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Content material:
Chapter I basic 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 resources for Chemistry of Heterocyclic Compounds: Imidazole and Its Derivatives, Part I, Volume 6

Example text

Certain imidrtzoles such as 2-to-hydroxyphenyl) -4,5-diphenylimidezole, 2-(o-liydroxyphenyl j benzimidazole, or 2- (o-aminophenyl) benzimidazole exhibit little association in noa-polar solvents, despite the presence of a free imino group. This observation is explicable in terms of intramolecular hydrogen bonding. The formation, through hydrogen bonding, of a quasi-six-membered ring between the ortho substituent and one of the imidazole nitrogens, as illustrated for 2-(0-hydroxyphenyl) benzi- midazole, may successfully compete with the formation of the abovementioned association complexes.

Such a formulation offers a plausible explanation €or the non-association of the imidazoles in polar solvents. N H H H H H 1 I H H H H - . H - - N ~ N . M - ~ ~ ~ . E Z - \NN . I I - A N . E I - - N H N-H... H-NAN... I H- tH tH -H iH HH H H H K H H H H H shape of the aggregates are unknown; however, the observed increase of the specific viscosity with concentration of benzene solutions of imidazole indicates the presence of long-chain polymers. Certain imidrtzoles such as 2-to-hydroxyphenyl) -4,5-diphenylimidezole, 2-(o-liydroxyphenyl j benzimidazole, or 2- (o-aminophenyl) benzimidazole exhibit little association in noa-polar solvents, despite the presence of a free imino group.

Ratios of Isomers Formed on Methylation of Imidaaoles under Varying Conditions" Methylation pwcediire LfelSO4 Compound hfe&Or and alkali A g salt with Me1 Disaomethane Refu 4(or 5)-Methylimidaeole. . . . . . 2b 4(or 5)-Cyanomethyl. . . . . . . 1:6 4(or 5)-Phengl-. . . . . . . . . . 4(or 5)-Bromct. . . . . . . . . . 34:I. 4(or 5)-Nitm.. . . . . . . . . . 350:1 4(0r 5)-Ndro-%methyl-. 50: 1 4(or 5)-ivilr&(or 4)-methyl-. . . 233: 1 4(or 5)-ivdro-5(or 4)-bromo-.

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