H-NMR Peak

Corresponding H and Explanation

1.47

2- This group is a singlet which is supported by the fact that they are only neighbors to itself. Also, this peak corresponds to 9 H’s, which there are 9 H’s that are all the same. This group is a little less deshielded than group 1 because group 1 has a N=C fairly close to it. This makes group 1 slightly more deshielded than group 2.

1.49

1- This group is a singlet which is supported by the fact that they are only neighbors to itself. Also, this peak corresponds to 9 H’s, which there are 9 H’s that are all the same. This group is slightly more deshielded than group 2 because this group has an N=C fairly close to it while group 2 has a N-C the same distance away. This makes group 2 slightly more deshielded.

2.05-1.99

9- This is deshielded by the fact that it is connected to a tertiary carbon. It has 4 3-bond neighbors which means it should be a multiplet. This is supported by the data. It is fairly far away from the other electronegative atoms which makes it less deshielded than most of the other H’s.

2.80-2.75

8- This carbon is attached to a terciary carbon. However, it is more deshielded than 9 because it is close to the electronegative Cl. Also, it has 4 3-bond neighbors which explains why it is a multiplet on the NMR.

3.44

4- This carbon is attached to a tertiary carbon. However, it is more deshielded than 9 and 8 because it is closer to the electronegative N and could also be slightly affected by the nitrogen 3 bonds away.

3.51-3.50

5- These two H’s are fairly deshielded by the N3 group that is near them. They could have H-bonding with the nitrogens which would explain why it is a multiplet with only one 3-bond neighbor. This group is less deshielded than group 6 which is very similar to it because group 6 has a very electronegative Cl next to it whereas group 5 does not. This implies that group 6 will be more deshielded than group 5.

3.56

14- This is more deshielded than 4 because it is in closer proximity to the C=O group, and the N going into the page. It can have H-bonding with both of these, making it more deshielded than 4. Also, being close to the other N makes it deshielded as well.

3.79-3.72

6- These two H’s are fairly deshielded by the N3 group that is near them. They could have H-bonding with the nitrogens which would explain why it is a multiplet with only one 3-bond neighbor. Also, this group is more deshielded than group 5 which is very similar to it because it is closer to an electronegative Cl which makes it a little more deshielded than group 5.

4.01

7- This H is next to a Cl which makes it about a 3.5, and it is further deshielded by the C=O near it. It is different from 13 because there could be slight H-bonding between 13 and the oxygen near it. This makes 13 a 2-bond neighbor which explains why it is a doublet.

4.07

13- This H is next to a Cl which makes it about 3.5, and it is further deshielded by the C=O near it. It is different from 7 because there could be slight H-bonding between this H and the oxygen near it. This explains why 13 is slightly more deshielded than 7 because it has more interaction with the oxygen. Also, 7 is different from 13 which makes 7 a 2-bond neighbor and explains why 13 is a doublet.

4.17

12- This carbon is attached to a tertiary carbon. It is more deshielded than 9, 8, and 4 because it is close to the Cl and the N. It is also affected by the C=O one bond away from the carbon it is attached to.This makes it much more deshieled than the others.

4.56

10- This H is attached to a carbon that is attached to a secondary carbon and a Cl. This makes it very deshielded. Also, the nitrogen 3 bonds away also could affect it slightly and make it more deshielded.

9.55

3- This H is connected to a very electronegative nitrogen, making it much more deshielded than all of the other H’s because they are all attached to much less electronegative carbons.