Intramolecular easily polarizable hydrogen bonds with anilides of 1-piperidine carboxylic acids

Add time:08/01/2019    Source:sciencedirect.com

IR spectra are plotted from anilides of 1-piperidine carboxylic acids C5H10N(CH2)n CONHC6H4R in CHCl3 and CDCl3 solutions. In the cases of n = 1 and n = 4, weak intramolecular (NH⋯N) hydrogen bonds are formed. An asymmetrical energy surface occurs and the proton is present at the N of the anilide group. In the cases of n = 2 and n = 3, intramolecular proton transfer hydrogen bonds of the types NBH⋯NP ⇋ −NB⋯H+Np are formed. In contrast to the intramolecular OH⋯ N ⇋ O−1 ⋯ H+N bonds with 1-piperidine carboxylic acids, these bonds to not cause IR continua but two bands: one in the region 3250–3190 and one in the region 2500–2450 cm−1. The fact that, instead of IR continua, bands are observed is explained by the following: (1) these hydrogen bonds are relatively long; (2) they show only a narrow distribution of bond length; (3) the electrical fields at these bonds are small, since they are strongly screened.

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