Issue 11, 1980

An infrared study of the conformations and association of pyrrole-2-carbaldehydes and pyrrole-2-carboxylates

Abstract

The NH and CO bands of solutions of pyrrole-2-carboxylates, pyrrole-2-carbaldehydes, and their N–Me analogues have been studied. Knowledge gained from the spectra of the aldehydes, which are known to adopt the N,O-syn-conformation, was applied in deducing the conformational preferences of the esters from their i.r. absorptions. The N-Me esters exist predominantly or exclusively in the N, carbonyl O-syn-arrangement. With the N–H esters both syn- and anti-rotamers are present, the former predominating, and in the case of t-butyl pyrrole-2-carboxylate the syn-form was shown to be thermochemically more stable than the anti-form by ca. 4.8 kJ mol–1. The intermolecular associations of pyrrole-2-carbaldehyde and of t-butyl pyrrole-2-carboxylate give species containing more than two molecules of the substrates and involve similar enthalpy changes (ca. 22 kJ mol–1).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1980, 1631-1635

An infrared study of the conformations and association of pyrrole-2-carbaldehydes and pyrrole-2-carboxylates

P. T. Kaye, R. Macrae, G. D. Meakins and C. H. Patterson, J. Chem. Soc., Perkin Trans. 2, 1980, 1631 DOI: 10.1039/P29800001631

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