Aniline vs. Amine Definition

Quick question-- why does 2-amino pyrrole pass the "match aniline" case, but 2-amino THF not pass the "match amine" case?





2-amino pyrrole


Nc2cccn2





2-amino THF


NC1CCCO1





Aniline Case:


[c:1][NX3;!$(NC~[!#1!#6]):2]





Amine Case:


[#6X4:1][NX3;!$(NC~[!#1!#6]):2]











The reaction in question is a reductive amination, where I'm using the reactivity expression:





(match(ratom(1), amine, 2) || match(ratom(1), aniline, 2)) && !match(ratom(1), "[nH1]")








I would think [!$(NC~[!#1!#6]):2] would fail for both, since the beta atom is N for the pyrrole and O for the THF (at least, I think that's what that reads- I'm still fairly new to the world of SMARTS). However, the software is reacting the pyrrole (at the correct N), but not the furan.


Any help would be appreciated. Thanks.

Due to the highlighted aliphatic carbon atom, that does not prevent matching in case of the aminofurane and aniline query.


[c:1][NX3;!$(NC~[!#1!#6]):2]





So try this use [#6] there instead of the aliphatic C if you would not like to match tthis molecule as a aniline. However this brings the question, anyway, that what results would you expect from amine and aniline queries in case of these molecules?

Gyuri wrote:

Due to the highlighted aliphatic carbon atom, that does not prevent matching in case of the aminofurane and aniline query. [c:1][NX3;!$(NC~[!#1!#6]):2] So try this use [#6] there instead of the aliphatic C if you would not like to match tthis molecule as a aniline. However this brings the question, anyway, that what results would you expect from amine and aniline queries in case of these molecules?

That did it. Thanks- it's getting a little easier as I play around with it.





As for the results, I'm simply shooting tests at the software to practice with my own problem solving with the software. I was simply trying to test a scenario where there was a nitrogen adjacent to a C-O that wasn't necessarily a carbonyl, regardless of reactivity.





Thanks!