( )N+1 -

( CH 3)CH 2

()NMR
. NMR
.

.
.

F ,12H ,136C ,147N ,178 O,11H

19
9

16
12
NMR .

8 O, 6 C

I2 I .
1

I

I

31

Si

29

19

17

13

11

Isotope

1/2

1/2

1/2

5/2

1/2

3/2

1/2

)Spin (I

)NO (I

. ( )

.
()+2/1 ()-2/1
( . )1

( . )2

( . )3

B0

1
2

1
2

. 3

Eabsorb ( E 1 E 1 ) h
2

. B
)
0

) E f ( B0

 .
. ( )

E f ( B0 ) h

:

h / 2

h
) B0 h
2

( E

( ) B0
2

 ()
.

.
.

( ) .

.
.

Nu
e E / kT e h / kT
N0

60MHz 298K
1,000,009
1,000,000 :

Nu
1,000,000
0 / 999991
N0
1,000,009

, .
RF . ,
, .

H
()MHz

20

40

60

80

12

100

16

200

32

300

48

600

96

.

. .
.
.
.

) B B0 (1

.
.

.

. .

( .
CH 3 )TMS
4 Si

Hz NMR ppm

Hz
MHz

- 1 (: )CW .

-2 :
.

. .

. ( )FID .


, .
. ,
, . ,
.
H

H
H

H
H

H
H

H
H

(CH3 ) 4 Si

CH3

H3C

, NMR .
, ,
( . .
)

) :
. ,
. .

-CH2-CH2-CH2Br

H signal

1.25 1.69 3.30

/ ppm

. ,
.

(CH3)4Si

CH4

CH3I

CH3Br

CH3Cl

CH3OH

CH3F

Compound, CH3X

Si

Br

Cl

1.8

2.1

2.5

2.8

3.1

3.5

4.0

Electronegativity of X

0.23

2.16

2.68

3.05

3.4

4.26

Chemical shift, / ppm

) : ,

.
sp 3

(
sp 3

C CH
CHC
3 ,
) C , C CH C2

0
,

H
H

R
H

Cycle
0

R
R

10

H
R

20
1

30
2

sp 2

)C HC

sp (
1S
, C H s

. , s sp 3 1
5
6 .

sp 3 .
7 8

33
.%

2
3
sp
% H

sp ,

)
25

.7/ 5 4

sp

32

) 1s, C H
(sp

.
.

sp

) (
2 .
sp

sp 2

( ) ( ) ,

.
10 12 .
O

O
H

H
O

.
:
( )
.

( )

R
R

. .
) ( ) .
.
(
, .

RCOOH

10 / 5 12 / 0

ArOH

4/0-7/0

ROH

0/5-5/0

RNH 2

0/5-5/0

RCONH 2
-CH=CH-OH

5/0-8/0

15

.
.
( )

,

. . ( )
.

:
NMR

. .
.

 ( )N+1

( )n ( )
( )n+1 .

.
A B .
B

1
)Y .
2

Cb
R

1
2

1
2

( ) x B

Ca

Cb

Ca

1
2

A B .

A B .

X Y A
. A B

A
Y
( - B
) .

A
B

B
X
( - B
) .

 ( ) CH 3CH 2

( )A

1 / 83

1 / 83

3 / 2 .

3/ 2

( . )B

n+1 .

.
.


( )J . ( )cps
( )Hz .
.

.
.

 .
. .



13

)
) 13-



NMR 13-


: 13-

( )NMR
. NMR

. NMR ( )FT-NMR
.

 13-

12- NMR . 13-

) ( I

2

C 13

1
C 600013 .
H

13- 1/08
.

13

C

.

13

13

1
4

 13-

13- .
.

.
TMS (

) . (

).

608
ppm
.

40
(
70.)ppm

) 100 150 ppm.

155 220 ppm

C
1 H
13

.C

13

13

CNMR

sp

2

. .

