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STRUCTURE OF THE BENZENE MOLECULE

ON THE BASIS OF THE THREE-ELECTRON BOND.



Bezverkhniy Volodymyr Dmytrovych.
Ukraine, E-mail: bezvold@ukr.net
Abstract: Using the concet o! three-electron bond one can reresent the actual electron
structure o! benzene, e"lain seci!icity o! the aromatic bond and calculate the
delocalization energy. #t $as sho$n, that !unctional relation y % a & b'" & c'"
(
!ully
describes deendence o! energy and multilicity o! chemical bond on bond distance. #n
this article carbon-to-carbon bonds are revie$ed. Using these deendences it is ossible to
calculate chemical bound energy by di!!erent bond distance or di!!erent multilicity o!
chemical bond, that makes ossible to calculate delocalization energy o! benzene
molecule.
Keywors: three-electron bond, interaction through the cycle, sin, delocalization energy,
bond energy, bond multilicity.
INTRODUCTION
)hemical bond has been al$ays a basis o! chemistry. *dvancement o! chemical science
can be considered as evolution, develoment o! concets about chemical bond. *romatic
bond is !undamental basis o! organic chemistry. )oncet o! three-electron bond in benzene
molecule enable to e"lain seci!icity o! aromatic bond. #t also becomes aarent, $hy
lanar molecules $ith +, ,- etc. electrons .according to /0ckel rule 1n & (2 must be
aromatic, and lanar molecules $ith 1, 3 etc. electrons cannot be aromatic by de!inition.
,
Descrition o! chemical bond, that is given by 4uantum theory, esecially in terms o!
method o! molecular orbitals, is 5ust a mathematical model. 6his model is an aro"imate
reresentation o! molecules and its bonds, $hereas 4uantum-mechanical calculations o!
organic molecules re4uire considerable simli!ications and are e"tremely comlicated.
)oncet o! three-electron bond and develoed mathematical relations in this $ork are
rather simle, illustrative and give e"act results o! di!!erent values .bond multilicity,
chemical bound energy, delocalization energy o! benzene2. 7ne must clearly imagine, that
three-electron bond is 5oint interaction o! three electrons $ith relative sins, that results in
898 898
ne$ tye o! chemical bond .* : : : *, * : : : B2. 6his bond tye, three-electron bond,
makes ossible to describe real molecules o! organic and inorganic comounds $ithout
invoking virtual structures, $hich do not e"ist in real terms.
Using o! three-electron bond be!ore descrition o! benzene molecule enables to
determine delocalization energy o! benzene in an elementary $ay, understand $hy
multilicity o! ;-; bond o! benzene is more than ,.< and to understand the main oint o!
aromatic bond in general, $hich is aeared to be rather illustrative. Besides, !or
determination o! delocalization energy it is not re4uired to select re!erence structures.
Delocalization energy !ollo$s !rom the concet o! aromaticity o! benzene and its structure
on the basis o! three-electron bond.
RESULTS AND DISCUSSION
=uosing that the chemical bond bet$een t$o atoms can be established by means o!
three electrons $ith oositely oriented sins .8982 the structure o! the benzene molecule
can be e"ressed as !ollo$s .see !igure , and !igure (2:
(
#t is interesting to oint out that sins o! central electrons on oosite sides have an
oosite orientation .see !igure (2. >o$ let us consider in detail the interaction o! si"
central electrons bet$een themselves. 6hey $ill be itemized as sho$n in !igure (. *s the
sin o! electron , and those o! electrons ( and + are oositely oriented .see !igure (2
., .&2, ( .-2, + .-22, electron , $ill be attracted to electrons ( and + resectively. ?et@s
indicate that the distance bet$een electrons , and + or , and ( is e4ual to ,.(,- A $hich
can be easily sho$n taking into account the distance bet$een atoms o! carbon in benzene
to be ,.BCD A and the angle bet$een carbon atoms amount to ,(- degrees. ?et us
comare the distance bet$een electrons , and + and , and ( bond lengths in ethane,
ethylene and acetylene E,F:
*s $e observe, the distance bet$een central electrons , and ( and , and + o! the
benzene molecule is aro"imately e4ual to that bet$een carbon atoms in the acetylene
B
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&
&
&
&
&
&
&
&
&
G
G
G
G
G
G
G
G
G
)
)
)
)
)
)
/
/
/
/
/
/
.
.
. .
.
