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Friedel‐crafts acylalion of 3‐carboxymethylbenzo[ B ] thiophenes, LIS‐nmr and HOMO study of regioselectivity
Author(s) -
Hannoun M.,
Blazević A.,
Kolbah D.,
Sabljiéa A.,
Trinajstić N.,
Sega A.,
Lisini A.,
Kajfež F.,
Šunjić V.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160539
Subject(s) - chemistry , regioselectivity , friedel–crafts reaction , carbon 13 nmr , nmr spectra database , acetylation , stereochemistry , computational chemistry , medicinal chemistry , spectral line , organic chemistry , catalysis , biochemistry , physics , astronomy , gene
3‐Carboxymethylbenzo[ b ] thiophenes give on benzoylation and acetylation, two pairs of isomers, 2/3 and 4/5, respectively. It is determined by the combined nmr spectroscopic analysis (360 MHz and calculated spectra, LIS‐nmr) and HOMO calculations of the electron densities on positively charged 1, that 2 and 4 are 4‐substituted, while 3 and 5 are 6‐substituted isomers.