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How to determine the number of peaks in proton NMR

by egpat      Posted on 09-06-2017

The number of peaks shown by a compound in proton NMR depends on the presence of magnetically non-equivalent protons in the compound.

So in order to predict NMR spectra, we should count protons with different magnetic environment.



Protons may have different chemical and magnetic environment. Here we will see different examples and how we can determine the possible number of peaks in proton NMR. Let’s start with simple structures.


Compounds with different linkage

Organic compounds mainly contain different protons attached at different locations to the parent chain. All these protons are chemically non-equivalent and therefore give different signals NMR spectroscopy.

Protons with different linkage give different NMR signals.

Step 1: Identify the protons with different linkage

Initially observe the structure for protons with different linkage. Protons with same linkage are considered as similar type .

Example 1:

Different types of protons in methane

Here all protons are equivalent as they are similarly connected to carbon.

Hence the number of NMR signals is 1

Remember ! In aliphatic compounds protons attached to same carbon are completely equivalent and therefore give single NMR signal.


Example 2 :

Different types of protons in ethane

In the above example, all the six protons are equivalent as they are connected in similar way to carbon which is connected to another carbon. Here all these protons are primary protons.



Hence again the number of NMR signals is 1


Compounds with configuration

Configuration is the relative arrangement of the atoms or groups within the space. Till now, we have seen simple examples where protons differ by linkage only. These compounds have single configuration in the space.

On the other hand compounds that can show stereoisomerism can exhibit different configuration. Practically many of the important organic and medicinal compounds are unsaturated and therefore show different configuration. Similarly cyclic compounds show geometrical isomerism hence protons lie in different environment.

Here let’s see few examples of aliphatic unsaturated compounds and how to predict NMR signals.

Example 3 :

Different types of protons in propane

Now let’s go to the propane.

Here we can observe two types of protons viz. methyl (-CH3) protons and methylene

(-CH2) protons indicated by ‘a’ and ‘b’ respectively.

The terminal methyl groups are equivalent and labelled as ‘a’.

Hence the number of NMR signals is 2

Step 2: Identify the protons with different configuration (if any)

In the above structure, we can observe two types of protons with different linkage viz. Vinylic (CH2=) proton and=CHCl

Various types of protons in vinyl chloride

If we expand the structure and observe its configuration, we can observe three types of protons.

cis and trans protons in vinyl chloride
  • Proton indicated by a is trans to “Cl” group
  • Proton indicated by a  is cis to “Cl” group
  • Proton indicated by b is adjacent to “Cl”  and attached to same carbon.

Here the protons present on=CH2 are connected equally and they are chemically equivalent.

But they have different configuration hence magnetically non-equivalent.

Magnetically non-equivalent protons give different NMR signals.

  • Hence the total no. of NMR signals possible is “3”

Step 3: Label all magnetically non-equivalent protons

Now indicate all the magnetically non-equivalent protons with letters a,b,c …etc. If protons have same linkage but different configuration they are differentiated by letter prime.

This is already observed in above examples where each magnetically non-equivalent nuclei is indicated by alphabetic letter.

Step 4: Count the protons

Now count all protons which give total no. of NMR signals possible.


Working examples

Let’s apply the above steps with few working examples.

 Working Example 1: Isobutane

Different types of protons in isobutane

Step 1: Here three types of protons are present. Viz. CH3-, CH2-, CH-

 

  • Here all methyl protons are not equivalent.
    • Methyl protons indicated by “a” are attached to “-CH-”
    • Methyl protons indicated by “d” are attached to “-CH2-”
  • Other non-equivalent nuclei are
    • Methine protons (CH) ---- Indicated by “b”
    • Methylene protons (CH2) --- Indicated by “c”

Hence the total no. of NMR signals possible is “4”

 Working Example 2: 2-bromo-4-chloro-3-methylpentane

Different types of protons in 2-bromo-4-chloro-3-methylpentane

Here all protons are not equivalent and give different NMR signals.

  • We can find three methyl protons indicated by a,d and f.
    • a is attached –CHCl-
    • d is attached by –CH-
    • f is attached by –CHBr-
  • Similarly three types of –CH protons indicated by b,c and e.
    • b is attached to –Cl-
    • c is attached to –CH3
    • e is attached to –Br-

Hence total number of NMR signals is 6.

 Working Example 3: Nitro benzene

Different types of protons in nitrobenzene
  • Here three types of protons are present
    • Two Protons indicated by “a” are ortho to nitro (-NO2 ) group
    • Two Protons indicated by “b” are meta to nitro (-NO2 ) group
    • One Proton indicated by “c” is para to nitro (-NO2 ) group
  • Hence the total no. of NMR signals possible is “3”

Here is a video explaining how to determine the number of NMR peaks along with examples.



In this way, we can determine the number of peaks possible for a compound in proton NMR by counting all the protons with different chemical or magnetic environment.




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