'.

.
E-mail:bezvold@ukr.net .
. ,
,
. , y = a + b/x + c/x
' '.
- '.
' ' ',
.
: , , ,
, ', '.
.
' .
, '. ' . '
'. ,
6, 10 .. ( 4n + 2) , 4, 8 .. .
', ,
, . ', -
.
'
, ( ',
', ). , ' - ,

' (A A, A B). ',

', , .
1

 ' , - '
1,5 ',
. ,
. '.
.
, (),
( 1 2):

.... .....
.... ...
H

_+ C _ +
_
H
+
C
_C
_+
+
_
+
C
C
_
_
H
H + +C _+

.. ..
..

6
5+

+1

+ -

_2

4_

_ -

+3

, ( 2).
. 2.
1 2 6 ( 2) (1 (+),
2 (-), 6 (-)), 1 2 6. ,
1 6 1 2 1,210 ,
1,397 120.
1 6 1 2 , [1]:

.. ..
..

6
H3C CH3

H2 C

CH2

HC

Lc _ c = 1,543

Lc = c = 1,338

CH

LC

= 1,205

5+

+1

1,210

4_

_2

+3

L 1 _ 2 = 1,210

, 1 2 1 6 , 1 (+) 2 (-) 1 (+) 6 (-) . .

,
1 2 6 ( 3):

.. ..
..

6
a

a+b
b

5+

+1

+3

.. ..
..

6
_2

5+

.. ..
..

6_

+1

_2

+3

+1

2,420

5+

+3

L1 _ 2 = L 1_ 6 = 1,210
L1 _ 4 = 2,420

4, ( 4)
, , ,
1 , 1 (+) 4 (-)
.
6 (-) 3 (+), 2 (-) 5 (+). 1 4
2,420 . , , 1 2,
1 6 (1,210 2 = 2,420 ).
, , . ,
,
, , 1,5.
, - ,
.
3

 - 1 (+) 4 (-), 2 (-) 5 (+), 3 (+) 6 (-)

5:

.
.
.. ..

6
5+

.
.
.. ..
_

+1

+3

5
sp - .
:

= 3/2 = 1,5

8 (3 + 3 + 2 = 8). ,

. , :

.
.
... ...
.. . ..
...
_

, , ,
, , ,
4

 . , ,
',
, '.
, , , [2], [3].

2_

1,3,5,7- [4], [ 5].
- ' 1,41 .
CH3
CH3

2_

L c-c ~
~ 1,41

H3C
CH3

: , (15) , ,
' . ,
.
[2, .79].
(- [10]-).
+
. ._
.
+.
_.
.+
.
+ . . ._
_

n = 10

+
.
.
._
+.
_.
.+
.
+ . . ._
_

. . .C
B

4,309

ABC = 144 oC
Lc-c = AB = BC = 1,400

n = 10

'
, . , (4,309
L- = 1,400 ), (24)
.
80.
- - , ,
[2, .84], [6].
,
( ), .
.
Lc-c = 1,397

Lc-c = 1,410

6_

8_

5+

.. ..
..

+1

_2

+3

.. . ..
...
+1

7+

+5

_2
+3

_4

.. . . ..
.. . .

Lc-c = 1,400
+1 _ 2
10 _
+3
_

9+
_
8

7+

+5

L1 _ 2 = L 6 _ 1 = 1,210

L1 _ 2 = L 8 _ 1 = 1,303

L1 _ 2 = L10 _ 1 = 1,331

L1 _ 4 = 2,420

L1 _ 5 = 3,404

L1 _ 6 = 4,309

, 1 2 1,210 ,
1,303 , 1,331 ( ).
(0, 15, 24)
, (2,420 ;
3,404 ; 4,309 ), 1 2 (1,210 ;
6

1,303 ; 1,331 ),
. () .
,
( 1,210 2,420 ).
.
. .
,
Lc-c = 1,400 L(1-5) = 3,380 , L(1-2) = L(8-1) = 1,293 ,

L- = 1,410 .

