Molecule 6

H­­­­­X

Ppm

Integration

Explanation

Ha  

8.06-7.45

5

This is the aromatic region and these are the only aromatic hydrogens.

Hb 

5.29

1

This hydrogen is bonded to the most electron deficient carbon, meaning it will be the most deshielded. Also it has 2 unique neighbors forming a dd.

Hc 

1.22

3

The paper lists these as part of the i-pr group, and it is is the higher of the 2 methyls because it is closer to the oxygen on the ring, causing deshielding.

Hd

1.18

3

Listed as the other methyl hydrogens on the i-pr group.

He

1.65

3

This is the only methyl that is not part of a special functional group of the molecule, so it was simply listed as CH3 in the paper.

Hf

3.83

3

These are listed as being part of the CH2O2C group and is higher down field because it they are on an electron deficient carbon.

Hg

3.95

1

Listed as the only solitary H in the i-pr group.

Hh

2.69

1

Listed as the only OH in the molecule.

Hl

3.75-3.80

1

This is listed as a multiplet and it has the most 3 bond neighbors of any of the other hydrogens.

Hj

4.11

1

This is listed as part of a pair on the same carbon, it was given the higher value because it is cis to a neighboring oxygen, causing greater deshielding.

Hk

4.05

1

This was also listed as being on the same carbon as J however it is trans to the oxygen to it was given the lower ppm.

Hl

4.59

1

This was found by process of elimination, as I believe it is the most deshielded of the remaining hydrogens.

Hm

4.18

1

Next most deshielded

Hn

3.42

1

Last remaining hydrogen, however the paper claims it must be a singlet, it has neighbors, and I actually couldn’t find an appropriate hydrogen to give a singlet peak, this may mean I have interpreted the structure incorrectly.

Molecule 21

Hx

Ppm

Integration

Explanation

Ha

8.04-7.29

10

These are all 10 aromatic hydrogens, falling into the aromatic region of the HNMR spectrum.

Hb

5.34

1

This is labeled in the paper as the CH-Ph hydrogen

Hc

3.83

3

These are listed as the 3H’s in the Acetyl group

H­­d

2.30

1

This is listed as the sole alcohol hydrogen in the paper, and the appropriate deshielding is observed.

He

1.66

3

This is listed as the only methyl group in the paper.

Hf

1.21

3

This is listed as one of i-pr methyl hydrogen groups bur it is closer to a neighboring O so I gave it a higher ppm.

Hg

1.05

3

This is listed as the other set of i-pr methyl hydrogens

Hh

5.53

1

This the most deshielding of the none aromatic H’s and I Place in the same place as for molecule 6. It is still bonded to a carbon that is connected to two oxygens, making it highly electron deficient.

Hi

5.21

1

This is consider to be the next most deshielded hydrogen because of its proximity to the N3.

Hj

4.63

1

We believe this to be next on the chain of electron deficient carbons because it is bonded to carbon that is bonded to a single oxygen. Making it moderately deshielded.

Hk

4.36

1

We believe this to be the least deshielded carbon of those single C-H hydrogens remaining

HL

4.19-3.99

4

Here the paper lists 4 hydrogens displaying multiplets as being in this range I so I chose the 4 that appeared to be the most deshielded and contain multiplets.

Hm

3.97-3.84

3

There are three hydrogens in this range displaying multiplets and they appear to be less deshielded that those in group L.

Hn

3.51-3.37

4

these are the remaining 4 hydrogens that the paper placed into a group with ppm from 3.51-3.37.