Identifying nucleophiles and electrophiles in an acid-base reaction

Question

Is ammonia a nucleophile and hydrogen the electrophile in the Brønsted-Lowry acid-base reaction of acetic acid with ammonia? $$\ce{CH3COOH + NH3 <=> CH3COO- + NH4+}$$

I say that ammonia is the nucleophile because I drew a curved arrow from the lone pair on the ammonia to the ionizable hydrogen on acetic acid, and I drew a curved arrow from the bonding pair in the hydroxyl group to the oxygen in the hydroxyl group of acetic acid. It seems that ammonia is the nucleophile because it is attacking the hydrogen proton (a bare proton) and that hydrogen is the electrophile because it likes the lone pair on ammonia.

So if the above is right, this would make ammonia a Lewis base and the hydrogen proton a Lewis acid? Or do we say the entire acetic acid molecule is a Lewis acid?

Answer 1

In my opinion, your statements are both right, this is the IUPAC definition [1]:

Lewis acid: A molecular entity (and the corresponding chemical species) that is an electron-pair acceptor and therefore able to react with a Lewis base to form a Lewis adduct, by sharing the electron pair furnished by the Lewis base. For example:

$$\ce{\underset{Lewis acid}{Me3B} + \underset{Lewis base}{:\!NH_\phantom{3}} -> \underset{Lewis adduct}{Me3\overset{-}{B}-\overset{+}{N}H3}}$$

You can see that the author says molecular entity (atom, molecule, ion, ion pair, radical, radical ion, complex, conformer etc., identifiable as a separately distinguishable entity [1]) and the corresponding chemical species (a boarded concept, that in this case I interpret as the combination of different molecular entity), so I think that the exegesis of this definition is that both the acetic acid and the hydron can be called a Lewis acid. And in fact is what usually all the chemists use.

Reference

1. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by S. J. Chalk. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook.