular hydrogen bonds occurring between the (C4)O···HO(3 or 5) atomic pairs. Depending on the hydroxyl group positions, energetically preferred torsional orientation of the phenyl ring with respect to the planar benzo-γ-pyrone moiety changed from 0 to 180 degrees. Gas-phase electron transitions were investigated using the time-dependent DFT treatment. The dependence of maximal wavelengths on the torsional deformation of the phenyl ring is of a similar shape, i.e. minima observed for the perpendicular orientation and maxima for the planar one. Shape and energies of the Highest Occupied (HOMO) and Lowest Unoccupied (LUMO) Molecular Orbitals were compared. The obtained theoretical results were compared with available experimental data.
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来源期刊
Acta Chimica Slovaca
Acta Chimica Slovaca CHEMISTRY, MULTIDISCIPLINARY-
自引率
12.50%
发文量
11
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