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Azolides. VII—Restricted rotation in N ‐acylindoles and carbazoles. Anisotropy effect of the carbonyl group
Author(s) -
Elguero José,
Marzin Claude,
Peek Michael E.
Publication year - 1975
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270070910
Subject(s) - steric effects , chemistry , carbazole , anisotropy , rotation (mathematics) , group (periodic table) , internal rotation , carbonyl group , medicinal chemistry , stereochemistry , double bond , computational chemistry , crystallography , photochemistry , organic chemistry , physics , quantum mechanics , mathematics , geometry , mechanical engineering , engineering
Abstract The barrier to internal rotation about the NC bond and the E/Z configuration of some N ‐acetyl and N ‐formylindole derivatives have been determined and discussed in terms of electronic and steric effects. The barriers to internal rotation have been determined for certain N ‐acetylcarbazoles and some new N ‐formyl derivatives of carbazole. Experimental proof is also given, showing that contrary to the provisions of the classical model of carbonyl anisotropy, the protons (α and peri positions) next to the oxygen of the acyl group are displaced to high frequencies. This result allows one to determine the preferred configuration of N ‐acetyl derivatives of perimidine and 1H‐naphtho[1,8‐de]triazine.