Chem806

1
Chem-806

• Other Examples
• COSY and NOESY
• From Dr. Snieckus group

2
Distinguish structures
Rotation around Amide bound 2 isopropyl shifts
3
Distinguish structures
D
d
Me-Ph
Dd
iPr(Me)
iPr(Me)
iPr(CH)
iPr(CH)
CHCl3
CH2Cl2
4
Distinguish structures
a
c
b
b
a
c
CH2Cl2
X
5
Distinguish structures COSY
iPr(Me)
Me
CH
CH2
iPr
CH(iPr)
c
b
b a
a
a
a
CH2
b
c
6
NOESY Phasing (small molecule)
iPr(Me)
Me
CH
CH2
Diagonal in Blue Negative
Cross peak in Blue Negative indicate Chemical
exchange
Cross peak in Black Positive indicate NOE
effect (distance)
exchange
5.03
exchange
3.47
7
Distinguish structures NOESY
CH
a
c/b
CH2
Strong
R-group
c a
weak
8
NOESY slices
a
CH-iPr
c
CH2 weak
CH-iPr
iPr-Me
Me
c
a
b
c
CH
c/b
a
CH2
CH-iPr
CH-iPr
9
NOESY slice Chem. Exchange NOE
iPr-Me
CH
CH-iPr
c
iPr-Me
CH
Me
a
R
CH2
b
c
CH
c/b
a
CH2
CH-iPr
CH-iPr
10
Another example
a
R
b
c
a
c
b
11
COSY
CH3
CH3
CH
CH2
CH2
CH
a
CH2
b
c
R
a
12
NOESY
Diagonal in Blue Negative
Cross peak in Blue Negative Chemical exchange
Cross peak in Black Positive NOE effect
(distance)
Exchange
13
NOESY
CH3
CH3
CH
c
CH2
a
b
CH2
CH
a
CH2
b
c
CH2
R-group
R
c
a
weak
14
NOESY Slices
CH
a
CH2
b
NOE
c
Exchange
Weak CH2
CH3
CH3
CH
CH2
c
a
CH2
b
15
Third example
Me
TMS
Et
?
A/a
TMS
CH3
CH2
16
Third example COSY
Me
Et
A/a?
?
?
C
?
a
B
?
b
?
c
A
bB aA
TMS
?2
?1
17
NOESY to identify
Me
TMS
A
a1
?
Et
a2
?2
?1
C
?
?
a
B
?
a2
?2
b
?
c
A
TMS
TMS side a2 A, ?2 ?
Ethyl side a1 a, ?1 ?
a1
?1
18
COSY Identify aromatic protons
b/c
Et
a
A
C
?
a
B
C
B
?
b
?
c
A
TMS
19
NOESY Identify aromatic protons
Et
C
?
a
Me1
B
?
b
?
c
A
Me2
TMS
Me
b
B
Me1
Me2
20
NOESY to identify stereochemistry
Me
TMS
a
Et
A
?
?
C
?
?
?
a
B
?
b
?
c
A
TMS
Study interaction of CH (? and ?) with aromatic
protons and with CH2
21
NOESY expansion Geometry of CH
Et
C
?
a
B
?
b
?
c
A
TMS
R
a
c
A
a
C