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首页> 外文期刊>Crystal growth & design >Molecular arrangement and photoreaction of sorbamides and hexadienyl carbamates with various N-substituents in the solid state
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Molecular arrangement and photoreaction of sorbamides and hexadienyl carbamates with various N-substituents in the solid state

机译：山梨酰胺和氨基己酸己二酯的分子排列和光反应与各种固态N取代基

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摘要

The crystal structure and solid-state photoreaction of sorbamides and 2,4-hexadienyl carbamates with various N-substituents have been investigated. One-dimensional (1D) hydrogen bond chains with a repeating distance of 5 angstrom were observed in their crystals, due to the strong intermolecular interaction between the CO and N-H groups in the amide and carbamate moieties. We have revealed that N-benzylsorbamide and 2,4-hexadienyl N-(1-naphthyl)carbamate have a molecular stacking structure appropriate for the occurring [2+2] photodimerization and topochemical polymerization, respectively. The former sorbamide derivative gave a cyclodimer with an asymmetric structure, which was determined by NMR spectroscopy, under UV irradiation in the crystalline state. The gamma-radiation of the latter carbamate derivative gave a polymer that is insoluble in any solvent. The polymer structure was determined by powder X-ray diffraction and IR spectroscopy. The reactivity in the solid-state photoreaction was discussed on the basis of the molecular stacking structures such as the stacking distance, the carbon-to-carbon distance, and the overlap of the pi-orbitals. A twisted molecular conformation of the reacting diene planes against the carbamoyl planes connected with each other by the 1D hydrogen bonding is important for topochemical polymerization in the solid state.
机译：研究了山梨酰胺和2,4-己二烯基氨基甲酸酯与各种N-取代基的晶体结构和固态光反应性。由于酰胺和氨基甲酸酯基团中的CO和N-H基团之间强烈的分子间相互作用，在其晶体中观察到了重复距离为5埃的一维（1D）氢键链。我们已经揭示，N-苄基山梨酰胺和2，4-己二烯基N-（1-萘基）氨基甲酸酯具有分别适合于发生的[2 + 2]光二聚和拓扑化学聚合的分子堆叠结构。前者的山梨酰胺衍生物得到具有不对称结构的环二聚体，该结构通过NMR光谱在结晶态的UV辐射下测定。后一种氨基甲酸酯衍生物的γ-辐射得到不溶于任何溶剂的聚合物。通过粉末X射线衍射和IR光谱确定聚合物结构。基于分子堆积结构，例如堆积距离，碳-碳距离和π-轨道的重叠，讨论了固态光反应中的反应性。反应的二烯平面相对于通过一维氢键相互连接的氨基甲酰基平面的扭曲分子构象对于固态拓扑化学聚合是重要的。

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