Helical chirality of 1-phenacyl-1,10-phenanthrolinium bromides |
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Authors: | Florea Dumitraşcu Mino R. Caira Constantin Drăghici Miron Teodor Căproiu Andrei Bădoiu |
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Affiliation: | (1) Institute of Organic Chemistry C. D. Nenitzescu, , Romanian Academy, Bucharest, Romania |
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Abstract: | Evidence for non-coplanarity of the pyridine and pyridinium rings in a series of 1-phenacyl-1,10-phenanthrolinium bromides was gleaned from 1H-NMR data recorded in DMSO-d6 solution. The X-ray structure of 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide, as representative of this series, was determined in order to establish whether such a molecular distortion occurs in the solid state. The title compound crystallizes in the space group C2/c as a sesquihydrate of formula C20H14BrClN2O·1.5H2O with a = 35.7348(3) Å, b = 5.3468(1) Å, c = 21.7312(2) Å, = 116.4076(4)° and Z = 8. In the crystal, the helical chirality is manifested as a pronounced twist in the phenanthrolinium moiety, with the pyridine and pyridinium rings inclined at 6.8(2)°. This distortion is attributed to intramolecular hydrogen bonding of type C–H···N involving the methylene group and the uncharged nitrogen atom of the phenanthrolinium moiety. In the crystal, the cations surround an intricate array of water molecules and bromide ions held together by O–H···Br– hydrogen bonds and comprising infinite chains ···Br–···H–O–H···Br–···, cross-linked by water molecules. |
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Keywords: | Helicity helical distortion 1-phenacyl-1,10-phenanthrolinium bromides X-ray structure 1H-NMR spectroscopy |
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