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Studies on Enolisation of Some β‐Diketones by Spectrophotometric Method
Author(s) -
Taneja A. D.,
Srivastava K. P.,
Gupta M. C.
Publication year - 1972
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.197200017
Subject(s) - chemistry , acetanilide , formamide , chloroform , dimethylformamide , methanol , aniline , tautomer , medicinal chemistry , organic chemistry , photochemistry , solvent
Abstract Enolisation of acetoacetanilide (AAAH) acetoacet ortho‐toluidide (AATH), 2, 4‐acetoacetxylidide (AAXH), acetoacet‐ortho‐chloroanilide (CAAAH), acetoacetortho‐anisidide (OAAAH), benzoyl‐acetanilide (BAAH) and benzoyl‐meta‐nitro‐acetanilide (NBAAH) have been studied in different solvents of varying polarities, ranging from chloroform (z=63.2) to methanol (Z=83.6) by ultraviolet spectroscopic methods. The low percentages of enol contents in formamide, dimethylformamide and dimethylsulphoxide, may be due to the formation of charge transfer complexes of these solvents with the diketones. Free energy of tautomerisation has also been calculated. The substituents on the phenyl group attached to the nitrogen have no effect on enolisation.