, [18]-, ( ).
. ,
= f(L) = f(L), , L
, / y = a + b/x + c/x
- (C-C, C-N, C-O, C-S, N-N, N-O, O-O, C-P).
, , .
[1]:
H3C

CH3

Lc_ c = 1,543

H2 C

CH2

HC

Lc = c = 1,338

LC

CH
C

= 1,205

- , 1, 2, 3.
[1, c.116]:
H 3C

CH3

- =347,9397 /

H2 C

CH 2

HC

CH

= 615,489 / = 812,278 /

( . ) - ,
,
.
.
:
cc ' = 0,06040343

5,67787529 11,28562201

2
L
L

(1)

 ' = 2221,34518418

5065,62912191 1699,18638789

L
L2

(2)

:
cc (L = 1,397 ) = 1,658
cc (L = 1,42 ) = 1,538 1,54
Ecc (L = 1,397 ) = 534,0723 /
Ecc (L = 1,42 ) = 503,3161 /
, , ,
.

.... .....
.... ...
_

HC
+
HC

H
C

CH
_

+ -

CH

C
H

.. ..
..
_

_ -

,
1,5, :
1,5 = 0,06040343

5,67787529 11,28562201

2
L
L

(3)

L = 1,42757236 .
, 1,5,
cc L = 1,42757236 .
1,5,
L = 1,42757236 :
L = 1,42757236 = 2221,34518418

5065,62912191 1699,18638789

2
1,42757236
1,42757236

Ec c (L = 1,42757236 ) = 493,3097 /

1,658

Ecc = 534,0723 /, :
E = 534,0723 / 493,3097 / = 40,7626 /.
40,7626 / - , - . ,
:
E1 = 40,7626 / 2 = 81,5252 / (19,472 /).
8

,
, :
E = 3E1 = 3 81,5252 / = 244,5756 / (58,416 /).

.. . .
..
_

..
.. . .
_

.. ..
..
_

_ 3 E = 244,5756 /

(, - ' ).
- :
E2 = 3Ecc + 3Ecc = 2890,286 /
cc 1,658 :
E3 = 6 534,0723 / = 3204,434 /
, :
E = E3 E2 = 3204,434 / 2890,286 / = 314,148 /
(75,033 /).

.
.
= f(L) E = f(L) - ',
, L , /.

3_
_
2
_
1

, /

..
.

..
.

L,

L,

' , .
[1]:

H3C

CH3

H2 C

Lc_ c = 1,543

CH2

HC

Lc = c = 1,338

LC

CH
C

= 1,205

- , 1, 2, 3.
[1, c.116]:
H 3C

H2 C

CH3

- =347,9397 /

CH 2

HC

CH

= 615,489 / = 812,278 /

y = ax + b, ,
b :

a=

b=

xy x y /n

x 2 x /n

(4)

y /na x / n

(5)

n .
, ,
r2 =

[ xy x y / n ]

(6)

[ x x /n ] [ y y /n]
2

r2 , .
, = f(L) = f(L)
y = a + b/x + c/x2 , -
.
y = a + b/x + c/x2 , X = 1/x,
Y=

y y1
1/ x1 / x 1

, b1 = b + c / x 1 ,

: Y = b1 + X,

,
c=

1/ xY 1/ x Y / n

(7)

1/ x 1/ x /n
2

10

b1 =

Y / nc 1 / x /n

(8)

n Y.
a : y = na + b(1/x) + c(1/x2),

(9)

n = 3.
= f(L) CC, C=C, CC.
1. = f(L).
1/x

1/x

y y 1

1/ x y y 1

1 / x1/ x 1

1/ x1/ x 1

x (L, )

y ()

0,74738416 0,55858308
0,82987552 0,68869338

10,07089756
11,00186391

7,52682927
9,13017751

1,543
1,338
1,205

1
2
3

1,57725967 1,24727645

21,07276147

16,65700678

4,086

1/x1 = 0,64808814

x1 = 1,543

y1 = 1

(1/x2) = 1,66729469

(1/x) = 2,22534781

c = 11,28562201

b = - 5,67787529

, = 0,06040343

n = 3
a = - 0,06040343

5,67787529 11,28562201

L
L2

(1)

:
CC () = 1. = () = 2. () = 3.
CC () (L = 1,42 ) = 1,538 1,54.
CC () (L = 1,397 ) = 1,658
, - 1,658,
1,667 [2, .48].
, y = a + b/x + c/x
(1, 1), (2, 2) (3, 3 ) , b, ,
() .
. ,
y = a + b/x + c/x = f(L) E = f(L)
. , = f(L) '
(Lcc = 1,397 , = 1,667) r = 0,9923
= -0,55031721, b = -4,31859233, = 10,35465915.
= f(L) E = f(L) '
11

