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A simple case study for the introduction of the HMBC and ... · A simple case study for the...
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A simple case study for the introduction of the HMBC and the EI-MS techniques to second and third year undergraduate students. Supplementary Material Esther H. S. Woo, 1 Mackenzie J. Field, 1 Mathew L. Sutherland, 1 Chloe A. N. Gerak 2 * and Nabyl Merbouh 1 * 1. Simon Fraser University, Department of Chemistry, 8888 University Drive, Burnaby, BC, V5A 1S6, Canada. Fax: +(1)‐778‐782‐3765. E‐mail: (*) [email protected] 2. University of British Columbia, Department of Biochemistry and Molecular Biology, 2350 Health Sciences Mall, Vancouver, BC, V6T 1Z3, Canada. Fax: +(1)-604-822-5227. E-mail: (*) [email protected] 3-Phenylbutyric acid (PBA) 1 H-NMR. 13 C-NMR, APT, COSY, HSQC, HMBC, IR, UV and Mass Spectra α-methylhydrocinnamic acid (MHCA) 1 H-NMR. 13 C-NMR, APT, COSY, HSQC, HMBC, IR, UV and Mass Spectra
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Transcript of A simple case study for the introduction of the HMBC and ... · A simple case study for the...
A simple case study for the introduction of the HMBC and the EI-MS
techniques to second and third year undergraduate students.
Supplementary Material
Esther H. S. Woo, 1 Mackenzie J. Field, 1 Mathew L. Sutherland, 1 Chloe A. N. Gerak2*
and Nabyl Merbouh1*
1. Simon Fraser University, Department of Chemistry, 8888 University Drive, Burnaby,
BC, V5A 1S6, Canada. Fax: +(1)‐778‐782‐3765. E‐mail: (*) [email protected]
2. University of British Columbia, Department of Biochemistry and Molecular Biology,
2350 Health Sciences Mall, Vancouver, BC, V6T 1Z3, Canada. Fax: +(1)-604-822-5227.
E-mail: (*) [email protected]
3-Phenylbutyric acid (PBA)
1H-NMR. 13C-NMR, APT, COSY, HSQC, HMBC, IR, UV and Mass Spectra
α-methylhydrocinnamic acid (MHCA)
1H-NMR. 13C-NMR, APT, COSY, HSQC, HMBC, IR, UV and Mass Spectra
-2-1012345678910111213f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
22000
23000
24000
25000
3.0
0
1.0
51.0
41.0
2
3.0
32.0
0
1.1
763
1.1
936
2.6
501
2.6
701
2.6
835
2.7
035
2.7
316
2.7
483
2.7
649
2.7
817
2.8
016
2.8
189
3.0
596
3.0
755
3.0
930
3.1
089
7.1809
7.1977
7.2201
7.2383
7.2765
7.2952
7.3124
9.510.010.511.011.512.012.5f1 (ppm)
11.1
209
MHCA 1H-NMR
6.987.007.027.047.067.087.107.127.147.167.187.207.227.247.267.287.307.327.347.367.387.407.427.447.467.487.507.527.54f1 (ppm)
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
3.0
3
2.0
0
7.1809
7.1977
7.2201
7.2383
7.2765
7.2952
7.3124
MHCA 1H-NMR
1.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.2f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
3.0
0
1.0
5
1.0
4
1.0
2
1.1
763
1.1
936
2.6
501
2.6
701
2.6
835
2.7
035
2.7
316
2.7
483
2.7
649
2.7
817
2.8
016
2.8
189
3.0
596
3.0
755
3.0
930
3.1
089
MHCA 1H-NMR
-100102030405060708090100110120130140150160170180190200210220230f1 (ppm)
-4000
-2000
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
22000
24000
26000
28000
30000
32000
34000
36000
16.5
9
39.3
941.2
4
126.5
2128.5
1129.0
9
139.1
0
182.0
0
MHCA 13C-NMR
125130135140145150155160165170175180f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
22000
23000
24000
126.5
2128.5
1129.0
9
139.1
0
182.0
0
MHCA 13C-NMR
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
-20000
-15000
-10000
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
4500016.5
5
39.3
241.3
3
126.5
0128.4
9129.0
8
139.0
6
182.8
4
MHCA APT
125130135140145150155160165170175180185190f1 (ppm)
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
45000126.5
0
128.4
9129.0
8
139.0
6
182.8
4MHCA APT
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
f1 (
ppm
)
MHCA COSY
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
10
20
30
40
50
60
70
80
90
100
110
120
130
140
f1 (
ppm
)
MHCA HSQC
1.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
f1 (
ppm
)
MHCA HMBC
0.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.53.6f2 (ppm)
