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.