 ', , b, ,
( , ').
'.
= f(L) CC
y = a + b/x + c/x

X = 1/x

Y=

b1 = b + c/x1

Y = b1 + cX

y y 1
1/ x1/ x 1

:
c=

b1 =

1/ xY 1/ x Y / n

(7)

1/ x 1/ x / n
2

Y / nc 1 / x /n

(8)

n Y.
: y = na + b(1/x) + c(1/x2),

(9)

n = 3
2. E = f(L).
1/x

1/x

y y 1

1/ x y y 1

1 / x1/ x 1

1/ x1/ x 1

x (L, )

y (E, /)

0,74738416 0,55858308 2694,46159281 2013,79790195

0,82987552 0,68869338 2554,29339132 2119,74555296

1,543
1,338
1,205

347,9397
615,4890
812,2780

1,57725967 1,24727645 5248,75498413 4133,54345491

4,086

1775,7067

1/x1 = 0,64808814
(1/x2) = 1,66729469
c = - 1699,18638789

x1 = 1,543

y1 = 347,9397

(1/x) = 2,22534781

n = 3

b = 5065,62912191

' = 2221,34518418

a = - 2221,34518418

5065,62912191 1699,18638789

2
L
L

:
Ecc () = 347,9397 / = () = 615,4890 /
() = 812,2780 /

12

(2)

 , , .
()
,
PAO = 60

QPO =

O
A

AF = 1,397

OA = AF
AFE = 120

PQO = 60
PQ = OP = AF

. sin 60

PQ = OP = AF . 3 = 1,397 . 3 = 1,210
2
2
PQ = 1,210
PR = 2PO = 2 . 1,210 = 2,420

D
135o

.
K

.O

.. . .
B
A

BAO = 67,5o
tg BAO =

OC = AC . tg BAO =

AB . tg BAO
2

o
CD = 2 . OC = tg BAO . Lc-c = tg 67,5 . 1,410 = 3,404

OC
AC

AC = CB, Lc-c = AB = 1,410

OK = OC,

CD
= KO = OC = 1,702
2

:
KC 2 = KO 2 + OC 2 - 2 . KO . OC . cos COK

COK = 45 o

KC = 1,303

Lc-c = AB = 1,400 :
Lc-c = AB = 1,400
CD = tg 67,5o . 1,400 = 3,380
CD = KO = OC = 1,690
2
2
KC = KO 2 + OC 2 - 2 . KO . OC . cos COK

COK = 45 o

KC = 1,293

13

D
144o

BAO = 72 o

.O

. . . . .B
K
A C

tg BAO =

AC = CB, Lc-c = AB = 1,400

OC
AC

AB
OC = AC . tg BAO = 2 . tg BAO

CD = 2 . OC = tg BAO . Lc-c = tg 72o . 1,400 = 4,309

OK = OC, CD = OC = KO = 2,154
2

:
KC 2 = KO 2 + OC 2 - 2 . KO . OC . cos COK

COK = 36 o

KC = 1,331

.
, ' ,
, '. ' . ', ' ,
'.
, . , , .
( ):
1)
().

AA

AB

2) , ,
, .
.
3) .
4) , . 5 2.
14

5) ( ) ,
() .
6) - .
, ' , -, ,
.
'.

. .+ _. .+ _
.
+.
._ .+ _. .+
_

. .+ _. .+ _
.
+.
._ .+ _. .+
_

. .+ _. .+ _. .+ _
.
+.
.
_. . _ .+ .
_ .
+
+
_

. .+ _. .+ _. .+
._
+.
_. . _. .+ .
_ .
+
+
_

. .+
. ._
_
. .+ _.+ ._+
.
+.
._ .+ _. .+
_

15

. .+ _
. .
_
_+
+
. . . ._ +
.
+.
_. . _. .+
+
_

. _. +. ._
_.
_
+.
. .+ _ .+._
_.
. .
.+_ + _. .+ ._. +
..
.+
.
.
.
_
_
+
+
+

. ._ +. ._
_.
.+._
_
+.
+.
.
+.
_.
._ . +
. _. . + ._
+_
..
.+
.
.
.
_
_
+
+
+

H
H
H
H
H

H
H

H
H
H
H

H
H

. .+ _. .+ _
.
. .+
_ .+
.+ _. HH H HH . . _
H
_+
.
+.
_ .
_. . .
+
+
_

. .+ _. .+ _
.
. .+
_ .+
H
.+ . HH HH . ._
_
H
_+
.
.
+
_ .
_. . .
+
+
_

[18]-
, ,
[18]-, .
[18]- '. , ,
,
. (12 )
( ), (6 ) ( ). [7]. , , . .
, ( ).

