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Date: 5-8-2018
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Date: 10-5-2017
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Date: 27-9-2020
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A ring that does not have a loop of π electrons and is extremely unstable is said to be antiaromatic. A compound whose molecule contains one or more antiaromatic rings is called an antiaromatic compound. The rings in 1 and 6 are antiaromatic. 1 can be isolated only in an inert, solid matrix (helium, argon, etc.) at temperatures approaching absolute zero. Under all other conditions, it dimerizes rapidly.
Experiments have shown that the ring in 1 is not a square but a rectangle, which is evidence that the ring in 1 does not have a loop of π
electrons. According to molecular orbital theory, 1 is a diradical, which is consistent with its extreme reactivity. 6 has never been observed.
All antiaromatic rings share two features:
Large and, therefore, flexible rings whose Lewis structure suggests a loop of π
electrons containing 4n number of electrons avoid being antiaromatic by deviating from planarity.
e.g.:
Experimentally, 3 is about as stable as any typical alkene, meaning 3 is not antiaromatic. There are no antiaromatic rings containing more than five atoms in the ring.
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