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
f1 (
ppm
)
MHCA HMBC
Print Date: 18 Sep 2015 13:44:46
MS Data Review Active Chromatogram and Spectrum Plots - 9/18/2015 1:44 PMFile: c:\varianws\data\girlpower\mhca 7-29-2015 columnei 400 mass.smsSample: MHCA Operator: Scan Range: 1 - 759 Time Range: 0.00 - 11.31 min. Date: 7/29/2015 4:20 PM
2.5 5.0 7.5 10.0 minutes
0
100
200
300
400
500
600
700
800
900kCounts RIC Merged mhca 7-29-2015 columnei 400 mass.sms 4000 CENTROID FILTERED
1A
50 100 150 200 250 300 350 400 m/z
0
50
100
150
200
250
kCounts
45.0 5592
63.0 9718
65.0 38796
77.1 7978
91.0 296123
92.0 22064
95.0 277
115.0 13126
118.0 45546
131.0 7594 147.0
2852
164.0 47398
164.9 7194 182.8
239 200.0 255
219.2 20
233.1 166
249.3 167
265.1 29
281.1 35
311.1 6
339.9 20
356.9 38
382.2 7
Spectrum 1A3.633 min. Scans: 233-235 Channel: Merged Ion: 51 us RIC: 637011BP 91.0 (296123=100%) mhca 7-29-2015 columnei 400 mass.sms
-2-1012345678910111213f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
3.0
0
1.9
6
0.9
7
5.1
4
1.3
172
1.3
347
2.5
529
2.5
735
2.5
917
2.6
123
2.6
512
2.6
682
2.6
900
2.7
070
3.2
488
3.2
663
3.2
862
3.3
037
7.2
152
7.2
176
7.2
328
7.2
361
7.2
597
7.2
898
7.3
059
7.3
075
7.3
105
8.08.59.09.510.010.511.011.512.0f1 (ppm)
10.1
314
PBA 1H-NMR
1.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.5f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
3.0
0
1.9
6
0.9
7
1.3
172
1.3
347
2.5
529
2.5
735
2.5
917
2.6
123
2.6
512
2.6
682
2.6
900
2.7
070
3.2
314
3.2
488
3.2
663
3.2
862
3.3
037
3.3
211
PBA 1H-NMR
7.097.107.117.127.137.147.157.167.177.187.197.207.217.227.237.247.257.267.277.287.297.307.317.327.337.347.357.367.377.387.397.40f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
5.0
0
7.1
949
7.1
984
7.2
072
7.2
152
7.2
176
7.2
328
7.2
361
7.2
597
7.2
853
7.2
898
7.2
951
7.3
059
7.3
075
7.3
105
7.3
225
7.3
266
7.3
289
PBA 1H-NMR
-100102030405060708090100110120130140150160170180190200210220230f1 (ppm)
-2000
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
22000
24000
26000
28000
30000
32000
21.9
4
36.2
4
42.5
5
126.7
9
128.6
5
145.5
0
178.1
1
PBA 13C-NMR
124126128130132134136138140142144146148150152154156158160162164166168170172174176178180182f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
22000
23000
126.6
0
126.7
9
128.6
5
145.5
0
178.1
1PBA 13C-NMR
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
-10000
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
21.9
4
36.1
9
42.6
6
126.5
9
126.7
7
128.6
4
145.4
6
179.0
1
PBA APT
126127128129130131132133134135136137138139140141142143144145146147f1 (ppm)
-10000
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
126.5
9
126.7
7
128.6
4
145.4
6PBA APT
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f2 (ppm)
1
2
3
4
5
6
7
8
f1 (
ppm
)
PBA COSY
1.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
20
30
40
50
60
70
80
90
100
110
120
130
140
f1 (
ppm
)
PBA HSQC
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
200
f1 (
ppm
)
PBA HMBC
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.5f2 (ppm)
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
f1 (
ppm
)
PBA HMBC
Print Date: 18 Sep 2015 13:46:22
MS Data Review Active Chromatogram and Spectrum Plots - 9/18/2015 1:46 PMFile: c:\varianws\data\girlpower\pba 7-29-2015 columnei 400 mass.smsSample: pba Operator: Scan Range: 1 - 759 Time Range: 0.00 - 11.31 min. Date: 7/29/2015 4:01 PM
2.5 5.0 7.5 10.0 minutes
0
100
200
300
400
500
600
kCounts RIC Merged pba 7-29-2015 columnei 400 mass.sms 4000 CENTROID FILTERED 1A
50 100 150 200 250 300 350 400 m/z
0
25
50
75
100
125
kCounts
51.0 7547 65.0
4581
77.0 20459
79.0 36931
80.0 2309
102.1 2942
103.1 18314
105.1 133031
117.1 7877
118.1 37487
131.0 1764
147.0 3641
163.9 19809
165.0 6725 182.9
530 202.0 474
222.1 34
249.1 196
263.0 5
281.1 50
302.0 9
333.2 7
355.0 7
370.8 5
Spectrum 1A3.618 min. Scans: 232-234 Channel: Merged Ion: 86 us RIC: 417810BP 105.1 (133031=100%) pba 7-29-2015 columnei 400 mass.sms
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