- Joined
- Apr 24, 2011
- Messages
- 127
- Reaction score
- 0
I was hoping someone here might be able to clarify this little conceptual conundrum I'm having:
I understand that larger atoms will produce stronger acids than smaller atoms in the same group, such as H-Br vs H-F, because the negative electric charge is distributed through more space in the anion Br-.
Why then is it that an for hybridization, acid strength is sp > sp2 > sp3 ?
Hybrid orbitals that have more s character are smaller, so the negative electric charge on the conjugate base is more tightly concentrated in the case of an sp hybridized orbital than in the case of an sp3 hybridized orbital. Doesn't this logic contradict the reasoning for larger atoms being stronger acids?
I understand that the strength of an acid comes from the ability of the conjugate base to stabilize its negative charge, but I don't understand why an sp hybridized atom is more stabilizing than an sp3 hybridized atom.
I understand that larger atoms will produce stronger acids than smaller atoms in the same group, such as H-Br vs H-F, because the negative electric charge is distributed through more space in the anion Br-.
Why then is it that an for hybridization, acid strength is sp > sp2 > sp3 ?
Hybrid orbitals that have more s character are smaller, so the negative electric charge on the conjugate base is more tightly concentrated in the case of an sp hybridized orbital than in the case of an sp3 hybridized orbital. Doesn't this logic contradict the reasoning for larger atoms being stronger acids?
I understand that the strength of an acid comes from the ability of the conjugate base to stabilize its negative charge, but I don't understand why an sp hybridized atom is more stabilizing than an sp3 hybridized atom.