Collect. Czech. Chem. Commun. 1981, 46, 2404-2409

Contribution to the study of inductive effect transmission in pyrrole derivatives

Miroslav Jandaa, Jan Šrogla, Petr Holýb and Marie Jakoubkovác

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
b Institute of Haematology and Blood Transfusion, Prague 2
c Institute of Chemical Process Fundamentals, Czechoslovak Academy of Sciences, 165 02 Prague 6-Suchdol


Transmission of the inductive effect in pyrrole derivatives was investigated on 2-ethylpyrrole (VIa), 2-methylpyrrole (VIb), 2-dimethylaminomethylpyrrole (VIc), 2-hydroxymethylpyrrole (VId), methyl 2-pyrrolylacetate (VIe), 2-pyrrolylacetonitrile (VIf), 2-benzenesulfonylmethylpyrrole (VIg) and trimethyl(2-pyrrolylmethyl)ammonium iodide (VIh), by comparison of their relative basicities and acidities. These were determined by IR spectroscopy from the strength of donor-acceptor interactions of the pyrrole derivatives with suitable standard compounds. The found differences show good linear correlations with the σI substituent constants. On this basis, the transfer of the inductive effect in the given pyrrole series appears to be proportional.