4 appended answer 116432 as supplemental, fixed links
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What resonance forms stabilize deprotonated hydroquinone?

Deprotonated hydroquinone looks like this:

deprotonated hydroquinone

Possible resonance forms include:

resonance forms

1 and 2 look reasonable: they don't carry multiple charges. My question is: how much do these two structures contribute to the stability of deprotonated hydroquinone? I am thinking that they should be much higher energy than the structure on top, because the negative charge is on C, which is not nearly as electronegative as O.

Can this be quantified (by and for amateur chemists)?


Per Michael Lautman's suggestion, here are partial charges as calculated in Avogadro:

Avogadro 1

The pattern expected from the resonance forms above, with more negative charge on carbons 2, 4, and 6, is not there.

Why is C4 -0.20?

For comparison, deprotonated cyclohexane-1,4-diol:

Avogadro 2

What resonance forms stabilize deprotonated hydroquinone?

Deprotonated hydroquinone looks like this:

deprotonated hydroquinone

Possible resonance forms include:

resonance forms

1 and 2 look reasonable: they don't carry multiple charges. My question is: how much do these two structures contribute to the stability of deprotonated hydroquinone? I am thinking that they should be much higher energy than the structure on top, because the negative charge is on C, which is not nearly as electronegative as O.

Can this be quantified (by and for amateur chemists)?

What resonance forms stabilize deprotonated hydroquinone?

Deprotonated hydroquinone looks like this:

deprotonated hydroquinone

Possible resonance forms include:

resonance forms

1 and 2 look reasonable: they don't carry multiple charges. My question is: how much do these two structures contribute to the stability of deprotonated hydroquinone? I am thinking that they should be much higher energy than the structure on top, because the negative charge is on C, which is not nearly as electronegative as O.

Can this be quantified (by and for amateur chemists)?


Per Michael Lautman's suggestion, here are partial charges as calculated in Avogadro:

Avogadro 1

The pattern expected from the resonance forms above, with more negative charge on carbons 2, 4, and 6, is not there.

Why is C4 -0.20?

For comparison, deprotonated cyclohexane-1,4-diol:

Avogadro 2

3 added 322 characters in body
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What resonance forms stabilize deprotonated hydroquinone? All I can think of

Deprotonated hydroquinone looks like this:

deprotonated hydroquinone

Possible resonance forms include:

resonance forms

1 and 2 look reasonable: they don't carry multiple charges. My question is putting: how much do these two structures contribute to the lone pair (andstability of deprotonated hydroquinone? I am thinking that they should be much higher energy than the structure on top, because the negative charge) is on the C in para of the deprotonated OH. Is that helpful though? C, which is not particularlynearly as electronegative as O.

deprotonated hydroquinone Can this be quantified (by and for amateur chemists)?

What resonance forms stabilize deprotonated hydroquinone? All I can think of is putting the lone pair (and the negative charge) on the C in para of the deprotonated OH. Is that helpful though? C is not particularly electronegative.

deprotonated hydroquinone

What resonance forms stabilize deprotonated hydroquinone?

Deprotonated hydroquinone looks like this:

deprotonated hydroquinone

Possible resonance forms include:

resonance forms

1 and 2 look reasonable: they don't carry multiple charges. My question is: how much do these two structures contribute to the stability of deprotonated hydroquinone? I am thinking that they should be much higher energy than the structure on top, because the negative charge is on C, which is not nearly as electronegative as O.

Can this be quantified (by and for amateur chemists)?

2 added 2 characters in body
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What resonance forms stabilize deprotonated hydroquinone? All I can think of is putting the lone pair (and the negative charge) on the C in para of the deprotonated OH. Is that helpful though? C is not particularly electronegative.   

deprotonated hydroquinone

What resonance forms stabilize deprotonated hydroquinone? All I can think of is putting the lone pair (and the negative charge) on the C in para of the deprotonated OH. Is that helpful though? C is not particularly electronegative.  deprotonated hydroquinone

What resonance forms stabilize deprotonated hydroquinone? All I can think of is putting the lone pair (and the negative charge) on the C in para of the deprotonated OH. Is that helpful though? C is not particularly electronegative. 

deprotonated hydroquinone

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