C8953
NMR strukturní analýza
semináˇr
HMBC correlations
Jan Novotný, Ondˇrej Jurˇcek
176003@is.muni.cz, ondrej.jurcek@ceitec.muni.cz
April 11, 2018
Folic Acid: 1H 1D
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
Folic Acid: 13C 1D
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
Folic Acid: 1H-15N HMBC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
300 300
250 250
200 200
150 150
100 100
δ1-15
N(ppm)
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
Folic Acid: 1H-13C HMBC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
150 150
100 100
50 50
δ1-13
C(ppm)
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
Folic Acid: 1H a 13C 1D
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
H23'H23''
H24
H21
H11
H8
H15,17
H14,18
C23
C24
C11
C21C14,18
C13
C15,17
C5
C8,9
C16
C4
C2
C25
C22
C19
C6
Folic Acid: 1H-15N HMBC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
300 300
250 250
200 200
150 150
100 100
δ1-15
N(ppm)
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
N20-H23'
N20-H23''
N20-H21
N12-H21
N12-H14,18N12-H15,17
N7-H8
N10-H8
N7-H11
N10-H11
Folic Acid: 1H-13C HMBC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
150 150
100 100
50 50
δ1-13
C(ppm)
C25-H23'C25-H23''
C25-H24
C22-H23'
C22-H23''
C21-H23'
C21-H23''
C21-H24 C24-H23'
C24-H23''
C24-H24
C23-H23''
C23-H23'
C23-H21
C24-H21
C21-H21
C11-H11
C11-H8
C22-H21
C19-H21
C5-H8
C8-H8
C9-H8
C8-H11
C9-H11
C4-H8
C5-H11
C4-H11
C16-H11
C6-H8 C19-H15,17 C19-H14,18
C16-H15,17
C15,17-H15,17
C13-H14,18
C14,18-H14,18
C14,18-H15,17
N
N
N
N
O
NH2
N
H
O
O
O
–
O
–
O
NH
1
2
3
4
5
6
7
8
9
10 11 12
13
14
15
16
17
18
19
20
21
22
23
2425
Riboflavine: DQF-COSY
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
8 8
7 7
6 6
5 5
4 4
3 3
δ1-1
H(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: 1H-13C HSQC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
120 120
100 100
80 80
60 60
40 40
20 20
δ1-13C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: NOESY
8
8
6
6
4
4
2
2
δ2 - 1H (ppm)
8 8
7 7
6 6
5 5
4 4
3 3
δ1-1
H(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: 1H-13C HMBC
8
8
7
7
6
6
5
5
4
4
3
3
δ2 - 1H (ppm)
150 150
100 100
50 50
δ1-13C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: 1H-13C HMBC + HSQC
8
8
7
7
6
6
5
5
4
4
3
3
δ2 - 1H (ppm)
150 150
100 100
50 50
δ1-13C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: DQF-COSY
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
8 8
7 7
6 6
5 5
4 4
3 3
δ1-1
H(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Me12
H6
H9
Me11
H13''
H13'
H14
H15
H17'
H16, H17''
Riboflavine: NOESY
8
8
6
6
4
4
2
2
δ2 - 1H (ppm)
8 8
7 7
6 6
5 5
4 4
3 3
δ1-1
H(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
H6
H9
H13''
H13'
H14
H14-H13''
H14-H13''
H15-H13'
H15
H16, H17', H17''
H9-H13'' H9-H13'
H9-H14
H11
H12
H9-H12
H6-H11
Riboflavine: 1H-13C HSQC
8
8
6
6
4
4
2
2
δ2 - 1
H (ppm)
120 120
100 100
80 80
60 60
40 40
20 20
δ1-13C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
Riboflavine: 1H-13C HMBC
8
8
7
7
6
6
5
5
4
4
3
3
δ2 - 1H (ppm)
150 150
100 100
50 50
δ1-13
C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
C11-H11
C12-H12
C13-H17''
C17-H17'
C14-H17''C16-H16
C15-H15
C17-H17''
C15-H14
C11-H6
C12-H9
C9-H6
C9-H9
C6-H6C6-H9
H12-C9 H11-C9
H12-C6 H11-C6
H12-C7 H11-C7
H12-C8 H11-C8
C7-H6
C8-H9
C9a-H13'
C5a-H9
C5a-H6
Riboflavine: 1H-13C HMBC + HSQC
8
8
7
7
6
6
5
5
4
4
3
3
δ2 - 1H (ppm)
150 150
100 100
50 50
δ1-13C(ppm)
5a
9a
6
9
7
8
4a
10a
N
5
N
10
NH
3
2
4
N
1
13
14
15
16
17
OH
OH
OH
OH
O
O
CH3
11
CH3
12
C11-H11
C12-H12
C13-H17''
C17-H17'
C14-H17''
C16-H16
C15-H15
C17-H17''
C15-H14
C11-H6
C12-H9
H12-C9 H11-C9
H12-C6 H11-C6
H12-C7 H11-C7
H12-C8 H11-C8
C9a-H13'
C9-H6
C9-H9
C6-H6C6-H9
C7-H6
C8-H9
C5a-H9
C5a-H6
C14-H14
C13-H13'C13-H13''
Next session:
Identification of unknown compound