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Pyrrole is an extremely weak base for an amine, with a conjugate acid pK a of −3.8. The most thermodynamically stable pyrrolium cation (C 4 H 6 N +) is formed by protonation at the 2 position. Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethylpyrrole has a conjugate acid pK a of +3.7.
Pyrrole-2-carboxylic acid is an organic compound with the formula HNC 4 H 3 CO 2 H. It is one of two monocarboxylic acids of pyrrole. It is a white solid. It arises in nature by dehydrogenation of the amino acid proline. [1] It also arises by carboxylation of pyrrole. [2] The ethyl ester of this acid is readily prepared from pyrrole. [3]
Dissolving Knorr's pyrrole in concentrated sulfuric acid, and then pouring the resulting solution into water will hydrolyze the 4-ester group selectively. The 5-methyl group can be variously oxidized to chloromethyl, aldehyde, or carboxylic acid functionality by the use of stoichiometric sulfuryl chloride in glacial acetic acid. [ 7 ]
1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acid [2]) is a cyclic imino acid. Its conjugate base and anion is 1-pyrroline-5-carboxylate (P5C). In solution, P5C is in spontaneous equilibrium with glutamate-5-semialdhyde (GSA).
Hydrolysis of N-hydroxyphthalimide by the addition of strong bases produces phthalic acid monohydroxamic acid by adding water across one of the carbon–nitrogen bonds. [5] N-Hydroxyphthalimide ethers, on the other hand, are colorless and provide O-alkylhydroxylamines by alkaline hydrolysis or cleavage through hydrazine hydrate.
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Examples of non-basic nitrogen-containing aromatic rings are pyrrole and indole. Pyrrole contains a lone pair that is part of the pi-conjugated system, so it is not available to deprotonate an acidic proton. [1] The basic aromatic rings purines and pyrimidines are nucleobases found in DNA and RNA.
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