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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.
Typical simple aromatic compounds are benzene, indole, and pyridine. [1] [2] Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene.
This difference is partly related to the lower symmetry of the individual pyridine molecule (C 2v vs D 6h for benzene). A trihydrate (pyridine·3H 2 O) is known; it also crystallizes in an orthorhombic system in the space group Pbca, lattice parameters a = 1244 pm, b = 1783 pm, c = 679 pm and eight formula units per unit cell (measured at 223 K).
Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinoline, benzothiophene, indole, and benzofuran, respectively. The fusion of two benzene rings gives rise to a third ...
Typical examples of basic aromatic rings are pyridine or quinoline. Several rings contain basic as well as non-basic nitrogen atoms, e.g. imidazole and purine. In non-basic aromatic rings the lone pair of electrons of the nitrogen atom is delocalized and contributes to the aromatic pi electron system.
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH 2) 4 NH. It is a cyclic secondary amine, also classified as a saturated heterocycle.
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It was later extended to conjugated molecules such as pyridine, pyrrole and furan that contain atoms other than carbon and hydrogen (heteroatoms). [4] A more dramatic extension of the method to include σ-electrons, known as the extended Hückel method (EHM), was developed by Roald Hoffmann.