I was told to remember that formal charges destabilize a resonating structure. But in the following case enter image description hereboth O and N has formal positive charge, how to determine which one is more stable.

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The first canonical form(1) is less stable than the second canonical form(2). Because in the first canonical form the positive charge is over the most electronegative oxygen atom where in second canonical form(2) is over the less electronegative N atom . Point should be noted that the less word has used to mean that the electronegativity of N atom is lesser than oxygen atom.

  • The positive charge is due to formal charge and not due to any vacancy of electrons. I think the second is more stable due to the fact that N has completed its octet while oxygen doesn't. – user66808 Aug 11 at 10:35

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