Helical chirality of pyrrolo[1,2-a][1,10]phenanthroline derivatives

被引:0
|
作者
F. Dumitraşcu
M. R. Caira
C. Drâghici
M. T. Câproiu
L. Barbu
A. Bâdoiu
机构
[1] Romanian Academy,Centre of Organic Chemistry “C. D. Nenitzescu,”
[2] University of Cape Town,Department of Chemistry
来源
Journal of Chemical Crystallography | 2005年 / 35卷
关键词
Helicity; helical chirality; pyrrolophenanthroline; X-ray structure; H-NMR spectroscopy;
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中图分类号
学科分类号
摘要
The objective of the study was to confirm by X-ray analysis the phenomenon of helical chirality inferred from solution 1H-NMR data for a series of derivatives based on the novel pyrrolo[1,2-a][1,10]phenanthroline system. The syntheses of the title compounds and their 1H-NMR data are presented. Crystals of the representative compound ethyl, 1-(4-phenylbenzoyl)-pyrrolo[1,2-a][1,10]phenanthroline-3-carboxylate, with molecular formula C31H22N2O3, were found to crystallize in the triclinic system, space group P 1 with a = 7.8541(1), b = 11.2605(2), c = 13.4093(3) Å, α = 92.244(1), β = 90.292(1), γ = 106.475(1)∘ and Z = 2. The X-ray analysis revealed the predicted helicity of the phenanthroline system as well as its origin, namely the proximity of the pyridine N atom and the carbonyl C atom of the phenylbenzoyl residue, with non-bonded distance N ⋅s C of only 2.465(2) Å. A secondary, but significant distortion, involving displacement of the carbonyl C atom by more than 0.5 Å from the pyrrole ring, was evident. The crystal structure is maintained by C–H ⋅s O hydrogen bonds and π–π interactions.
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页码:361 / 365
页数:4
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