Activiating and Deactivating Groups

[Saber tooth]

When on a Benzen Ring, Both NO2 and HSO3 Are meta directors but Which Group is more deactivating NO2 or HSO3?

Another way to look at it is if both groups where on the Benzen Ring... Which would direct?

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[nate28]

When on a Benzen Ring, Both NO2 and HSO3 Are meta directors but Which Group is more deactivating NO2 or HSO3?

Another way to look at it is if both groups where on the Benzen Ring... Which would direct?

Check an o-chem book on this, but I found this website:

http://members.aol.com/logan20/aromatic.html

It says NO2 is stronger than HSO3.

 

[Decan]

No2

 

[Toothguy80]

Why is NO2 a better activator?

Does it have to do anything with their electronegativities?

 

[Decan]

Why is NO2 a better activator?

Does it have to do anything with their electronegativities?

NO2 is a DEACTIVATOR Meta director

 

[hrndawg]

I'm not positive, but I think that NO2 is a stronger deactivator bc there is a positive charge on the N. The argument for meta/op directors is a resonance where in one of the resonance forms, a positive charge will lie on the carbon attached to the functional group if attached o/p. Both SO3H and NO2 are electron withdrawing, so having a positive charge next to them is unstable. Therefore they are both meta directors. However, NO2 is worse, bc that would mean there are two positively charged atoms adjacent to one another.
Because NO2 is a stronger deactivator, SO3H would direct in any further reaction.

 

[VenusFlyTrap]

my book says NO2

 

[Saber tooth]

THank everyone for the help...

my book also said that NO2 is more deactivating and there fore HSO3 would direct