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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.
Hückel's rule can also be applied to molecules containing other atoms such as nitrogen or oxygen. For example pyridine (C 5 H 5 N) has a ring structure similar to benzene, except that one -CH- group is replaced by a nitrogen atom with no hydrogen. There are still six π electrons and the pyridine molecule is also aromatic and known for its ...
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.
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.
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 ...
Clar's rule states that for a benzenoid polycyclic aromatic hydrocarbon (i.e. one with only hexagonal rings), the resonance structure with the largest number of disjoint aromatic π-sextets is the most important to characterize its chemical and physical properties. Such a resonance structure is called a Clar structure. In other words, a ...
Basic aromatic compounds get protonated and form aromatic cations (e.g. pyridinium) under acidic conditions. 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.
Electrophilic aromatic substitution (S E Ar) is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration , aromatic halogenation , aromatic sulfonation , alkylation Friedel–Crafts ...