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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 ...
This difference is partly related to the lower symmetry of the individual pyridine molecule (C 2v vs D 6h for benzene). A tri hydrate (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).
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 ...
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.
These terms can also be used in six-membered heterocyclic aromatic systems such as pyridine, where the nitrogen atom is considered one of the substituents. For example, nicotinamide and niacin, shown meta substitutions on a pyridine ring, while the cation of pralidoxime is an ortho isomer.
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The lowest triplet state of an annulene is, according to Baird's rule, aromatic when it has 4n π-electrons and antiaromatic when the π-electron count is 4n + 2, where n is any positive integer. This trend is opposite to that predicted by Hückel's rule for the ground state , which is usually the lowest singlet state (S 0 ).