Chemistry of Heterocyclic Compounds: Imidazole and Its

Content material:
Chapter I normal homes and constitution of the Imidazoles (pages 3–31):
Chapter II The Alkyl? and Arylimidazoles (pages 33–54):
Chapter III The Oxo? and Hydroxyimidazoles and their Sulfur Analogues (pages 55–110):
Chapter IV The Halogenoimidazoles (pages 111–125):
Chapter V The Nitro?, Arylazo?, and Aminoimidazoles (pages 127–173):
Chapter VI The Imidazolecarboxylic and Sulfonic Acids (pages 175–211):
Chapter VII The Imidazolines, 2?Imidazolidones, 2?Imida?Zolidinethiones, 2?Iminoimidazolidines, and Imidazolidines (pages 213–245):
Chapter VIII The Benzimidazoles (pages 247–324):
Chapter IX Imidazoles (pages 327–367):
Chapter X Imidazolines (pages 367–373):
Chapter XI Imidazolidines (pages 373–376):
Chapter XII Imidazolidines, Imidazolidinethiones, and 2?Imidazolidones (pages 376–379):
Chapter XIII Benzimidazoles (pages 379–401):

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Additional info for Chemistry of Heterocyclic Compounds: Imidazole and Its Derivatives, Part I, Volume 6

Sample text

For example, 1-methyl-3-ethylimidazolium iodide affords 1-ethylimidasole and methyl iodide. l-Methyl-3-benzylimidasolium iodide dissociates with the formation of 1-methylimidazole, the benzyl moiety leaving the molecule in the form of benzyl iodide (105-107). This finding is in general agreement with the observed ease with which the hensyl group is removed from other molecules. An electronegative substituent in the 4(or 5)-position of a 1,3-dimethylimidasolium salt weakens the adjacent nitrogen-alkyl bond.

A classical example is the compound 2,4(or, 2,5)-diphenylimidazole. This substance exists in two forms melting at 168' and 1 9 3 O , respectively. The lower melbing modification results from the condensation of a-aminobenzyl cyanide with bemaldehyde and also from the treatment of 2,6diphenyloxazole with ammonia (63),while the higher melting form is obtained from the reaction of benzamidine with m-bromoacetophenone or by the interaction of a-hydroxyacetophenone with benzaldehyde in the presence of ammoniacal cupric acetate (40,64).

Nor do they exhibit the pronounced association whirl1 is so typical of t l w imidazoles (6). * I. General Properties and Structure of Imidamles 23 From an inspection of Table XIV it will be apparent that there is little correlation between the relative magnitudes of the dipole moments and the basic dissociation constants in the mole series. For example, the moments of 1,2,4-triazole and of imidazole are of the same order of magnitude, but their dissociation constants are markedly different. This observation is in disagreement with the postulated amidine resonance which predicts an especially high negative charge on the pyridine nitrogen in azoles exhibiting a high dipole moment.

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