Identification of unknown compound
Ondřej Jurček
April 26, 2017
Ondřej Jurček
April 26, 2017        1 /7
Task 0: Classification of an unknown substance
Assign the general name to displayed
substances:
CARBOHYDRATE PEPTIDE STEROID TERPENE ALKALOID COUMARINE
April 26, 2017       2 /7
Task 0: Classification of an unknown substance
lJLJuLüi
a    J AVUft A    -       A aIa,
1
I
Task 1: Ci0Hi3NO
5[ppm]        Multiplicity Integral 1.05              triplet 3 1.75             singlet 3 3.70             quartet 2
7-7.60 complex multiplet 5
Ondřej Jurček
April 26, 2017       4 /7
Task 2: CnHi5N02
5[ppm]    Multiplicity   -/(Hz) Integral
1.30	triplet	7	3
3.00	singlet	-	6
4.25	quartet	7	2
6.65	dublet	8	2
7.80	dublet	8	2
April 26, 2017       5 /7
Task 3: Ci2Hi7N02 - ^/COSY
!H NMR (300 MHz, CDCI3)
cn o [-01   01   01 m
4 a   n   u> h
01    H    00    lO    CM O
d   n   H  H m
11 ji 11111III ji III11II111IIIIII11111IIIII11 ji III11111 ji 7.7    7.5    7.3    7.1 ppm
in oi
in  "i 01
co • in in (M
•     I (n
«    ) I
H0\00[^VDin(nH00lí)f0H0>cno
u>inmmmininin(nm(nmoio\<n
H    H    O O
| 111 1111 111 1111 11 11111 11 11111 11 11111 11 1111 111 1111 11 11111
I11 11111 11 1111 111l|lI111 1111 11 1111
2.6   2.4   2.2   2.0   1.8   1.6   1.4   1.2 ppm
r
I
JLJLLJ
X
i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i—i
8 7
0.92 1.08
1.84 1.00
2
ppm
2.08 2.05 2.91
2.94 2.02
Ondřej Jurček
April 26, 2017       6 /7
Task 3: Ci2Hi7N02 - ^/COSY
COSY (300 MHz, CDCI3)
Jdu.
JUl
Ondřej Jurček
P2
(ppm):
1-
8
April 26, 2017       6 /7
Task 3: Ci2Hi7N02 - 13C/HSQC,HMBC
HSQC (300 MHz, CDCI3)
tmít w**jkMiil*Ětk}^ě
WM|I ^
Ondřej Jurček
F2
(ppm)
1-
m—i i i i
i i i i—i i i i
I  I I I--MM
Mil--MM
MM--Mil
MM--II II
Mil--II II
II  II--MM
140 120 100 80 60
Fl (ppm)
40
20
April 26, 2017       7 /7
Task 3: Ci2Hi7N02 - 13C/HSQC,HMBC
HMBC (300 MHz, CDCI3)
F2
(ppm)~ 1
2
3
O o
6
I   I    I   I    |    1   I    I    I I    III   |    I    I   I   1 I    I    I    I    [   I    I    I   I I    I    I    I    |    I   I    I    I        I    I    I   I    |   I    I   I    I        I   I    1    I   |    I   I    I   I I   I   I    1    |   I    I    I   I        1    I    I   I    |    I   I    I    I        I    1    I   I   |    I    I   I    I        I   I    I    I   |   I    I    I I
180        160        140        120        100 80 60 40 20
Ondřej Jurček
April 26, 2017       7 /7
Relative stereochemistry on a ring: NOESY
Provide the full assignment of1H resonances and determine the
orientation of H5 and H6.
NOESY
A.
rrr
4.Z
—I— 4.0
—I— 3.8
—I— IE
			0			
o			0			
						
						
O 0		* <		0	<o i	3
@ ©		it				
	■	>				
		© 0	o 0	V		
						
-3 2
-3.4
—I— 3.4
—I—
3.2