Crystal Structure of 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic Acid and Synthesis, Spectroscopy, and DFT Study of Its Dibutyltin(IV) Complex

IF 0.4 4区 化学 Q4 CRYSTALLOGRAPHY Journal of Chemical Crystallography Pub Date : 2023-11-23 DOI:10.1007/s10870-023-00996-y
Pratima Debnath, Chinmoy Majumder, Arnab Bhattacharya, Paresh Debnath, Subhadip Roy, Alexander S. Novikov, Manojit Roy, Tarun Kumar Misra
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Abstract

The structure of the 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic acid (H3L) was confirmed by single crystal X-ray diffraction and Hirshfeld surface analysis was used further to quantify the intermolecular interactions. It crystallized in monoclinic space group P21/c. The observed bond distances evidence that the structure exists predominately in azo-enamine tautomeric form in the solid state. A novel dibutyltin(IV) complex, [(Bu2SnHL)2] (1) was synthesized from H3L. The complex was then characterized by studying different techniques including elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) spectroscopy. In solution state, the molar mass of the compound was confirmed by Mass spectrometry. Spectroscopy study guides to predict the structure of the complex which is supposed to be a cyclic dimer [(Bu2SnHL)2] and Sn(IV) adopts a six-coordinated geometry. However, in solution Sn(IV) adopts four coordinated distorted tetrahedral geometry which was supported by 119Sn NMR spectroscopy (δSn(119), 126.34 ppm) and EI-MS results of the complex ion ([C28H32N3O4Sn]+,m/z 593.1). Further, the structures in solid and solution state were supported by developing their optimized structures and IR data from the DFT calculation.

Graphical Abstract

The crystal structure of the ligand is in azo-enamine tautomeric form and in accordance with DFT study, its dibutyltin(IV) complex is a cyclic dimer, (Bu2SnHL)2, which becomes monomer in solution.

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2-((E)-(Z)-3-((4-羟基苯基)氨基)亚甲基)-4-氧环己基-1,5-二烯-1-基)二氮基)苯甲酸的晶体结构及其二丁基锡配合物的合成、光谱和DFT研究
用单晶x射线衍射证实了2-((E)-(Z)-3-((4-羟基苯基)氨基)亚甲基-4-氧环己基-1,5-二烯-1-基)二氮基)苯甲酸(H3L)的结构,并用Hirshfeld表面分析进一步定量了分子间相互作用。在单斜空间群P21/c中结晶。观察到的键距证明该结构在固体状态下主要以偶氮-烯胺互变异构形式存在。以H3L为原料合成了新型二丁基锡(IV)配合物[(Bu2SnHL)2](1)。然后通过元素分析、FT-IR和核磁共振(1H、13C和119Sn)光谱等不同技术对该配合物进行了表征。在溶液状态下,用质谱法测定了化合物的摩尔质量。光谱学研究指导预测了配合物的结构,该配合物假定为环状二聚体[(Bu2SnHL)2], Sn(IV)采用六坐标几何结构。而在溶液中,Sn(IV)呈四配位畸变四面体结构,这得到了119Sn核磁共振波谱(δSn(119), 126.34 ppm)和配合离子([C28H32N3O4Sn]+,m/z 593.1)的e - ms结果的支持。此外,通过优化结构和DFT计算得到的红外数据对固溶态结构进行了支持。配体的晶体结构为偶氮-烯胺互变异构形式,根据DFT研究,其二丁基锡(IV)配合物为环状二聚体(Bu2SnHL)2,在溶液中成为单体。
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来源期刊
CiteScore
1.50
自引率
12.50%
发文量
56
审稿时长
6.3 months
期刊介绍: Journal of Chemical Crystallography is an international and interdisciplinary publication dedicated to the rapid dissemination of research results in the general areas of crystallography and spectroscopy. Timely research reports detail topics in crystal chemistry and physics and their relation to problems of molecular structure; structural studies of solids, liquids, gases, and solutions involving spectroscopic, spectrometric, X-ray, and electron and neutron diffraction; and theoretical studies.
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