16

, , ()
, ,
.
.

. ._
_ .
.+ N ._. +

. ._
_.
.+ N ._. +

. ._
_.
.+
N . ._N
+

_
.
.
_.
.+
N . ._ N
+

_
.
.
_.
.
.+ N._N +

_
.
.
_.
.
.+ N._N+

. .
_.
.+ N ._. +

. .
. .+
. ._
+ N

. .
. .+
N . ._N
+

_
+ N

_
+ N

. .
_.
.+
N . ._ N
+

+ N _

_
+ N

N
N

1,3,5-

17

. .+ _. .+ _
.
+.
.
_
_. . .
N +
+
_

. .+ _. .+ _
.
+.
.
.
_. . _ N +
+
_

. .+ _. .+ _
.
+.
N
_. . _. .
+
+
_

. .+ _. .+ _
.
+.
N
_. . _. .
+
+
_

. .+ _. .+
+.
.+ ._
.
_. . _ N
+
_

..N

. .+ _. .+
+.
. ._
_ N
_. . .
+
_

. .+ _. N .+
N
+.
._ N .+ ._ .+N ._
_

N
N

.N.

+ _. N +
.
.
.
N
.
._
+
.
_. . ._ N
N +
_

_
.
.+
+.
_. +. .
_
X

. .
.
+
+
+
_. . ._
X
_

..X
X = O, S, NH

, ,

18

_
.
N
.+
+.
_. +. .
_
X

. N.
+
+.
+
_. . ._
X
_

..X
X = O, S, NH

, ,

_
.
.+
+.
N
_. +. ._
N

. .
.
+
+
N
_. +
. ._
N
_

..N

_
.
.+
+.
_. +. ._N
N

. .+
+.
+ ._N
_. .
N
_

..N

1,2,4-

_
.
N
.+
+.
N
_. +. ._
N

. N.
.
+
+
N
_. +
. ._
N
_

..N
H

N
N

1,2,3-

19

_
.
.+
+.
_. +. ._
CH

CH

O
R

R
O

. ...
.
...
.. .
..O.

_+ O _
+
C_
+_ +

O
R

N
+

O
_

.. ..
.
.
.
N _.
.
+ _. .+
.O..
_ + O_
+

O
C6H5

O
_
O

..O...
.. ...
S... .O
.. . .
.O..
_

_+

C 6 H5

+_ +

+_
+

20

.....
.
.... .

.X..
R

..NH

_
_+ X
+
C_
+
+_ NH

R
2

X = O, S

..X ..

..

..

H 2N C NH 2

. ... ..
.. .
.
H N. . . C . . .
2

_ X
+
_
+ _ _+ _ _ +
+ NH
+

X = O, S

..

H 2N

.NH
. _
+
_.
+
.
. _ _ +. . ._ .+ NH
H N . .+ . C +
_

NH2

..

C NH2

..
.
O
CHO
.. .
.
C.. .CH ...C
.
.
OC H
...O..

C2H5 O

CH

C
OC2H5

O
Na

_+

+ +

_+

Na

21

O
CH3 C

.....
.. .
...

CH

+_O
+
_ _ _
CH3 C + + CH

COOC 2H 5

Na

COOC 2H 5
Na

H2C

CH

H2 C

CH2

. . . CH ._ +. ._ CH
+_ +

...O..._ _+...O..
+
.+._N+.. _
.. _+
.O..._.+

...O..._ _+...O..
+
.+._C+.. _
.._
.O..._+.+

..O...
..
...O.....S........O...
..O.

2 _

...O ..O..

.. O+. _.. .+._ ._. O+. ..

+ +

22

+
_
+

+_

.O. + _
.
....O_..+. . ._..+O....
+

_+

+
_

..N+. ._..+.._ O+...

..N. ..O..

NO

.+

NO 2

...O
.

...O...

. ._
.
N
.+._ .+
_+.
+. .
.O.. ..O.
_

NO 2

..

.N..+_
.
..+ ._
_ +.
+. .
..O.. ..O..

..O.. ...O...

