[beheada]

I've got nitrosobenzene here and I'm trying to figure out whether it will be an op director or a meta director. So far, this is what I know about nitrosobenzene.

1)The ring is slightly deactivated by induction via the nitrogen atom which is slightly more EN than the carbon it is attached to.

2)The ring CAN be activated via resonance if the lone pair from the nitrogen decides to hop in, thus making the ring more negative and more reactive toward an electrophile.

3)The ring CAN ALSO BE deactivated via resonance if the ring donates electrons to the nitrogen and the N=O bonding pair goes to the oxygen.

Therefore, in attempting to figure out which type of director it will be, I'm slightly torn.
Meta directors normally have a positive charge (which is possible in one of the resonance forms) yet Ortho/para directors typically have lone pairs they are willing to donate (or they are halogens). Where do I go from here?

BTW - Nitrosobenzene = Benzene + NO

[Dan]

The nitroso is a deactivating O/P directing group (like halogens).

In electrophilic aromatic substitution, you only get meta direction when the substituent in question inhibits O/P attack - ie when a carbocation adjacent to the substituent is destabilised (eg by positive N of a nitro group). If there is a lone pair on the substituent that can stabilise an adjacent carbocation, you get O/P.