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Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. In contrast to benzene, the electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom.
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. [3] Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one ...
Two different resonance forms of benzene (top) combine to produce an average structure (bottom). In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone.
Many simple aromatic rings have trivial names. They are usually found as substructures of more complex molecules ("substituted aromatics"). 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.
Aromatization is a chemical reaction in which an aromatic system is formed from a single nonaromatic precursor. Typically aromatization is achieved by dehydrogenation of existing cyclic compounds, illustrated by the conversion of cyclohexane into benzene. Aromatization includes the formation of heterocyclic systems.
One classic reaction is the Chichibabin reaction (Aleksei Chichibabin, 1914) in which pyridine is reacted with an alkali-metal amide such as sodium amide to form 2-aminopyridine. [6] In the compound methyl 3-nitropyridine-4-carboxylate, the meta nitro group is actually displaced by fluorine with cesium fluoride in DMSO at 120 °C. [7]
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Pyrimidine (C 4 H 4 N 2; / p ɪ ˈ r ɪ. m ɪ ˌ d iː n, p aɪ ˈ r ɪ. m ɪ ˌ d iː n /) is an aromatic, heterocyclic, organic compound similar to pyridine (C 5 H 5 N). [3] One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring.