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A study of substituent effect on 1 H and 13 C nmr spectra of N ‐ and C‐substituted carbazoles
Author(s) -
Bonesi Sergio M.,
Ponce Maria A.,
ErraBalsells Rosa
Publication year - 2004
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.5570410205
Subject(s) - substituent , chemistry , chemical shift , carbazole , spectral line , nmr spectra database , carbon 13 nmr , computational chemistry , stereochemistry , organic chemistry , physics , astronomy
1 H and 13 C nmr spectra of several N ‐ and C‐substituted carbazoles (Series 1, 2, 3 and 4) were measured. Correlations between chemical shifts and substituent constants show that these parameters describe properly the substituent effect on the nmr phenomena. Atomic charge densities for carbazoles of Series 1, 2, 3 and 4 were calculated by using the semi empirical PM3 method. These values also show a linear correlation with the 13 C chemical shifts. The synthesis of several carbazole derivatives 1a – 1g, 2a – 2g, 3a – 3j and 4a – 4g have been carried out according to literature procedures. The carbazoles 3i, 3j and 4c have been synthesized and fully characterized for the first time.