Relative basicity of heterocycles

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Offline ch4ec

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Relative basicity of heterocycles
« on: 31/03/2007 23:23:33 »
Basicly (haha-pun) Im having trouble understanding why the basicity of the heterocycle decreases as a the heteroatom goes down the group. I thought that the increase in size of the heteroatom would decrease lone pair/lone pair repulsion thus increasing stability and so increasing the basicity of the molecule? Why does the basicity decrease as the stability increases????  [O8)]

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Offline rosy

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Relative basicity of heterocycles
« Reply #1 on: 02/04/2007 14:08:43 »
Going down the group, the lone pair orbital on the heterocycle becomes more diffuse and so less able to stabilise the protonated state.