Adjacent charge rule

The Adjacent Charge Rule and the Structure of Methyl Azide,... 

The destabilizing effect of the adjacent charge rule shown in covalent nitrates does not occur in the analogous compounds containing carbon as the central atom, such as carbonates, urea, guanidine, etc., since the quadricovalent carbon atom is neutral. 

The adjacent charge rule permits resonance of nitrogen pentoxide among the four structures of type A, but exdudes the four structures of type B (as well as the structure with two double... 

The adjacent charge rule provides some information regarding the nature of the bonds in the oxygen acids of heavier atoms. It has become customary, following Lewis, to assign to the silicate ion and related groups structures... 

Another application of the adjacent-charge rule, to the fluorine nitrate molecule, will be discussed in a following section, with mention also of the stability of covalent and ionic azides and nitrates. 

Note that reaction (a) involves the attack of the soft P atom at the soft carbon atom as predicted by the simple SHAB rule, but reactions (b) and (c) involve the soft atom attacking the hard centres C=0 and P=0 to give products contrary to the general principle (and also in opposition to Pauling s adjacent charge rule (16)). Finally reaction (d) involves the harder nucleophilic atom O attacking the soft electrophile. 

IONIC AND COVALENT AZIDES THE ADJACENT CHARGE RULE... 

The adjacent charge rule and the structure of methyl azide, methyl nitrate, and fluorine nitrate. J. Am. Chem. Soc. 59 (1937) 13—20. (Linus Pauling and L. O. Brockway). SP 59 ... 

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