Figure 7
Lobe-HOMO Lewis base hardness and bond length.
The graph shows the to carbenium ion bond length of the anionic Lobe-HOMO array plotted against pKa. The CC bond length associated with ethane, formed when H3C+ complexes with CH3 (a type 15 Lewis acid/base complexation), is of intermediate length, 154 pm.
If the carbenium ion, H3C+, is deemed to be of the same hardness as the carbanion, CH3 then "harder-softer" arguments reverse between FCH3 (hard/soft) and ClCH3 (soft/hard). Therefore, F cannot be congeneric with Cl, Br and I with respect to H3C+.
© Mark R. Leach 1999-2005
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