Aryl–perfluoroaryl stacking interactions, hydrogen bonding and steric effects in controlling the structure of supramolecular assemblies of N,N′-diaryloxalamides
作者： Barbara Piotrkowska , Maria Gdaniec , Maria J. Milewska , Tadeusz Połoński
DOI: 10.1039/B709654B
关键词: Hydrogen bond 、 Supramolecular chemistry 、 Intermolecular force 、 Steric effects 、 Aryl 、 Molecule 、 Stacking 、 Crystallography 、 Chemistry
摘要: Cocrystallization of N,N′-diaryloxalamides with pentafluorophenol (pfp) leads to 1:2 molecular complexes, which were characterized by X-ray crystallography. The non-planar oxalamide molecules and pfp assemble into polymeric tapes use the N–H⋯O O–H⋯O hydrogen bonds phenyl–perfluorophenyl interactions, whereas adopting planar conformations form flat trimers held together intermolecular creating two 7-membered rings.
rsc.org
sci-hub.se 参考文章(48)
Y-H Wen, Kun Zhang, X-M Li, Sai Bi, S-S Zhang, None, N,N′‐Bis(3‐methoxyphenyl)oxamide Acta Crystallographica Section E: Crystallographic Communications. ,vol. 62, ,(2006) , 10.1107/S1600536806027802
Yong-Hong Wen, Li-Li Xu, Xue-Mei Li, Shu-Sheng Zhang, N,N′‐Bis(2‐methylphenyl)oxamide Acta Crystallographica Section E-structure Reports Online. ,vol. 62, ,(2006) , 10.1107/S1600536806025992
Venu R. Vangala, Ashwini Nangia, Vincent M. Lynch, Interplay of phenyl–perfluorophenyl stacking, C–H⋯F, C–F⋯π and F⋯F interactions in some crystalline aromatic azines Chemical Communications. ,vol. 2, pp. 1304- 1305 ,(2002) , 10.1039/B202181A
Jonathan C. Collings, Karl P. Roscoe, Edward G. Robins, Andrei S. Batsanov, Lorna M. Stimson, Judith A. K. Howard, Stewart J. Clark, Todd B. Marder, Arene–perfluoroarene interactions in crystal engineering 8: structures of 1∶1 complexes of hexafluorobenzene with fused-ring polyaromatic hydrocarbons New Journal of Chemistry. ,vol. 26, pp. 1740- 1746 ,(2002) , 10.1039/B207102A
Aiwu Sun, Joseph W Lauher, Nancy S Goroff, Preparation of Poly(diiododiacetylene), an Ordered Conjugated Polymer of Carbon and Iodine Science. ,vol. 312, pp. 1030- 1034 ,(2006) , 10.1126/SCIENCE.1124621
Jonathan C. Collings, Karl P. Roscoe, Rhodri Ll. Thomas, Andrei S. Batsanov, Lorna M. Stimson, Judith A. K. Howard, Todd B. Marder, Arene-perfluoroarene interactions in crystal engineering. Part 3. Single-crystal structures of 1 : 1 complexes of octafluoronaphthalene with fused-ring polyaromatic hydrocarbonsFor part 1, see ref. 1. For part 2, see ref. 2. Presented at the 16th International Symposium on Fluorine Chemistry, University of Durham, UK, 16–21 July 2000, Abstract no. 308.Electronic supplementary information (ESI) available: experimental data for the re-determination of the crystal structure of triphenylene, tables of the average bond lengths in OFN and the polyaromatic molecules in both the complexes and pure compounds, and a table of distances and angles for intermolecular H···F contacts in the complexes which are below the sum of the van der Waals radii. See http://www.rsc.org/suppdata/nj/b1/b105502j/ New Journal of Chemistry. ,vol. 25, pp. 1410- 1417 ,(2001) , 10.1039/B105502J
C. R. PATRICK, G. S. PROSSER, A Molecular Complex of Benzene and Hexafluorobenzene Nature. ,vol. 187, pp. 1021- 1021 ,(1960) , 10.1038/1871021A0
Christopher M. Beck, Juan Burdeniuc, Robert H. Crabtree, Arnold L. Rheingold, Glenn P.A. Yap, A ferrocene-perfluoroarene molecular complex Inorganica Chimica Acta. ,vol. 270, pp. 559- 562 ,(1998) , 10.1016/S0020-1693(97)05999-9
Brian Moulton, Michael J. Zaworotko, From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chemical Reviews. ,vol. 101, pp. 1629- 1658 ,(2001) , 10.1021/CR9900432
W. James Feast, P. Wilfried Lövenich, Horst Puschmann, Carlo Taliani, Synthesis and structure of 4,4′-bis(2,3,4,5,6-pentafluorostyryl)stilbene, a self-assembling J aggregate based on aryl–fluoroaryl interactions Chemical Communications. pp. 505- 506 ,(2001) , 10.1039/B100002K