I am looking for the reason for the lowest stability of cyclohexane-1,3,5-triimine (D).
I was not able to find any explanation using resonance or aromaticity. All help is appreciated.
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The cyclohexane-1,3,5-triimine tautomer is benzene-1,3,5-triamine, which is aromatic. This makes this trienamine form much more stable than any of the other possible tautomeric forms.
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$\begingroup$ Not really, this question is pretty much nonsense, as all of them are "unstable", whatever this is supposed to even mean... $\endgroup$ – Mithoron Jan 27 '18 at 19:53
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1$\begingroup$ I agree this is clearly a textbook unrealistic question. But my best interpretation was that the condition are such the imines don't solvolyse or anything as such and that the question is about tautomerism (which, I agree, assumes presence of some Lewis bases). $\endgroup$ – Jan Rzymkowski Jan 27 '18 at 19:59
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$\begingroup$ Your answer is not very clear. Why does that make trienamine the least stable? $\endgroup$ – Tan Yong Boon Jan 28 '18 at 2:15
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$\begingroup$ It makes triimine the least stable, because it readily tautomerizes to trienamine, which is aromatic therefore stable. (I'm guessing that in the context of the original question, stable means not transforming into an enamine) $\endgroup$ – Jan Rzymkowski Jan 28 '18 at 18:43
