Why Is NH3 A Nucleophile In NH3+CH3 -> H3NCH3

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Learn more about Teams Why is NH3 a nucleophile in NH3+CH3 -> H3NCH3 Ask Question Asked 8 years, 3 months ago Modified 8 years, 3 months ago Viewed 7k times 2 $\begingroup$

In the image below:

$\ce{NH3}$ has no charge as it has a full octet.

$\ce{CH3}$ needs 2 more electrons to form a full octet, so has a positive charge.

Why does $\ce{N}$ of the $\ce{NH3}$ want to bond with the $\ce{C}$, even though $\ce{N}$ already has a full octet and neutral charge, and bonding would make it have a negative charge?

Is it because $\ce{N}$ is more electronegative than $\ce{C}$ ?

• electrons
• electronegativity

Share Cite Improve this question Follow edited Aug 21, 2016 at 6:57 K-Feldspar asked Aug 20, 2016 at 21:08 K-FeldsparK-Feldspar 2,8511313 gold badges4545 silver badges6666 bronze badges $\endgroup$ 1

• 1 $\begingroup$ In that picture it’s more like C (which is $\ce{CH3+}$ in there) wants electrons so badly that it’ll get them for crying loudly enough. $\endgroup$ – Jan Commented Aug 20, 2016 at 21:15

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When working with nucleophiles and electrophiles, it is easier to think of them as "positive-ophiles" and "negative-ophiles" respectively.

With that said, NH3 (ammonia) has a lone pair of electrons that is attracted to positive charges. The carbon atom with three bonds is electron deficient and positively charged (which your image does not show). Thus, as a "positive-ophile"/nucleophile, the ammonia through its lone pair is attracted to and forms a bond with the positively charged CH3+ ion.

Yes, nitrogen does have a full octet, but its lone pair of electrons is nonetheless still attracted to the electron deficient and positively charged CH3+ ion. This is similar to how water molecules (also fully satisfied octets) can bind with positively charged sodium ions in solvation process of salt.

Share Cite Improve this answer Follow edited Aug 21, 2016 at 10:42 user33968 answered Aug 21, 2016 at 4:07 HowsikanHowsikan 36411 silver badge66 bronze badges $\endgroup$ Add a comment | 1 $\begingroup$

It's all about thermodynamics. The decrease in energy brought about by filling the carbon octet is larger in magnitude than the increase in energy caused by having a positive charge on the nitrogen atom (it is positive since the total charge of the system must stay the same). This means the sum of the energies of the products is lower than the sum of the energies of reactants, so the reaction is spontaneous.

Share Cite Improve this answer Follow answered Aug 21, 2016 at 4:34 m3wolfm3wolf 19644 bronze badges $\endgroup$ Add a comment |

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