Benzyne consists of three resonance forms (aryne, cumulene and diradical). Is benzyne itself aromatic? And what about its triple bond and diradical forms?

  • 1
    Additional bonding doesn't interfere much, as it's not conjugated. Also it's not really diradical. – Mithoron Oct 17 at 18:21
  • Yes, but benzene-1,3-diyl and benzene-1,4-diyl are diradicals. Are they aromatic? – Reijo J Toivola Oct 19 at 7:22
  • Keep in mind that the resonance "forms" of benzyne do not exist as such; benzyne has a single ground state that can be described as a hybrid between these three resonance structures. Benzyne, as well as 1,3-benzenediyl and 1,4-benzenediyl, all are aromatic since they have a 6-electron cyclic conjugate pi bonding system. The nonbonding electrons of the diradicals and the partial pi bond of benzyne all lie in orbitals that are orthogonal to the aromatic pi system, and do not interact appreciably with it. – iad22agp Oct 19 at 14:51

Your Answer

 
discard

By clicking "Post Your Answer", you acknowledge that you have read our updated terms of service, privacy policy and cookie policy, and that your continued use of the website is subject to these policies.

Browse other questions tagged or ask your own question.