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Unlike aromatic compounds, which follow Hückel's rule ([4n+2] π electrons) [1] and are highly stable, antiaromatic compounds are highly unstable and highly reactive. To avoid the instability of antiaromaticity, molecules may change shape, becoming non-planar and therefore breaking some of the π interactions.
In organic chemistry, thiepine (or thiepin) is an unsaturated seven-membered heterocyclic compound, with six carbon atoms and one sulfur atom. The parent compound, C 6 H 6 S is unstable and is predicted to be antiaromatic.
The compound is the prototypical antiaromatic hydrocarbon with 4 pi electrons (or π electrons). It is the smallest [n]-annulene ([4]-annulene).Its rectangular structure is the result of a pseudo [3] - (or second order) Jahn–Teller effect, which distorts the molecule and lowers its symmetry, converting the triplet to a singlet ground state. [4]
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 from conjugation alone.
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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 ...
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