Interpretation of NMR-Spectra

Strategy and Conclusions

Sum formula: Calculate the double-bond equivalents from the sum formula C10H18O.
( 2 * 10 + 2) 18
2

DBE =

=2

-> 2 double bonds - 1 ring und 1 double bond - 2 rings

13

C{1H} :

Number the 13C signals sequencially, starting with No. 1 for the most high
field signal.
10 carbons: Does agree with the sum formula C10H18O. That means: Each
13
C signal corresponds to 1 carbon.
1
2
3
4
5
6
7
8
9
10

CH3
CH3
CH3
CH2
CH2
CH2
CH
CH
C
C

- range

HSQC :

Assign the 1H signals to the corresponding 13C signals.

Copy the numeration of the 1H signals in the HSQC to the 1H spectra.

H:

The integration is not very accurate. H(4) und H(5), each corresponding to
one -CH2 group, are integrating for 5 protons!
H(4) und H(5) are signals of higher order.
Sum formula : The difference to the sum formula is one Proton, an OH. The chemical
shift of this -OH is probably close to the chemical shifts of the signals H(4)
/ H(5).
DQF-COSY :

Label the 1H signals on the F1- and F2-axis.

Put several structure fragments together.
H
C

9/10

C
8

H
C

H
C

H
C

9/10

C
7

H
C

At this moment just 3 methyl groups and the OH group are missing.

HMBC :

Label the 1H signals on the F2-axis and the 13C signals on the F1-axis.
We recommend to make a list of the CH and HC correlations.
13

1
2
3
4
5
6
7
8
9
10

5/OH (6)
7
1/3
8
2
8
5/OH (6)
8
1/3
4
(6)
(7)
1/3 5/OH
6
2
1/3 5/OH
2
1/3
4
1/3 5/OH
4

C(10) => H(6)

C(9) > H(6)
H
C

10

7
9
7
9
7
(5)
(6)
(4)

9 10

8 9 10
10
8 10
7 10

C(9) => H(4) > H(5)

C(10) => H(6)
C(10) => H(4,5)

C(5) => H(7)

C(8) => H(4,5)
C(7) => H(5,OH) > H(4)

5
8
5
8
4
(4)
5
3

2
3
2
5
1
(1)
1
2

1
2
3
4
5
6
7
8

13

C(9) => H(4)

10

C(3) => H(2)

H(8) => C(2,3)
2
H
CH3
C C
9 8
CH3

10

C(1) => H(5,7)

The chemical shift of H(6) is 4.1ppm => -OH is bounded on C(6) .
2/3

CH3
C C
9 8
CH3

2/3

H
C

H
C

CH3 H
C

10

C
7

H
C

OH

1D-NOESY :

H(6) => H(1/3)

H(8) => H(1/3) > H(2)

CH3
C C
9 8
CH3
2

It is Geraniol:

H
C

H
C

CH3
C

10

H
7

C
H

OH