. .. . .. . .. .
.
.
. . .. .. . .. ..
. . . . . . .. . . . . . . . . .
. .. .. . . .. . .. . . .. .
..... . .... ... . ..
. .. .. . .

+
_

+
_

+
_

_+

+
_

+
_

+
_

+
_

+
_

, '
, ,
( ) ().
,
, .
, (
23

 ) '. '
(2,420 ). ,

,
3,35 ( - '
1,42 ) [8]. '
.
2,420 ( ), ,
.
, ( ,
) , ,
,
( ).

.
E = a + b/L + c/L2 = a + b/L + c/L2
',
'.
3 4 a, b, c
' (C-C, C-O, C-N, C-S, N-N, N-O, O-O).
- '.
' ( ') ,
.
.

. ' (
' E = a + b/L + c/L2 ) '
. (N-H '
):

24

..
HN

.+..O..
_.
+
.
.
_ _ +. _ + _ +
+.
H N. .
C . . . NH
_

O
C

.NH
.

LC-N = 1,33 , LC-O = 1,27 (8)

-N = 1

-N (L=1,33 ) = 1,686

- = 2

- (L=1,27 ) = 1,486

EC-N = 291,834 / [1, .116]

C-N (L = 1,33 ) = 523,790 /

EC-O = 728,538 / ( R2C=O) [1, .116]

EC-O (L = 1,27 ) = 496,940/

E1 = EC-O + 2EC-N = 1312,206 /

E2 = EC-O + 2C-N = 1544,520 /

E = E2 - E1 = 1544,520 / - 1312,206 / = 232,314 /

, ( ')
232,314 / (55,487 /).
.
, ': ,
' ' .
' 1,5,
' (, ),
'
, ' ( ). ,
' .
, '
. , '
.
'
8, 9 ( ,
(3,5) (3) (2,5)).
',
, ,
' ( ) .
25

 , , a, b, c 3 4
= f(L) E = f(L).
3. = a + b/L + c/L '.
'

C-C

-0,06040343

-5,67787529

11,28562201

C-O

26,03252883

-72,46498138

52,43899244

C-N

0,63817306

-7,56455294

11,91384503

C-S

55,33256579

-198,81807222

181,87538814

N-N

0,96407492

-6,68791795

9,79339013

N-O

46,00756377

-123,75637485

84,79763896

O-O

23,89786759

-66,85172754

48,79304255

C-P

28,76548555

-109,46128312

107,52805439

- ',
L - ' .
4. E = a + b/L + c/L '.
'

C-C

-2221,34518418

5065,62912191

-1699,18638789

C-O

11420,81052442

-31359,17576343

22207,04265404

C-N

-2332,69568587

4450,61712191

-866,48412671

C-S

-27772,64385690

90244,55278987

-71414,57485742

N-N

7067,14065437

-20274,81508318

14878,53765631

N-O

-6564,31416262

15895,54907490

-8769,11638979

O-O

10590,40848780

-29935,02909385

21430,93279023

E - ' /,
L - ' .
.
1. . . , , 1973 , .143
( Structure and mechanism in organic chemistry. Second Edition, INGOLD C.
K., Cornell University press Ithaca and London, 1969).
2. . . , . 4- . ,
, 1987 , 1, .84 ( Advanced organic chemistry. Reactions,
Mechanisms, and Structure. Third edition. Jerry March, Professor of Chemistry Adelphi University.
New York, 1985).
3. T.J.Kats, Journal of the American Society. 82, 3784, (1960).
26

4. ., . . 2- . ,
, 1981 , 1, .335 ( Advanced Organic Chemistry. Francis A.
Carey and Richard J. Sundberg, University of Virginia, Charlottes, Virginia. Plenum Press, New
York, 1977).
5. J.F.M.Oth, G.Anthoine, J.M.Gilles, Tetrahedron Lett. 6265, (1968).
6. S. Masamune, K. Hojo, Kiyoti Hojo, G. Bigam, D. L. Rabenstein, Journal of the American
Society. 93, 4966, (1971).
7. . . . 2- . , , 1981 , 1,
.583 ( Contemporary organic chemistry. Second edition. Andrew L. Ternay.
University of Texas, Arlington, 1979).
8. . . , , 1988 , .3, .17-18
( Structural inorganic chemictry, fifth Edition, Wells A. F. Clarendon Press,
Oxford, 1986).

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