COSY and HETCOR spectra of Ipsenol

 

COSY and HETCOR spectra Of

1. Ipsenol

1.1 COSY spectrum of ipsenol

chemical shift (ppm)	indicated protons	correlations
6.35	olefinic	coupled to olefinic protons at d 5.08 ppm
5.08 (group)	olefinic	coupled to olefinic protons at d 5.35 ppm and methylene protons at d2.22 and 2.48 ppm
3.83	carbinol methine	coupled to 4 protons corresponding to 2 adjacent methylene groups
2.48	methylene	coupled to carbinol methine proton and each other
2.22	methylene
1.82	isopropyl methine	coupled to 3 protons corresponding to 2 adjacent metnylene groups
1.80	hydroxylic	-
1.49	methylene	coupled to carbinol methine proton and each other
1.26	methylene
0.93	2 overlaping methyl doublets	coupled to isopropyl methine proton

1.2 HETCOR spectrum of ipsenol

13C chemical shift (ppm)	1H chemical shift (ppm)	indicated part of structure
143	-	olefinic (quarternary C)
138	6.35	olefinic
117, 119	5.08, 5.15	olefinic
117	5.24, 5.26	olefinic
69	3.83	carbinol methine
41	2.48, 2.22	methylene
25	1.82	isopropyl methine
-	1.80	hydroxylic
47	1.26, 1.49	methylene
22, 24	0.93	2 overlaping methyl doublets

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COSY and HETCOR spectra of Caryophyllene oxide

COSY and HETCOR spectra

of

Caryophyllene oxide

COSY spectrum of caryophyllene oxide

 Expanded view of COSY spectrum of caryophyllene oxide

       

chemical shift (ppm)	indicated protons	correlations
4.99	olefinic	coupled to each other
4.81	olefinic
2.86	methine	coupled to 2 resonances at 1.28 and 2.23 ppm
2.60	allylic methine	coupled to 3 resonances (methine 1.76 ppm and methylene 1.43, 1.47 ppm)
2.37, 2.11	methylene	coupled to 2 resonances at 2.23 and 1.28 ppm
2.23, 1.28	methylene	coupled to protons at 2.11, 2.37 and 2.86 ppm
2.06, 0.95	methylene	coupled to 2 resonances at 1.45 and 1.63 ppm
1.76	methine	coupled to proton at 1.45 ppm
1.63, 1.45	methylene	coupled to 2 resonances at 0.95 and 2.06 ppm
1.47, 1.43	methylene	coupled to allylic methine at 2.60 ppm
1.19	methyl	-
1.01	methyl	coupled to each other
0.98	methyl

HETCOR spectrum of caryophyllene oxide

        

13C chemical shift (ppm)	1H chemical shift (ppm)	indicated part of structure
153	-	quarternary C-8
113	4.81, 4.99	methylene C-12
63.6	2.86	methine C-5
59.7	-	quarternary C-4
50.9	1.76	methine C-1
48.7	2.60	methine C-9
39.8	1.43, 1.47	methylene C-10
39.2	0.95, 2.06	methylene C-3
34.0	-	quarternary C-11
30.1	1.28, 2.23	methylene C-6
30.0	not available	methyl C-13
29.9	2.11, 2.37	methylene C-7
27.2	1.45, 1.63	methylene C-2
22.6	not available	methyl C-14 or C-15
16.9	not available	methyl C-14 or C-15

COSY cross peak correlations

In a COSY spectrum, a H ¹ spectrum is shown along both horizontal and vertical axes, and the intensity of correlation peaks is shown as mountains.

 The important information from the COSY spectrum comes from the correlation peaks (mountains) that appear off the diagonal (cross peaks). If we start at a given cross peak and imagine that two perpendicular lines lead back to the diagonal, these lines are coupled to each other. 

The intersepted peaks indicate that they are coupled to each other. It is found that the cross peaks above the diagonal are found symmetrically so only cross peaks on one side of the diagonal need to be interpreted.

Example : COSY spectrum of geraniol

1. Basic COSY spectrum of geraniol, in CDCl₃ at 500 MHz

 From the basic COSY spectrum, we can see that H-5 and H-6 are coupled by each other. However, the signals for 3 methyl groups at C-8, C-9, and C-10 are severely overlaped, as are those for the 2 methylene groups at C-4 and C-5. Moreover, it lacks of the H-1----H-4
and H-6----H-8 couplings, and the differentiation between H-8 and H-9 is uncertain.

 These problems can be less by using a double quantum filtered COSY (DQFCOSY); the intense singlets of noncoupled methyl groups are greatly reduced.

2. The DQFCOSY spectrum of geraniol, in CDCl₃ at 500 MHz

 In the DQFCOSY spectrum, we can see that the H-8 and H-9 methyl proton signals are clearly separated. The long-range coupling of H-8 and H-9 methyl groups with one another and the H-1----H-4 and H-6----H-8 couplings are present. However, the differentiation between H-8 and H-9 is still uncertain.

DEPT (Distortionless Enhancement by Polarization Transfer) technique

Proton – coupled ¹³C-NMR spectra are often difficult to interpret due to large coupling constants and overlaping of signals. For this reason, ¹³C-NMR spectra are taken with proton–decoupled mode in which C/H ratios is lost.

To provide this information while retaining signal strength, DEPT (Distortionless Enhancement by Polarization Transfer) is developed.

In DEPT experiments, methyl, methylene, and methine protons can be distinguishable. There are several variations on the experiment.

sub-spectrum	technique
CH	DEPT 90o
CH2	DEPT 45o - DEPT 135o
CH3	DEPT 45o + DEPT 135o - 0.707DEPT 90o
C	comparing the DEPT with the BB decoupled spectrum

The types of carbon observed with various of DEPTs.

1.	DEPT 45o	signals of all protonated carbons
2.	DEPT 90o	signal of CH groups
3.	DEPT 135o	negative signal of CH2, positive signal of CH and CH3, and no signal of C with no attached H

Nomally, only two DEPT experiments are sufficient, DEPT 90^o and DEPT 135^o.

we can distinguish C, CH, CH2 and CH3 because;          - there is no signal of C with no attached H         - CH2 shows negative signal whereas CH and CH3 show positive signal          - CH carbons absorb at lower field and lower signal intensity than CH3carbons

Example 1: DEPT spectrum of isobutyl acetate

Interpretation :

d (ppm)	type of signal in DEPT	represent
22 (b)	positive	2 CH3
24 (c)	positive	CH3
24 (a)	positive	CH
37 (d)	negative	CH2
62 (e)	negative	CH2
170 (f)	not present	C of  >C=O

Example 2: DEPT spectrum of caryophyllene oxide