2,4-Diarylpyrroles: synthesis, characterization and crystallographic insights.

IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY
Mónica Farfán-Paredes, Rosa Santillan
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引用次数: 0

摘要

从 4-硝基丁酮开始合成了三种 2,4-二芳基吡咯,并分析了两种衍生物的晶体结构。它们是 4-(4-甲氧基苯基)-2-(噻吩-2-基)-1H-吡咯(C15H13NOS)和 3-(4-溴苯基)-2-亚硝基-5-苯基-1H-吡咯(C16H11BrN2O)。虽然在 N 原子的 α 位上没有取代基的吡咯对空气非常敏感,而且容易聚合,但我们还是成功地培育出了足够的晶体,用于 X 射线衍射分析。使用亚硝酸钠进一步衍生,得到了亚硝基吡咯衍生物,该衍生物在 Z = 6 的三linic 空间群 P\overline{1} 中结晶。因此,我们在此首次报告了亚硝基吡咯的晶体结构。有趣的是,这种由氮取代的吡咯中的共作用氢键导致了一种三聚体结构,其两端的卤素键分叉,形成了一个具有半径为 5 Å 的间隙空隙的二维(2D)层,这与一些已报道的大环卟啉相似。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
2,4-Diarylpyrroles: synthesis, characterization and crystallographic insights.

Three 2,4-diarylpyrroles were synthesized starting from 4-nitrobutanones and the crystal structures of two derivatives were analysed. These are 4-(4-methoxyphenyl)-2-(thiophen-2-yl)-1H-pyrrole, C15H13NOS, and 3-(4-bromophenyl)-2-nitroso-5-phenyl-1H-pyrrole, C16H11BrN2O. Although pyrroles without substituents at the α-position with respect to the N atom are very air sensitive and tend to polymerize, we succeeded in growing an adequate crystal for X-ray diffraction analysis. Further derivatization using sodium nitrite afforded a nitrosyl pyrrole derivative, which crystallized in the triclinic space group P-1 with Z = 6. Thus, herein we report the first crystal structure of a nitrosyl pyrrole. Interestingly, the co-operative hydrogen bonds in this NO-substituted pyrrole lead to a trimeric structure with bifurcated halogen bonds at the ends, forming a two-dimensional (2D) layer with interstitial voids having a radius of 5 Å, similar to some reported macrocyclic porphyrins.

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来源期刊
Acta Crystallographica Section C Structural Chemistry
Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY
CiteScore
1.60
自引率
12.50%
发文量
148
期刊介绍: Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.
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