. . , , .
1940 . , w- .
, 50- 20 , .
1953 . .
, , , C-F.
- H,F,O Cl
2.6.1
- | -, Ă | Ă n2 | n1+n2 Ă | 3- (/) | |
H | 2.1 | 1.09 | 1.20 | 2.29 | (99) |
F | 4.0 | 1.39 | 1.35 | 2.74 | (116) |
O(OH) | 3.5 | 1.43 | 1.40 | 2.83 | (85) |
Cl | 3.0 | 1.77 | 1.80 | 3.57 | (81) |
, . , . . , (mimic effect) .
-, C-F , . .
2 pKa .
2.6.2
Ka | pKa | ||
CH3COOH | 4.7 | CH3CH2N+H3 | |
CF3COOH | 0.2 | CF3CH2N+H3 | 5.7 |
CCl3COOH | 0.6 | C6H5CH2CH2N+H3 | 9.6 |
C6H5COOH | 4.2 | C6H5CHFCH2N+H3 | 8.2 |
C6F5COOH | 3.4 | C6H5CF2CH2N+H3 | 6.8 |
C-F . , . , . , , , .
|
|
C-F , . C-F .
, , , .
C-F , , . , , , 5-. , C-F C-H, , , , .
C-F , . , . a- a--a-.
, (suicide enzyme inhibitors).
. , .
pX -R-Ph-O-C2
R | pX | R | pX |
SCF3 | +1.58 | F | +0.13 |
OCF3 | +1.21 | NO2 | +0.11 |
CF3 | +1.07 | H | |
SOCF3 | +0.93 | COOH | -0.15 |
Cl | +0.76 | OH | -0.49 |
CH3 | +0.51 | NHCOCH3 | -0.79 |
, .
, , , . .
, , , . , -, , .
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