Abstract
The IR spectra of ortho-nitroaniline and methyl anthranilate and their complexes with protonacceptors B have been studied in the region of the stretching vibrations of the NH 2, ND 2 and NHD groups. Weakening of the intramolecular hydrogen bond NH⋯O under the influence of the intermolecular bond NH⋯B has been found to occur. The cooperativity effect increases with the strength of the inter- and intramolecular hydrogen bonds. A method of estimating the intramolecular hydrogen-bond enthalpy in ortho-substituted anilines has been proposed, based on the assumption of the equality of two hydrogen-bond enthalpies in the complex with the symmetrically perturbed amino group. The equivalence of inter- and intramolecular perturbations were determined by the coincidence of cis- and trans-NH (and/or ND) frequencies of the NHD group.
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