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Four peri-substituted naphthalene-1-diazoniurn cations all show short attractive interactions between an electron-rich atom of the peri-substituent and the a-N-atom of the diazonium group. These are interpreted as models for incipient nucleophilic attack on a N r N bond. The diazonium group is a better acceptor of electron density 'through space' than the NO2 group, which parallels their relative 'through-u-bond' inductive effects.

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