Tautomerism in the series of acetylpinacolin acylhydrazones
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6035614
It was shown by PMR spectroscopy that acetylpinacolin acylhydrazones exist in deuterochloroform and deuterodimethyl sulfoxide solutions as mixtures of the hydrazone, enehydrazine, and cyclic 5-hydroxypyrazoline forms. In the series of acetylpinacolin aroylhydrazones the introduction of electron-withdrawing substituents into the aromatic ring of the N-aroyl radical shifts the ring-chain tautomeric equilibrium toward the 5-hydroxypyrazoline form. In the series of products from the condensation of acetylpinacolin with the hydrazides of aliphatic acids the proportion of the open-chain tautomer increases with increase in the size of substituent in the N-acyl part.
- Research Organization:
- A.A. Zhdanov Leningrad State Univ., USSR
- OSTI ID:
- 6035614
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:12; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
AZOLES
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CONFIGURATION INTERACTION
CONFORMATIONAL CHANGES
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DMSO
ELECTRON DENSITY
ELECTRONIC STRUCTURE
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRAZINE
HYDRAZONES
HYDROGEN COMPOUNDS
HYDROGEN TRANSFER
HYPERFINE STRUCTURE
ISOMERIZATION
ISOMERS
ISOTOPIC EXCHANGE
MOLECULAR STRUCTURE
NITROGEN COMPOUNDS
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PYRAZOLES
PYRAZOLINES
SPECTRA
STEREOCHEMISTRY
SULFOXIDES
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
AZOLES
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CONFIGURATION INTERACTION
CONFORMATIONAL CHANGES
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DMSO
ELECTRON DENSITY
ELECTRONIC STRUCTURE
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRAZINE
HYDRAZONES
HYDROGEN COMPOUNDS
HYDROGEN TRANSFER
HYPERFINE STRUCTURE
ISOMERIZATION
ISOMERS
ISOTOPIC EXCHANGE
MOLECULAR STRUCTURE
NITROGEN COMPOUNDS
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PYRAZOLES
PYRAZOLINES
SPECTRA
STEREOCHEMISTRY
SULFOXIDES