Synthesis, Spectroscopic, Crystal Structure, Hirshfeld Surface Analysis and DFT Calculations of (E)-N-(2,6-dichlorophenyl)-1-(5-nitro-2-(piperidin-1-yl)phenyl) Methanamine

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-09-04 DOI:10.1134/S0022476624080092

H. Özşanlı, S. N. Aygün, U. Çoruh, E. Ağar

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Abstract

In this study, experimental methods X-ray single crystal analysis, UV-Vis spectroscopy and FTIR spectroscopy, and theoretical method Density Functional Theory (DFT) were used to study the structure of the new Schiff base (E)-N-(2,6-dichlorophenyl)-1-(5-nitro-2-(piperidin-1-yl)phenyl) methanamine. Theoretical calculations of the title compound and FTIR harmonic vibration frequencies were carried out using B3LYP methods with the 6-31G(d,p) basis set. The optical properties have been studied by DFT calculation and the experimental UV-Vis spectrum presents its contribution to the HOMO‒LUMO boundary. The molecular electrostatic potential map (MEP-ESP), analysis of frontier molecular orbitals (FMO), and determination of thermodynamic properties for the title compound were conducted using identical levels of theory. Besides, the structural state and crystal packing of the title compound were analyzed using molecular structure, Hirshfeld surfaces, interactions energies, energy frameworks and electrophilicity-based charge transfer (ECT) with DNA bases.

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(E)-N-(2,6-二氯苯基)-1-(5-硝基-2-(哌啶-1-基)苯基)甲胺的合成、光谱、晶体结构、Hirshfeld 表面分析和 DFT 计算

摘要本研究采用 X 射线单晶分析、紫外可见光谱和傅立叶变换红外光谱等实验方法和密度泛函理论（DFT）等理论方法研究了新的席夫碱 (E)-N-(2,6-dichlorophenyl)-1-(5-nitro-2-(piperidin-1-yl)phenyl) methanamine 的结构。采用 6-31G(d,p) 基集的 B3LYP 方法对标题化合物和傅立叶变换红外谐振频率进行了理论计算。通过 DFT 计算研究了其光学性质，实验紫外可见光谱显示了其对 HOMO-LUMO 边界的贡献。利用相同的理论水平对标题化合物进行了分子静电位图（MEP-ESP）、前沿分子轨道（FMO）分析和热力学性质测定。此外，还利用分子结构、Hirshfeld 表面、相互作用能、能量框架以及与 DNA 碱基的亲电电荷转移（ECT）分析了标题化合物的结构状态和晶体堆积。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.