Chemistry Heterocyclic Building Blocks Imidazoles 1,3-diphenyl-1H-imidazol-3-ium
Ambeed provide 14 derivatives of 1,3-diphenyl-1H-imidazol-3-ium.
These compounds have the same murcko framework: 1,3-diphenyl-1H-imidazol-3-ium.
Nucleophilic Substitution: The imidazolium ring can undergo nucleophilic substitution reactions. Nucleophiles can attack the carbon atoms adjacent to the positively charged nitrogen atom, resulting in the displacement of one of the phenyl groups. Common nucleophiles include hydroxide ions (OH-), alkoxides (RO-), or amines.
Dehydrogenation: The compound can undergo dehydrogenation reactions, where the hydrogen atoms on the carbon atoms within the imidazolium ring are removed. This can be catalyzed by suitable oxidizing agents, resulting in the formation of a diene or even an aromatic imidazole ring.
Reductive Amination: If you have a suitable reducing agent and an amine, you can perform reductive amination to convert the imidazolium into a secondary or tertiary amine. For example, reaction with ammonia or primary amines can lead to the formation of corresponding secondary or tertiary amines.
Alkylation: The imidazolium ring can be alkylated using alkyl halides or alkylating agents. This can result in the addition of alkyl groups to the imidazolium nitrogen or carbon atoms.
Halogenation: The compound can undergo halogenation reactions where halogens (e.g., Cl2, Br2) can add to the double bonds within the imidazolium ring, resulting in the formation of halogenated derivatives.
Reduction: If you want to remove the positive charge from the imidazolium ring, you can perform a reduction reaction using reducing agents like sodium borohydride (NaBH4) or hydrogen gas H2 in the presence of a suitable catalyst.
Acid-Base Reactions: Depending on the conditions and the nature of the surrounding environment, the imidazolium ion can undergo acid-base reactions with other compounds.
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1,3-Dimesityl-4,5-dimethyl-1H-imidazol-3-ium chloride
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1H-Imidazolium, 1,3-bis[4-iodo-2,6-bis(1-methylethyl)phenyl]-, chloride (1:1)
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1,3-Bis(4-bromophenyl)-1H-imidazol-3-ium bromide
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1,3-Dimesityl-1H-imidazol-3-ium hydrogen carbonate
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1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium tetrafluoroborate
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1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride
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2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride cesium fluoride complex
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1,3-Dimesityl-1H-imidazol-3-ium tetrafluoroborate
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1,3-Bis(4-bromo-2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride
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1,3-Dimesitylimidazolium-2-carboxylate
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1,3-Bis(3,5-dicarboxyphenyl)-1H-imidazol-3-ium chloride
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2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride