Demircioğlu Zeynep, Albayrak Çiğdem, Büyükgüngör Orhan
Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey.
Department of Chemistry, Faculty of Arts and Science, Sinop University, TR-57000 Sinop, Turkey.
Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jul 15;128:748-58. doi: 10.1016/j.saa.2014.02.186. Epub 2014 Mar 12.
A suitable single crystal of (E)-3-methoxy-2-[(p-tolylimino)methyl]phenol, formulated as C15H15N1O2, reveals that the structure is adopted to its E configuration about the azomethine C=N double bond. The compound adopts a enol-imine tautomeric form with a strong intramolecular O-H⋯N hydrogen bond. The single crystal X-ray diffraction analysis at 296K crystallizes in the monoclinic space group P21/c with a = 13.4791(11) Å, b = 6.8251(3) Å, c = 18.3561(15) Å, α = 90°, β = 129.296(5)°, γ = 90° and Z = 4. Comprehensive theoretical and experimental structural studies on the molecule have been carried out by FT-IR and UV-vis spectrometry. Optimized molecular structure and harmonic vibrational frequencies have been investigated by DFT/B3LYP method with 6-31G(d,p) basis set. Stability of the molecule, hyperconjugative interactions, charge delocalization and intramolecular hydrogen bond has been analyzed by using natural bond orbital (NBO) analysis. Electronic structures were discussed by TD-DFT method and the relocation of the electron density were determined. The energetic behavior of the title compound has been examined in solvent media using polarizable continuum model (PCM). Molecular electrostatic potential (MEP), Mulliken population method and natural population analysis (NPA) have been studied. Nonlinear optical (NLO) properties were also investigated. In addition, frontier molecular orbitals analysis have been performed from the optimized geometry. An ionization potential (I), electron affinity (A), electrophilicity index (ω), chemical potential (μ), electronegativity (χ), hardness (η), and softness (S), have been investigated.
一种化学式为C₁₅H₁₅NO₂的合适单晶（E）-3-甲氧基-2-[(对甲苯基亚氨基)甲基]苯酚表明，该结构围绕偶氮甲碱C=N双键采用E构型。该化合物采用烯醇-亚胺互变异构形式，具有强分子内O-H⋯N氢键。在296K下的单晶X射线衍射分析表明，其结晶于单斜空间群P21/c，a = 13.4791(11) Å，b = 6.8251(3) Å，c = 18.3561(15) Å，α = 90°，β = 129.296(5)°，γ = 90°，Z = 4。通过傅里叶变换红外光谱（FT-IR）和紫外可见光谱（UV-vis）对该分子进行了全面的理论和实验结构研究。采用DFT/B3LYP方法和6-31G(d,p)基组研究了优化后的分子结构和谐波振动频率。利用自然键轨道（NBO）分析对分子的稳定性、超共轭相互作用、电荷离域和分子内氢键进行了分析。通过TD-DFT方法讨论了电子结构并确定了电子密度的重新分布。使用极化连续介质模型（PCM）在溶剂介质中研究了标题化合物的能量行为。研究了分子静电势（MEP）、Mulliken布居方法和自然布居分析（NPA）。还研究了非线性光学（NLO）性质。此外，根据优化后的几何结构进行了前沿分子轨道分析。研究了电离势（I）、电子亲和势（A）、亲电指数（ω）、化学势（μ）、电负性（χ）、硬度（η）和软度（S）。
