Molecular Chirality
42
1 Ʉɭɡɶɦɢɧ ȼɢɤɬɨɪ ȿɜɝɟɧɶɟɜɢɱ Ɏɢɡɢɤɨɯɢɦɢɱɟɫɤɢɣ ɢɧɫɬɢɬɭɬ ɢɦ. Ⱥȼ. Ȼɨɝɚɬɫɤɨɝɨ ɇȺɇ ɍɤɪɚɢɧɵ, ɝ. Ɉɞɟɫɫɚ Ʌɟɬɧɹɹ ɲɤɨɥɚ «Ⱦɨɫɬɢɠɟɧɢɹ ɢ ɩɪɢɥɨɠɟɧɢɹ ɫɨɜɪɟɦɟɧɧɨɣ ɢɧɮɨɪɦɚɬɢɤɢ, ɦɚɬɟɦɚɬɢɤɢ ɢ ɮɢɡɢɤɢ» Click here to buy A B B Y Y P D F T r a n s f o r m e r 2 . 0 w w w . A B B Y Y . c o m Click here to buy A B B Y Y P D F T r a n s f o r m e r 2 . 0 w w w . A B B Y Y . c o m
Transcript of Molecular Chirality
1
. . , .
«, »
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
2
The term chiral (pronounced /ka l/) is used to describean object that is non-superposable on its mirror image.
The term chirality is derived from the Greek word for hand, (cheir).It is a mathematical approach to the concept of "handedness"
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
3
“I call any geometrical figure, or group ofpoints, chiral, and say it has chirality, if itsimage in a plane mirror, ideally realized,cannot be brought to coincide with itself."
William Thomson, 1st Baron Kelvin (1824–1907)
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
4Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
5
. « »
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
6
Sn
– Cn, Dn, T, O
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
7
CH
R
NO
H
CH
R
NO
H
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
8Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
9
(-)-
)
C H 3
H
C H 2C H 3
R
(-)-
CH 3
H
CH 2CH 3
O
R
S C H 3
H
H 2 CC H 3
(+)-
S CH 3
H
H 2CCH 3
O
(+)-
)
CH3
CH NH(CH3)
CH OHRS
> (3 )RS
)
S > R (50 )
S P
CH3
O
O NO2H9C4
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
10
X
YV
z
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
11Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
12Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
13Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
14
OH
H CH3
COOH
CH3
» Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
15
S R
T1 = T1’T2 T2’ T3’T3
-1 = 0 2 3<
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
16Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
17Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
18Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
19
.
C BrCl
F {HCFCl} + {HCClBr} + {HCFBr} +
+ {CClFBr} + {HFClBr}
H
!4!4!
NN
C H
BrCl
F
C H
Cl
F
C H
Cl
C H
F
C
Cl
F
H
Cl
F
BrBr BrBr
R SR R R
.1 .3 .4 .5.2
. 1) = 31.8; . 2) = 52.1; . 3) = 37.4;
. 4) = 155.4; . 5) = 144.0;
jij
jijji FDFDk /sch « » -
schF = 1.8
schCl = 1.9
schC = -0.5
schBr = 2.2
schH = -1.7
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
20
Cl Cl
ClHH
H H
H H
H
H H
ClF
Br
HH
(-19.2)
(-19.2)(-19.2)
(9.7)
(-22.6) (-26.8)
(0.0)
(-17.4)
(19.4) (-19.4)
(17.4)
Cl
''
' '
( ---- ---- )
C Br
FH
ClC1
SDM=335
C Br
HH
ClCs
SDM=45
C Cl
HH
ClC2v
SDM=0
Cs
Cl
BrSDM=0 SDM=0
D3
» sch
« » - SDM
SDM 0, C1, Sn, Cnh
Cs, Ci.
Cn, Dn, T, O»
.Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
21
Cl H
F F
ClH
Cl H
F F
Cl
H
Cl H
F
F
H Cl
ClH
FF
ClH
( S R R S R ) ( S R R S R )
( R S S R S ) ( 0 S 0 R 0 )
1
1 1
12
2
2
2
3
3 3
34
4
4
4
5
5 5
5
6
6 6
6
7
77
78
8
8
8
C C FF
H
Cl
H
Cl 12
3456
78
(SC) - – S1 – S5)
S1 = 1,2,3,4 i1S2 = 2,3,4,5 i2S3 = 3,4,5,6 i3S4 = 4,5,6,7 i4S5 = 5,6,7,8 i5
SC = (i1 i2 i3 i4 i5)
ik (R S 0), k = 1- 5, R – « » »S – « »
0 –
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
22Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
23Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
24Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
25Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
26Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
27Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
281D – 3D
Zn Be N ZnBeN
Be Zn N BeZnN
F
Cl Cl
F
ClF FCl
2D
Br F
F Cl
BrF
FCl
Br F
F Cl
BrF
FCl
3D
B
AC
D
A B
C
A B
1D
- - -
(RS/SR)
(RR/SS)
(R 'S'/S 'R ')
(R 'R '/S 'S ')
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
29[4]
OH OH
OH
OH
X2
X3X1
X4
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
30
(EDF)
2D 3D
[4]
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
31
ORRO
OR
OR
X
X
X
X
OHOH
OHOH
XX
X
X
X
X
X
X
OH
OH
OH
OH
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
32Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
33
OH
X X X X
Y Y Y Y
Z1 Z1 Z1 Z1
OH
X X X X
Y Y Y Y
Z1 Z1 Z1 Z1
Z2
OH
X X X X
Y Y Y YZ2
OH
X X X X
Y Y Y Y
Z2
OH
Y
X
Z1
H+
Z2
-Z1
Z1 Z2Z1
NO2 Z2 SCH2COOR
-Z2
**
X = Cl, Br Y = OR , - Ex. = =
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
34
[4]Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
35
– « » (SCi) : SCi = (1/4)FD,FD - .
» » / « » .
»H: -0.08; F: -0.33; C:+0.26; Cl: +0.24; Br: -0.09.
.
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
36
- .
- .
l
l
R
RR
S
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
37– 76
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
38Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
39Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
40Clic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
41
AA
A
B
A AA (A)
BAs
Ar
B
C As
Ar (A)
(A)
C
B A
A
A
A
C
B
E
D A
A
B
C
D
BC B
AA
As Ar
A B C A
« » 1D - 3D
1D 2D 3D
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
42
B
Ar
As
C
Ar
As
B
Ar
As
C
Ar
AsB
Ar
As
C
Ar
As
B
C As
Ar
B
DAr
As
B
C As
Ar
B
DAr
As
B
C As
Ar
B
DAr
As
.
.
.
.
C
Ar
As
B
Ar
As
D
B
As
Ar
B
C As
Ar
.
.D
B
As Ar
B
C
As Ar
.
..
2D
3D
As Ar Bs Br As ArBs Br
1D. .
Click h
ere to
buy
ABB
YY PDF Transformer 2.0
www.ABBYY.comClic
k here
to buy
ABB
YY PDF Transformer 2.0
www.ABBYY.com
![Research on molecular chirality and organic synthesis ...organometallic catalysis Arimasa MATSUMOTO [Chemistry Course] Mechanistic Study of Asymmetric Autocatalysis My research interest](https://static.fdocuments.us/doc/165x107/5ecfb8a1314a29515270e937/research-on-molecular-chirality-and-organic-synthesis-organometallic-catalysis.jpg)