* C-13 Chemical Shift Ranges

. C
13
13

C
.
.
- .
Para
2 / 9 ppm

Meta
0 /1

Ortho

Ipso

0/7

9/3

CH 3

C1 Base Ipso Meta 128 / 5 9 / 3 (0 / 1) 137 / 7 ppm

CH3

C2 Base Ortho Ortho 128 / 5 0 / 7 0 / 7 129 / 9 ppm

C3 C1
C4 Base Ortho Para 128 / 5 0 / 7 (2 / 9) 126 / 3 ppm
C5 Base Meta Meta 128 / 5 2 (0 / 1) 128 / 3 ppm
C6 C 4

CH3

13

C
- 13-

C
- .
C
13
13

n+1 . .
13

CNMR
. . NMR .

13- J
250-100 Hz .

13-
.

n2
n 1 3

n 1
n 1 2

n0
n 1 1

18.46

80

70

60

50

40
PPM

30

13.13

H3C

10

49.24

77.27
76.43

77.08

38.71

19.95

44.85

28.05

25.70

n3
n 1 4

CH3
11

CH3

2 9
6
7

1 1a
5

OH
8

200

150

100
ppm

50

20

10

13C

13

CNMR


.
.
- .
13
.

C

.

13
C

. (
) NOE . .
.

CH3

e
c,d

c,d
b

a
CH3

d
c

e
d
c

b
a

e
a

CNMR

CNMR
. .
a

Cl
Cl

Cl

a
c

Cl

c Cl

Cl

 NMR 13-

FT-NMR

.

.

13
.

CNMR

CDCl
(
)
3 ( d

(CD3
SO ) CD3

CD3 CO CD3

13C

CHD 2
(

1
(
(

= )1 . .

) 1

( 2n I

i i

: I 1
2
i

i
1
= 0
.

2
.

 19
31-

19- 31-
1
2

. .



:
)
)
)

...

:
....

: ...

( )J ( )
.
NMR .

.
.

.
:

J (13C 1H ) 156 Hz

13- (C-
)H 156 Hz . H-C-
. C-H

J (1H 1H ) 8 Hz

.
.

J 13
13

J CH
J .

HH

.
.
.
( ) ( ) (
) .

( )

( )

3 1
)
(...., J , J

.
) (...., 4 J , 2 J

) (

.
.
( )J .
J .

J .
13

C . 19
F

.
H
13sC :
1
J

sp n

1
)
n 1

()J CH (500Hz

) ( )J

NMR .
.
2 J .
~50 Hz

H
C
19F

-9to -15 Hz

0 to 2 Hz

H
~5 Hz

H
C
H

13C

H
H

H
7-14 Hz

H
C
31P

~ 2 Hz
D
~160 Hz

( )HCH ( ) .

19F
19F

. J2
) ( HCH
.

40

(J HCH )
( ) HCH

30
20
10

130 0

120 0

110 0

100 0

90 0

J HH

2 J .

CCC ( p ) HCH ( s

) .
.
J HH
H
C
H

-9 to -15 Hz

-13

H
-11

-9

-4

H
X
-2

H
+2

HCH

 ) ( ) J

C-H C-
H .
3J

H-C-C-H .
3.
J



)C
( H
.
C
. H


.

C
H
H

.
CH
CH .

CC CH

C-H .
180 0

BH ,H A

.
.

0

90

C 0 0
H

.
C
H
90 0

1800

3
.

J HH
. :

J HH A B cos C cos 2
C 5

B 1

A7

)
: (
4
J n
J
.

.
.

COOH
H

O
H3C

CH3

O
H
CH3

HOOC

H
H3C

CH3
H

H
H3C

NMR .
.


.
:
)1
.
( J)
)2
.
:

NMR .

- .

