phenyl groups

[c3p]

they make substances less basic and more acidic compared to their non aromatic cyclic analogs, correct?

ex. cyclohexanol is less acidic than phenol (b/c phenol is res stabilized)

ex. cyclohex--NH3 is more basic than phenyl-NH3 (analine) b/c phenyl is e- w/drawing?

thanks.

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[wantVCUdental]

That's what i thought, and the reasoning behind it is that when the proton is lost (in acids), a negative charge is left, in phenols, that new lone pair can jump in to participate in resonance stabilization. however, in bases, you get a proton that draws away electron density away from the aromatic ring, so it's less stabilizing.