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I know that when there are like charges on a resonating structure, the farther apart they are, more stable is the structure due to reduction in repulsive forces.Is the same true for opposite charges? which structure is more stable -
1)with positive charge on one C and negative on adjacent C
2)with positive charge on one C and negative charge on C separated by 4 carbons between them?

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  • $\begingroup$ I haven't seen this before but i think a hydrogen will shift from the positively charged carbon to the negative carbon... Thus neutralising both charges $\endgroup$ – ULTIMATEGAMER07 Dec 17 '17 at 8:35
  • $\begingroup$ In general, the stability of resonating structure is of important within the hybrid of resonance. From a purely electrostatic point of view distance improves stability. A very long dicarboxyloc acid should have just a pKa value, to give you an idea. As far as I know the importance of the zwitterions you described should be negligible anyway.... $\endgroup$ – Alchimista Dec 17 '17 at 13:13
  • $\begingroup$ A carbon with a negative charge adjacent to carbon with a positive charge will form a pi bond. $\endgroup$ – Smap Oct 9 '20 at 17:50
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The answer is 1) when positive and negative charges on C atoms are adjacent.This is because in the second Resonating Structure the charges have to be seprated and as both charges are opposite in nature they will attract each other and make the process of seprating them difficult making it unstabilized.

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Criteria to determine stability of resonating structures in decreasing priority are listed below :

  1. Neutral resonating structures with complete octets are most stable
  2. Ionic resonating structures with complete octets of all atoms is the next criteria to determine stability of resonating structures
  3. Ionic structures in which carbocations are present (with incomplete octets) having unlike charges closer, is ranked at the third priority to determine stability.
  4. Finally, anions at more electronegative element are more stable.

So, according to the information you have provided, the resonating structure which corresponds to the first case is more stable (following the third point)

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