 :
n+1

n+1
.
n+1 .
. .
( )
n+1

Hc
C

Ha
C
Hb

A B
J AC J BC

J AB 0

()

Ha Hc
C C
Hb

A B
J AC J BC
J AB 0

1 H .
H A , H
.


B

(b)
H
H
(a)

(c)
H
O

(d)

3.83
Hc

3.12
Hb

2.77
Ha

ab

Jab

bc

Jac

bc

ac

J ab 5.8 Hz
J bc 4.1Hz
J ac 2.5 Hz

NMR
3
sp ( )

n+1 .

.
Hc , Hb , Ha
c

J ab 3J ac 3J bc

Hb

H H H

Ha

Hc

.
Hb
Ha

J 0 5Hz

Ha

Ha

Hb

Hb

J 11 18 Hz

J 6 15 Hz

cinnamic acid

vinyl acetate

.
H

H
H

3 J CH
120
0
. HCH

.
:
C Hb

Ha

J~ 0-3 Hz

Ha
C Hb
4

J~0-3 Hz

.
) ( 4 J
.
C-H

4 C-H C=C
.

HzJ 0
4
.

J 3Hz

CH2SO2
3

Cl

Cl

H3C

H3C

NMR
( )-CH-OH .

- :
. .
NMR
.

R O Ha R/ O Hb R O Hb R/ O Ha

5
10

.

10 3
10 2
.

.
.
CH
.
J
2

CH2OH

CH3
2

JCH CH
3

OH
2

J CH CH
3

CH2OH

CH 3 CH 2 OH

 D2 O

) / /

OH NMR

OH . )1( : ( )2
( )3 1:1
CH 3

OH
)
(

CH 3COOH

()

CH 3

OH

OH

()

)
.
OD2
0 .
.
.
.

RCOOH D2O RCOOD DOH

ArOH D2O ArOD DOH

ROD DOH

ROH D2O

RNH 2 D2O RND2 DOH

.

1
HNMR
DOH .
DOH
DOH .

 D2 O
NMR .
2 D2 O 2 Na 2 NaOD D 2
RCOOH NaOD RCOONa DOH

NaOH
/ D2 O
.

RCH 2 COR 2 NaOD RCD2 COR 2 NaOH

NaOH D2 O NaOD DOH

O
2 DClD . DOH .
RNH 2 3DCl RND3 Cl 2 HCl
HCl D2 O DCl DOH

)
.
NMR
NMR .
nmr

(
. .

CDCl
NMR

)
3

- .


)
. (

.
pH
1

R CH 2 NH 2 H R CH 2 NH 3
)( pH 1

.
H
N

H
C
3

J ~7 Hz
HH

H
N C H
H H

O
R C

phenethylamine

butylamine

NH2
H C Me

CH3CH2CH2CH2NH2

. (

1
I
)
2

-1 0 +1 .

.
.
. _
NH-CH HO-CH _ N-H
.

1
.
I
2

1 I
2

NMR .

. .
( ) I=0 .

. (

.
1
I
.
2

:
)1 . . ( ) N-H
( ) -1 0 +1 .
)2 . .
( )N-H () .
.
)3 .
.
NMR NH 9/0 ppm 7/0
.

pyrrole

:
)1
)2
)3 ( ) NH

.

N,N-dimethylformamide

NMR

.
G G . G
G .

A
C

'G
x

C
C

2-methyl-2-butanol

H NMR

2-methyl-2-butanol C NMR

 :
200 MHz 300

1969
.
() .
:
(- ) -8887766(--22- -)53-
.
CH3

CH3

CF2CF2CF3

CH3

+3

Eu

CH
C

CH3

CH
C

CH3
C

C
CH3

CH3

Eu(dpm)3

+3

Eu

CH3

CH3
Eu(fod)3

)
)

)
:

)
)
)
)
)
)
)

.

( ) 400-800 nm
( ) 1 mm .

 ( )
.
cm1
. ( )
.
)c(cm / sec
) (cm

*c

1
(cm )
) (cm
1

400-4000 nm

. H 2 ,Cl2
.

