C8953
NMR structural analysis - seminar
2D NMR spectra, COSY
Jan Novotny
176003@mail.muni.cz
March 20, 2024
1
H-13
C coupled system
58.0 57.8 57.6 57.4 57.2 57.0 56.8 56.6 56.4 56.2 56.0 55.8 55.6 55.4 55.2
ppm
58.0 57.8 57.6 57.4 57.2 57.0 56.8 56.6 56.4 56.2 56.0 55.8 55.6 55.4 55.2
ppm
0
Hz
20406080100120140
O
N
HA
HB
Ph
Problem R-12M. You are asked to interpret the coupled 13
C NMR spectrum of an oxazoline.
(a) Which carbon are we looking at?
(b) Analyze the spectrum, report all coupling constants in the standard format (n
JX-Y = 00.0 Hz).
(c) The spectrum below is of the same compound with one H replaced by D. Where is the deuterium? Place it on
the structure, and explain briefly.
(d) What is the proton NMR frequency of the spectrometer they were using?
HC
HC
2
3
5
6
O
N
Ph
2
3
5
6
15
1
H NMR spectrum of naringenine in d6-acetone
COSY : β-cyclodextrine
5.0
5.0
4.5
4.5
4.0
4.0
3.5
3.5
δ2 - 1
H (ppm)
5.0 5.0
4.5 4.5
4.0 4.0
3.5 3.5
δ1-1
H(ppm)
1D 1
H of Atropine in DMSO
COSY : Atropine
8
8
6
6
4
4
2
2
8 8
6 6
4 4
2 2
δ1-1H(ppm)
COSY : Atropine
5
5
4
4
3
3
2
2
1
1
1
5 5
4 4
3 3
2 2
δ1-1
H(ppm)
Chinin - 1D 1
H
COSY - Chinin
10
10
8
8
6
6
4
4
2
2
δ2 - 1H (ppm)
8 8
6 6
4 4
2 2
δ1-1H(ppm)
5
10
6
9
7
8
3
2
4
N
1
O
CH3
22
11
12
OH
17
16
N
13
15
14
18
19
20
21
COSY - Chinin10 8 6 4 2
8 8
6 6
4 4
2 2
δ1-1H(ppm)
5
10
6
9
7
8
3
2
4
N
1
O
CH3
22
11
12
OH
17
16
N
13
15
14
18
19
20
21
Next topic
1H-1H through space correlations (NOESY, ROESY)