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I am trying to compare the basic strength of two similar amines

Usually this is done by comparing the relative stability of the ion formed on the protonation of nitrogen's lone pair.

This can be done by comparing electronic factors, steric factors, solvation of the ion, etc.

In this example, the stabilisation of the ion due to the +I effect of the groups is the same, as the groups are almost identical.

How will the solvation of the ions formed differ as they have slightly different structures?

Are there other factors that one can consider to help theoretically conclude the relative basicity here?

user55119
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  • "steric factors" (more precisely locked conformation) – Mithoron Nov 26 '23 at 21:37
  • Thing is they are so similar, that it's better to call it a draw and be done with it. Similar amines have little differences in pKa and they are beyond any rules of thumb. – Mithoron Nov 26 '23 at 22:00
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    @Mithoron The data indicates that quinuclidine is more basic than tri ethyl amine, the thread you have linked compares 1-azabicyclo[2.2.1]heptane and tri ethyl amine, where tri ethyl amine is more basic. The explanation provided by the accepted answer would suggest the bicyclo compound being less basic, which is not the case here – mark Nov 27 '23 at 05:40

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