二羧酸环亚胺新(三氟硅基)丙基衍生物的合成、实验和计算研究

IF 2.1 3区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR
Yu.I. Bolgova, T.N. Aksamentova, O.M. Trofimova, A.I. Albanov, A.I. Emel'yanov, M.A. Stepanov, T.N. Borodina, A.S. Pozdnyakov
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引用次数: 0

摘要

通过傅立叶变换红外光谱仪(FTIR)和结构分析法,合成了新的(三氟硅基)丙基环状二羧酸亚胺衍生物 1-[3-(三氟硅基)丙基]吡咯烷-2,5-二酮、1-[3-(三氟硅基)丙基]哌啶-2、6-二酮和 2-[3-(三氟硅基)丙基]-1H-异吲哚-1,3(2H)-二酮的合成,并通过傅立叶变换红外光谱、核磁共振光谱、质谱和元素分析对其结构进行了表征。分子内配位相互作用 O→Si 以及碳氢链长度对二羧酸环酰亚胺的 Si-氟乙基和 Si-氟丙基衍生物中配位相互作用强度的影响通过 DFT 计算进行了表征。还确定了所研究分子的几何、能量和电子特性。在(三氟硅烷基)乙基衍生物邻苯二甲酰亚胺的气相中观察到了分子内 O→Si 配位键,它关闭了六元螯合循环 SiCCN(C=O);在(三氟硅烷基)乙基衍生物琥珀酰亚胺的气相和二甲基亚砜溶液中都观察到了 O→Si 配位键。在气相中,(三氟硅基)丙基衍生物琥珀酰亚胺中发现了 O→Si 配位键,它关闭了七元螯合循环 SiCCCN(C=O)。量子化学计算是在 M06/6-311G** 和 MP2/6-311++G**//M06/6-311G** 水平上以 6-311G** 基集进行的。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis, experimental and computational studies of new (trifluorosilyl)propyl derivatives of cyclic imides of dicarboxylic acids

Synthesis, experimental and computational studies of new (trifluorosilyl)propyl derivatives of cyclic imides of dicarboxylic acids

New (trifluorosilyl)propyl derivatives of cyclic dicarboxylic acid imides 1-[3-(trifluorosilyl)propyl]pyrrolidine-2,5‑dione, 1-[3-(trifluorosilyl)propyl]piperidine-2,6‑dione and 2-[3-(trifluorosilyl)propyl]-1H-isoindole-1,3(2H)‑dione were synthesized and structurally characterized by FTIR, NMR spectroscopy, mass spectrometry and elemental analysis. Intramolecular coordination interaction O→Si and the influence of the hydrocarbon chain length on the strength of the coordination interaction in Si-fluoroethyl and Si-fluoropropyl derivatives of cyclic imides of dicarboxylic acids were characterized by DFT calculations. The geometric, energetic and electronic characteristics of the investigated molecules were also determined. The intramolecular O→Si coordination bond, closing the six-membered chelate cycle SiCCN(C=O), is observed in the (trifluorosilyl)ethyl derivative phthalimide in the gas, and in the (trifluorosilyl)ethyl derivative succinimide the O→Si coordination bond is observed both in the gas phase and in DMSO solution. The coordination bond O→Si, closing the seven-membered chelate cycle SiCCCN(C=O), is found in the (trifluorosilyl)propyl derivative succinimide in the gas phase. Quantum chemical calculations were carried out at the M06/6–311G** and MP2/6–311++G**//M06/6–311G** levels with the 6–311G** basis set.

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来源期刊
Journal of Organometallic Chemistry
Journal of Organometallic Chemistry 化学-无机化学与核化学
CiteScore
4.40
自引率
8.70%
发文量
221
审稿时长
36 days
期刊介绍: The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds. Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome. The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.
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