.
.
( )C=C
( ) HC CH .
CH3

CH3

CH2

H2C

H3C

H3C

CH3

H3C
C
CH3

C
H3C

CH3

C
H3C

.
.

.

.
O
H

C-H

.
. (
)

.

H
C

H
C

H
C

H
C
H

C
H

Symmetrical-stretchink

Asymmetrical-stretchink

Wagging

Rocking

Twisting

Scissoring


:
-CH -CH- : - NH -NO
.
C=O .
,
NH , (R
) NH .
. N=O .
( )

H
H
H

H
H
H

C
O

C
O

H
N

N+

N+
O

 , .
, .

( ) .

( 2 )1

, .

.
)
( = 1 - 2
,
.
.

, ,
.

(E h )

2 ( ) K ( m
) m .
:

m1m2

m1 m2

k .

.
:
k
,

.

2150

1650

1200

,
:

C-I

C-Br

C-Cl

500

550

800

CH

C-O

C-C

C-H

1100

1200

3000

k
.
CH()3000
CH ()1340

 ,
sp sp 2 sp 3 CH :
C

2900

3100

3300

( )K .
C=O cm 1715 ,
1675-1680 .
c=o
. K
.
O

O
C
C

:
()

()FT

4000cm 400
.

 ()



. (
) .
( )FT

. FT-IR
. .
.

. FT-IR
.

( ) .

4000 400 .
:

.
: .
( KBr
)

( )CCl

C ,C=C, C=N ,NO

C= O ,O-H , N-H, C-O , C
.

.

.1

1660-1820 .
.

.2

C=O (
3 ) .

OH
( 2400-3400 C-H ).

NH
3400 .

C-O
. 1000-1300

C=O 1810 1760 .

CH
2850 2750 . CH

.3 C=O :

OH .

3300-3400
C-O 1000-1300 .

NH .
.3400
( C-O )OH 1000-1300 .

 .4 /
C=C 1650 .
1450-1650
.

C-H
3000 ( C-H
).

 .5
C=N . 2250
C=C . 2150
C-H 3300 .

.6

1530-1600 . 1300-1390
.7
.
3000 .
1450 1375 .

:
:
C-H
CH
CH
CH

()3000
()1465
()1375
( ) 4 5 CH
( 720 )

C-C

( )

=C-H
=C-H
C=C

( )3000
( )OOP 650-1000
1600-1660

: -2 -1

3300
2150

-1


( C-H )

C-H .
2750-3300 .
3000
.
C=C
:
C=C 1640 1670
. C=C .
:

1640
:
-11 1650 :
1670 :
: ( )1670 ()1658

.
:

( )
.

90
.
60 .
C=C
C-C .

C-C C=C ( )
C=C .
(90 )120 C-C
C=C ( . )

 :
1566

1656

1611

1650

1646

a
H
C

C
C

120

1611
H
C
C

90

 C=C

1883

1788 R

1656

1641

1675

1566

R
R

1679

1650

1611

1681

1675

1646

( ) .
p C-C
. p
s .
.
1655

1651

1656

1678

CH2

CH2

CH2
CH2

1780

1940

CH2
CH2

H2C

 C-H
C-H -1000
650 . .

( ):
990
910 .

-21 :
700 970 .

-11 ( ) :
890

 :
815

:
.


=C-H
=C-H
C=C

3000
( 690-900 )
1600 1475 .
/ 1667-2000

: , , ,

 C-H

690 ( 750)

750

690

780

880

800-850

O-H

3600-3650
3300-3400

C-O

( 1000-1260 )

: -2 , , ,

 ) (O-H

O-H
( ) .
: C-O
C-O 1000-1260 .
C-O C-X
( )
.

 C-O O-H

(3)
(2)
(1)

C-O
1220
1150
1100
1050

O-H
3610
3620
3630
3640

C-O .

