# Diazotization order

I know that diazotization of amines proceeds via the generation of the electrophile $$\ce{NO+}$$ and thereafter, the $$\ce{NH2}$$ group acts as a nucleophile and shares it's charge density with $$\ce{NO+}$$. After a series of rearrangements the diazonium salts are obtained. However, if one had to compare the ease/ rate of diazotization, what should we look at?

1. The nucleophilic nature of the $$\ce{NH2}$$ group and it's ability to share it's electron density?
2. Or something else?

As an example if we had the following compounds (see following diagram):

So how would we compare the Diazotization and what would be the order? I compared the nucleophilicity and got the order as: 1-aminocyclohexanoic acid < 2-aminoacetophenone < m-acetoxyaniline < aniline.

• $\ce{NO+}$ is not the nucleophile here. Feb 21, 2020 at 19:31
• It is not just about the nucleophilicity. You need to consider the stability of the diazo compound produced. You don't see too many alkyl diazo compounds., they're not stable. Feb 21, 2020 at 19:44
• Why do you say that NO+ is nucleophile ? It is not Feb 21, 2020 at 20:13
• My sincere apologies, I meant electrophile. Editing it right away. Feb 22, 2020 at 3:55
• @Waylander can you please answer this question and explain how do we proceed to check the stability of the diazonium salts obtained and also do we not look at the nucleophilic nature of the NH2 group altogether? I understand that there is nothing like ignoring all together in chemistry, but is it like the stability of the product is the dominating factor and there's no need to look into the mechanism? Feb 22, 2020 at 4:15