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Dissolution of 2,6-dibromo-4-nitrophenol in aprotic protophilic solvents forms a three-center solvation H-complex with a sharply weakened intramolecular hydrogen bond. This weakening is associated with a deformation of the bond angle of the hydroxy group. It is only on interaction with weak p-bases that the intramolecular component of the bifurcate hydrogen bond appreciably affects the spectral position of the OH stretching vibration band; this results in a nonlinear dependence between vOH and the Kamlet3Taft solvatochromic parameter.In work [2], based on a phenomenological notion of complexes with a bifurcate (three-center) hydrogen bond comprising both an intra-and an intermolecular components, has predicted the effect of the formation energy of such complexes on their n XH vibration frequency. For compounds with a weak intramolecular hydrogen bond, two possibilities have been predicted: a monotonic nonlinear or nearly linear dependence of n XH on the H-bond affinity the subunit of the complex.To test this hypothesis, in the present work we have studied 2,6-dibromo-4-nitrophenol, a compound with a weak intramolecular OH...Br bond [3315], by means of IR, NMR, and UV spectroscopy and quantum chemistry.

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