C-O

( 1000-1300 C=OOH

: ,


C-O-C 1000-1300 .
R
)H(R
R

O
C

O
R

CHR

HCR

CH

H2C

Ar

(1120)
: c-o-c
1250 ( 1040)

 c-o-c
:
R

1120

C
H

H2C

CH

H2C

1220

:
1230-1280 815 -950
. 750-880

1020-1200



1650-1850 .
C=O :

1690
1810

1710

)1

1715

1725

1735

1760

( )2

1800

c=o .
c=o .

c=o
( ) .
c=o
c=o .


c=o .
.

.


c=o
.
.

1760 .
.
c=o
1710 .
O
R

C
O

 c=o :

c=c
c=o c=c .
c=o
.
.
O

C
C

.
c=o .
.

c=o 30 .
O

O
O

NH

1705

1690

1770

1735

1780

1715

1745

1715

( )
.
c=o
. ( )
.
O
C

:
.
O

Cl

Cl

c=o
. .
OCH3
C
O
H
O

C=O
C-H

1725

2850

, ,

2750

c=o .
C-H
.

1715

C=O
C

( ) 1100-1300

, ,

O-H

( ) 2400-3400

C=O
C-O

1700 -1730

1210-1320

, , ,

C=O
C-O

1735-1750

1000- 1300

, ( ) , ( ) ,
, ( )


( )

C=O 25 -15
.

CH3
OCH3

C
O

1726

OCH3

C
O

1725

H2C

CH3CH2CH2COCH2CH3
O

1738


C=O ( ) .
O

O
CH2

CH2

C
C

C
C

C=O

OCH3
C
O
H
O


C=O ( )
.

1770

1735

C=O
N-H
N-H

1630-1680
( ) NH 3350 3180
1550-1640

-N

C=O -1680
1630 .
() , C=O
.

C=O
C-Cl

1775 -1810

550 -730

C=O
C-O

:
1800 -1830 1740 -1775
900-1300

1800-1830 1740-1775
.
.

N-H

N-H
N-H
C-N
:

.3300-3500
.



1560-1640
1500
800
1000-1350
, , -N , -3 ,

 R-C=N

-C=N

2250

, ,

R-N=C=O
-N=C=O

2270

R-N=C=S

-N=C=S

2125

 R2C=N-R

-C=N-

1640 -1690

1530-1600

() 1300-1390

N+
O

() 1490-1550
1315-1355

O
C

( ) 1600
() 1400

N-H
N-H

() 2600-3300
() 1500-1610
( ) : 1610 .1500
1550-1610
.


O
O

O
CH

OH

NH3

CH

NH2

.
:

, ,

:

.
.

.

.
.

.


.

.

.
.
.

. :
1 2
mv eV
2
m v e V
. .

 :
mv
eH

r H .
:
m H 2r 2

e
2V

.

. :
M
R
M

 R M M M
.

.

.
.

.

.

. .

.

.
.

e
.

.

.

.


6
10

.
.


.

m
. e
.
(m ) 2 .

m1
*

m*

m1 m2

m m1 m2
.

.
.

.
.

.1
.

.
. 2 .
.3

.

.

 :
> > >
> > > >
> > > > >

:
(
m
) e
.


.

( )45 .

(C2 H 5 NH 2

, :
, 30 .
m 30 .
e

13

31 . 13C %1.08 12 .
%2.16 , . 1.08*2=%2.16
M+1 :

)( M 1
M

* %(M 1) 100

m
e

 M+2

* .2

)2

* (.016

200

)2

* ( M 2) (1.1
* %( M 2) 100

M
200

BrCl:
%M+2=(98*1)+(32.5*1)=130.5

(100 *1) 2 (32 .5 *1) 2

%M 4

27 .64
400
400

Br2Cl Br3 , Cl3 , Cl2 Br

.
.

.
105
.


.
.

.

.

.

.

