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Abstract
The molecular structure of 2-nitroresorcinol has been determined by electron diffraction in the gas phase. The formation of strong intramolecular hydrogen bonding between the nitro group oxygen and hydroxy hydrogen is indicated by the short H---O nonbonded distance, 1.76±0.04 A. The O---O nonbonded distance (between the nitro and hydroxy groups), 2.56±0.01 A, is also much shorter than twice the oxygen van der Waals radius. The hydrogen bond makes a 110.5±1.5 o angle with the N=O bond corresponding to the direction where one of the oxygen lone pairs of electrons is anticipated. There are considerable bond length changes, as compared with nitrobenzene and phenol, consistent with strong resonance-assisted hydrogen bonding
Published Version
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