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Organic chemistry
Formal charge on nitrogen
How to calculate the formal charge on nitrogen.
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- Why can't we assume that Nitrogen has H bonds (as we did with Carbon in the previous video) instead of lone pairs?(8 votes)
- no, we can't. Because the drawing of a molecule we have seen in last video is a special method to represent carbon compounds known as line structure or skeletal structure. you must've noticed that we don't use the letter C to represent carbon there.(18 votes)
- Atit's said that "it's as though Nitrogen has lost an electron" Where did it go? Did it bond with another atom? Or does it remain as a lone electron in the shell of the original Nitogen buzzing around by itself? Is this why Nitrogen now has a charge of +1? I'm confused! Where do these disappearing electrons go? 05:14(5 votes)
- It didn't really go anywhere, the lone pair on nitrogen in ammonia picked up a hydrogen ion and formed a covalent bond. The consequence of this is now there is one more proton than electrons in the molecule so it has a positive charge.(7 votes)
- How can Nitrogen have a formal charge of zero with two free electrons? I thought that free electrons create a negative charge? Thank you(6 votes)
- Because Nitrogen has 7 protons in its nucleus and 7 electrons around it. 5 of those electrons are its valence electrons, which are located in its outermost energy level. In this case the Nitrogen does not undergo any hybridization, and the free electrons in its 2p orbital form a covalent bond with the Hydrogens and a Carbon, leaving behind the 2s orbital which has 2 unpaired electrons.(5 votes)
- Where did the electrons go/come from in the + and - cases?(3 votes)
- The electrons don’t go anywhere. It's how we count the electrons that makes the difference.
In NH₄⁺, the + charge is smeared over the whole ion, but most of it is on the N.
We count the electrons AS IF they were equally shared between N and H.
This puts ALL the + charge on N and none on H.
Thus, formal charge is an approximation to the actual charge distribution in a molecule or ion.(5 votes)
- Why does N2+O2 --> 2NO
When N has a -3 charge? I thought it was N2O3 but that's not right and I don't understand why(2 votes)- That NO will actually be an cation, therefore NO+
https://en.wikipedia.org/wiki/Nitrosonium(3 votes)
- nitrogen should have formal charge of three because the two s orbital electrons if participate in reaction, it would go totally unstable. Isnt it?(1 vote)
- The valence electrons of nitrogen in its compounds are all sp³ hybridized orbitals.
The formal charge on N is usually -1 for an anion, 0 for a neutral compound, and +1 in cations.
A nitrogen atom with a formal charge of -3 would correspond to a nitride ion, N³⁻, which is strongly basic in aqueous solution.(5 votes)
- I don't really get why, when it's 3 bonds, we assume there is a lone pair, but with 4 bonds, we assume there is not. Why would we not assume there is one lone electron?
Edit: wow, forgot the basics. It is because of the 7 electrons, not just the valence shell right?(1 vote)- In a given structure you should assume that the atoms are going to be following the octet rule, otherwise it would have a charge shown. If that’s the case then nitrogen always has 8 electrons around it at most.
So if you see 3 bonds (=6 electrons) and no charge shown for a nitrogen you know there must be a lone pair to make that 8 electrons.
If you see 4 bonds then that’s already 8 electrons it can’t hold any more.(4 votes)
- A nitrogen atom surrounded by four hydrogen atoms is the ammonium radical (NH4+). What is the name given to NH2-, if any?(2 votes)
- So, we have HCl molecule, where H+ is a cation and Cl- is an anion. H has got 1 electron and it gives it to Cl. If we have NH4+ cation, N has got only 4 electrons, so it takes 1 electron from any anion (like Cl-). Does it mean that cation can take electrons as well as give them? If NH4+ takes 1 electron from Cl that means Cl has got 3 pairs of electrons?(2 votes)
- HCl is not an ionic compound, it's a covalent molecule, a gas at room temperature. It's only in water when it splits up.
NH4+ has a + charge because it is NH3 that has formed a bond with a H+ using the N lone pair. The whole ion has 1 more proton than it has electrons hence the charge. The N still brought 5 electrons to the ion...