 . ,
,
.
,
.

.

:
C6H5CH2

< < R2CH < R3C < CH2CHCH2

CH3 < RCH2

.
.

.

.

Cn H 2n Cn H 2n 1 .

.

.

 m/e=41 .
. :

CH2

C
H

CH2

CH2

C
H

CH

R +

CH2

C
H

CH2

.

.
.

 -
. :

-1 ,

, -2

-1

.
( )m/e=39 .
CH2

CH2

R + H

CH2

M-1 .

H + C

-1

 -1



.


( )m/e=91 .
m/e=91 .


.
.

CH2

CH2

CH2

CH2

C
CH3

CH2

CH

CH3
H

H H

:
R1

R1
OH

R +

C
R2

OH

R2

.
.
.

 .
.
21- .
. 41
:
(CH2)n

( CH2)n

+ H2O

CHR

CHR

RCH

RCH
HO

:
H
O
R

CH2

+ H2O + CH2

CH

CH2

H2C
H2C

CHR
CH2

:
O

OH

+H

OH

OH
H

OH

H
C
H

(2)

OH
C

H
CH3

CH2

C
H
C

CH2
H

(3)

+ C3H7

OH

+ H2O

 .
:

OH
CH2OH

+ H2

C6H5

m/e = 77

m/e = 79
+ CO

m/e = 107
+ H

 28
m/e .
M-28
m/e m/e . ( )HCO.
M-29 .

 - 2

.

:
.1 :
+ H

CHO

+ R

CHO

: .2
R

CH2

R +

CHO

H2C

CH

: .3

R
CH

CH
R

CH2

CH

C
R

H2C

CH

0H

.
.
: (.
)

:
R

H
C
CH2

H
CHR

+
CH2

CH2

C
R

C
CH2

: ) (
O

O
H

CH2

+ C2H4

H
CH2

CH2CH2CH2 + CO
O

H
CH2

+ C3H7

CH3

CH2

O
H

C
CH3

+ CH3

R
CH

CH2

C
CH2

OH

H
C

C
CH2

+
CH2

 -2

.
.

RCO .

CH3OC =O

= 59

m
e

 .
:

H
C

CH

+
CH2

CH2

OH

H3CO

CH2

C
C
H2

H3CO

.
OH COOH
C=O .

.
m
e = 60 .
R

H
C

OH

H
CH

HO

CH2
CH2

CH2

C
C
H2

60

HO

.
.
.
:

NH2

+ CH2

m/e=30

 .
:

CH + CH2CH2CH2

H3C
N

m/e=42

+ H
CH3

CH3

m/e=84

CH2
CH2 + CH3

m/e = 42

H2C

CH2

H2C

m/e=85

H2C
N

CH3

m/e = 57

N
CH3

 .
:
H

+ HCN

+ H

m/e = 66

+H

m/e = 65

NH2

NH

m/e = 92

m/e = 93

 ( )
, .

CH2

C
R

CH2
N
H

CH2

CH2

CH

m/e = 93

 -3

 -N

.
.
m

=44
e

. - :
O
NH2

m/e = 44

R +

NH2

R
H
H

OH
C

+
CH2

H2C

m/e = 59

CH

H2N

CH2
CH2

H2N

 -N

.

RCH = C = N .

H
C
H2C

NH

C
CH2

m/e = 41

HC
CH2

C
H2C

, ,

.

.
m
= 30
e
NO2 me =46
.
.
NO , NO2 m/e = 30,46 .
,
.

 , :
O
NO2

+ NO

m/e = 93

m/e = 65

NO2
CH

HC

C4H3 +

m/e = 51

+ NO2

m/e = 77

.


34 .
.

.

:
.

.

.
.
.

+ HX

C
H

CH2

CH2

CH2

:
X

R + H2C

H2
C

CH2

+ R
H2C

CH2
C
H2

CH2

H2C

CH2
C
H2

 -1 -2-