The family member nucleophilicity that amines doesn’t acquire a many coverage (translation: doesn’t obtain tested) in many organic chemistry courses, but if we’re going to cover amines, it appears worthwhile to at least devote one article to your nucleophilicity trends.
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Most that what follows shouldn’t come as a an excellent surprise, as it will certainly echo a many concepts and also themes that have actually made vault appearances in the course (Org 1 in particular). Over there are, however, a couple of interesting wrinkles which might help to put some that these concepts into a broader focus.
Table that Contents
1. A rapid review: Basicity vs. Nucleophilicity
“Um, just how are basicity and also nucleophilicity different again“? you can ask. Always a good question, because sometimes that takes pull close the topic from a few different angle to really make it sink in. Here, we’ll look in ~ it native the view of amines, but a the majority of the ethics are general.
When Is one Amine dubbed A “Base” vs. When Is an Amine referred to as A “Nucleophile”?When an amine reaction to form a bond through a proton (H+) we say the is acting together a base. (A Brønsted base, specifics if you want to tie it back to a familiar concept from basic chemistry). The reactive companion of a basic is referred to as an “acid”, “Brønsted acid”, or merely a “proton”.When one amine reacts to kind a shortcut with any atom other than H, we say it is acting as a nucleophile. The reaction companion is referred to as an electrophile.
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In this article we’re mainly discussing nitrogen nucleophiles and also carbon electrophiles, however when dealing an ext broadly ~ above the subject of nucleophilicity the problem of orbit overlap between orbitals on different rows that the regular table deserve to arise. Sometime in the future we can attend to hard soft acid base (HSAB) theory. Top top the other hand, in ~ a lecture I saw Mayr give once top top his reactivity tables, he to be asked whereby hard and also soft acid-base theory effects were in his data. His prize was, “I don’t know”, through which he meant, he believed his data doesn’t it seems ~ to support it.