Your end bit sounds like rambling, it doesn't make sense.(0 votes)
- atwill there not be a co-ordinate bond from nitrogen 5:13(1 vote)
Video transcript
- [Voiceover] In this video
we'll assign formal charge to nitrogen, and just to remind you of the definition for formal charge, formal charge is equal to the
number of valance electrons in the free atom minus the
number of valence electrons in the bonded atom. Or another way of saying that, formal charge is equal to the number of valence electrons the
atom is supposed to have minus the number of valence electrons that the atom actually has in the drawing. So let's assign a formal
charge to the nitrogen in this molecule. And remember that each bond
represents two electrons. So I'm gonna draw in the
electrons in this bond so it's easier for us to
assign a formal charge to the nitrogen. So formal charge is equal to the number of valence electrons that
nitrogen is supposed to have. We know that nitrogen is supposed to have five valence electrons,
because of its position on the periodic table. So this is five. And from that we subtract the number of valence electrons that
nitrogen has in our drawing. So let's go back over
here to the dot structure and let's look at these bonds. We know that from this
bond here on the left nitrogen gets one of those electrons. And from this bond on the right nitrogen gets one of those electrons and hydrogen gets the other. And same for this nitrogen-hydrogen bond. Nitrogen gets one of the electrons and hydrogen gets the other. So how many electrons do
we have around nitrogen in our drawing? Let's count them up. This would be one, two, three, and then we have a lone pair
of electrons on the nitrogen, so that's four, and five. So in our drawing, nitrogen is surrounded by five valance electrons. So we put five minus five
which is equal to zero. So nitrogen has a formal charge of zero. Let me go ahead and redraw that. So we had our nitrogen
here with our two hydrogens and a lone pair of
electrons on the nitrogen. We found the nitrogen to
have a formal charge of zero. So we have a pattern. Every time that you see
nitrogen with three bonds, let me draw these in here, one, two, three. So three bonds and one
lone pair of electrons, the formal charge is equal to zero. So when nitrogen has three bonds and one lone pair of electrons, the formal
charge is equal to zero. And sometimes you don't want to draw in lone pairs of electrons, so
you could just leave those off. You could just say alright,
well if I just draw this and you know the formal
charge of nitrogen is zero, then it's assumed you also know there's a lone pair of electrons on that nitrogen. So this is just another
way of representing the same molecule,
leaving off the lone pair, because you should know it's there. Let's look at other
examples where nitrogen has a formal charge of zero. So we'll start with the
example on the left here and if we look at this nitrogen and we know it has a
formal charge of zero, let's see how many bonds it has. Let's use red here. So here's one bond, two
bonds, and then three bonds. So three bonds, and with
a formal charge of zero we know there should be
a lone pair of electrons on that nitrogen. So you could leave it off
and just know it's there, or you could draw them in. So I'll go ahead and draw in the lone pair of electrons on the nitrogen. So formal charge of zero. Let's look at the one on the right. So if we assume that nitrogen
has a formal charge of zero, let's see how many bonds we have here. So here's one, two, and three. So we have three bonds, so we'd still need one
lone pair of electrons. So if you wanted to show
the lone pair of electrons you could put them in there like that. Notice this gives nitrogen an
octet of electrons around it. So count those up, here's two, four, six, and eight. So nitrogen would have an octet. And remember, you could just leave off that lone pair of
electrons and it's assumed if we know nitrogen has
a formal charge of zero that there is a lone
pair and we just didn't want to take the time to draw them in. Let's assign formal charge
to another nitrogen, so down here. So what is the formal
charge of nitrogen now? Let's draw in our electrons. So each bond is two electrons, so I draw those in there. And the formal charge on nitrogen is equal to the number
of valence electrons that nitrogen is supposed to have, which we already know is five, so we put a five in here, and from that we subtract the
number of valence electrons that nitrogen actually has in our drawing. So for these bonds,
hydrogen gets one electron and nitrogen gets one
for each of these bonds. So that allows us to see
there are four electrons around nitrogen. So here's one, two, three, and four. So in our drawing, nitrogen only has four electrons around it, so this would be five minus four, which gives us a formal charge of plus one. So it's like nitrogen
lost a valence electron. It's supposed to have five and here we see only four around it, so it's as if it lost a valence electron, so it's plus one for the formal charge. Alright, let me redraw that. So we have our nitrogen
with four bonds to hydrogen and then nitrogen has a
plus one formal charge. You should recognize this
as being the ammonium ion from general chemistry. So this has a formal charge of plus one, so we have another pattern
to think about here. So let's draw that in. We have one, two, three, four bonds and zero lone pairs of electrons. So when nitrogen has four bonds, four bonds and zero lone pairs, zero lone pairs of electrons, we've already seen the formal charge be equal to plus one. So let's look at some examples where nitrogen has a
formal charge of plus one. So the example on the left, we can see there are four bonds and there are no lone
pairs on that nitrogen, so that's a plus one formal charge. Over here on the right, same idea. Here's one bond, two bonds, three bonds, and four bonds and no lone pairs, so a plus one formal
charge on the nitrogen. Alright, finally, one more nitrogen to assign a formal charge to. So let's look at this one. Let's draw in the electrons in the bond. So here's two electrons
and here's two electrons. What is the formal charge on nitrogen? Formal charge is equal to
number of valence electrons nitrogen is supposed to
have, which we know is five, and from that we subtract the
number of valance electrons nitrogen actually has
in our dot structure. So again we go over to here
and we look at this bond and we give one electron to nitrogen and one electron to the other atom. And over here we give
one electron to nitrogen and one electron to the other atom. And now we have two
lone pairs of electrons on the nitrogen. So how many is that total? this would be one, two, three, four, five, and six. So six electrons around our nitrogen. So five minus six gives us negative one. So a formal charge of negative one. Let me go ahead and redraw that. So I could draw it out here. So nitrogen with two
lone pairs of electrons we just found has a formal
charge of negative one. If I wanted to leave off
the lone pairs of electrons I could do that, I
could just write NH here and put a negative one formal charge, and because of this
pattern, you should know there are two lone pairs of
electrons on that nitrogen. Let me just clarify the pattern here. The pattern for a formal
charge of negative one on nitrogen would be two bonds, here are the two bonds, and two lone pairs of electrons. So when nitrogen has two bonds and two lone pairs of electrons, nitrogen should have a formal
charge of negative one. Let's look at some examples of that. So down here we have nitrogen. So here's nitrogen with no lone
pairs of electrons drawn in, but you know this nitrogen
has a negative one formal charge, because it's
telling you that right here. How many bonds do we have? Well here's one bond and here's the other bond. So we have our two bonds, but we don't have our
two lone pairs drawn in. So you could just know
that they are there, or I'll go ahead and add them in here. So here's one lone pair of electrons and here's the other
lone pair of electrons on that nitrogen. Notice that gives that
nitrogen an octet of electrons. Over here on the right,
let's do the same thing. You know this nitrogen has a
negative one formal charge, so you know it must have two bonds and two lone pairs of electrons. So here we can see,
here are the two bonds, so that takes care of the two bonds part, and if it has a negative one formal charge it must have two lone pairs of electrons. So we could draw in those lone pairs, or we could leave them off, depending on what you're trying to show
when you're drawing these out.