&
&
&
G
G
G
,
(
B
1
<
+
!igure ,
!igure (
G
&
H H
H H - u$ard sin
- do$n$ard sin
) /
B
)/
B
) / )/ ) /
(
)/
(
) )
?
% ,.<1B A ?c%c
% ,.BB3 A
% ,.(-< A
?c
G
c
.
.
.
.
.
&
&
&
G
G
G
,
(
B 1
<
+
?
,
G
(
% ,.(,- A
. ,.(,- A
molecule, there!ore, the interaction bet$een electrons , .&2 and ( .-2 and , .&2 and + .-2
has to be rather considerable. ?et us e"ress the attraction $ith arro$s. *ccording to
summing u vectors the resultant vector $ill be directed to the centre, $hich means that
electron , under the in!luence o! electrons ( and + $ill move to the centre .!igure B2:
#! $e take a look at electron 1 $e see the similar situation $ith it .!igure 12 and it $ill
also move to the centre and, more imortantly, its sin and that o! electron , $ill be
oositely oriented, i.e. electron , .&2 and electron 1 .-2 $ill be attracted through the
cycle. Electrons + .-2 and B .&2 and electrons ( .-2 and < .&2 $ill interact similarly. 6he
distance bet$een electrons , and 1 in benzene is e4ual to (.1(- A. #t is interesting, that
this distance is t$ice as much than distance bet$een electrons , and (, or bet$een
electrons , and + .,.(,- A I ( % (.1(- A2. 6his interaction through the cycle constitutes
the essence o! the delocalization o! electrons, o! course together $ith a three-electron
bond. =ince besides the three-electron bond in the benzene molecule there is an interaction
through the cycle, meaning that the benzene nucleus undergoes a kind o! comression it is
clear that the c-c bond multilicity in benzene $ill e"ceed ,.<.
=o, the aromatic system is a cyclic system $ith three-electron bonds $here an
interaction o! central electrons through the cycle is observed. #n the benzene molecule
there are three interactions through the cycle-air$ise bet$een electrons , .&2 and 1 .-2,
1
a
b
a & b
.
.
.
.
.
.
.
&
&
&
G
G
G
,
(
B 1
<
+
.
.
.
.
&
&
&
G
G
G
,
(
B 1
<
+
.
.
.
.
&
&
&
G
G
G
.
.
.
(.1(- A
?
,
G
(
% ,.(,- A
?
,
G
% (.1(- A
1
,
(
1
B
<
+
?
, +
G
%
!igure B !igure 1
( .-2 and < .&2, B .&2 and + .-2, as sho$n in !igure <:
)arbon atoms in benzene are sJ-hybridized. 6he three-electron bond bet$een carbon
atoms in the benzene molecule can be reresented as !ollo$s:
)arbon atoms in benzene have an octet e4ual to 3 .B & B & ( % 32. #t should be ointed
out that due to the largest distance !rom the atoms nuclei the central electrons o! the three-
electron bond are suosed to be the most mobile comared to other electrons o! the three-
electron bond. 6he interaction o! central electrons $ith oosite sins through the cycle
can easily e"lain $hy cyclobutadiene and cyclooctatetraene are not aromatic comounds:
<
. .
.
. .
.
. .
.
. .
.
&
& &
&
&
&
G
G
G
G
G
G
,
(
B 1
<
+
!igure <
& &
&
&
G
G
G
G
.
. .
.
.
.
.
.
.
&
&
&
G
G G
G
.
.
.
.
.
.
&
.
)
)
multilicity % B'( % ,.<
*s $e see both in cyclobutadiene and cyclooctatetraene, electrons interacting through
the cycle have the same sins and, clearly, $ill be reulsed, there!ore there $ill be no
interaction through the cycle and the molecule $ill not be aromatic. #n cyclobutadiene at
the e"ense o! small distance it causes the aearance o! antiaromatic roerties, and in
cyclooctatetraene there is a ossibility o! !ormation o! non-lanar molecule, $here
interaction o! central electrons becomes imossible and molecule losing the interaction
through the cycle loses also three-electron bonds, that results in a structure, in $hich
single and double bonds alternate.
E"lanation, that cyclooctatetraene is non-aromatic, because it is non-lanar and does
not hold $ater, insomuch as dianion o! cyclooctatetraene is aromatic and has lanar
structure E(F, EBF.
Klanar
L-ray crystal structure analysis determined crystal structure o! otassium salt o!
dianion ,,B,<,D-tetramethylcyclooctatetraene E1F, E<F.
7ctatomic cycle is lanar $ith lengths o! ;-; bonds nearly ,.1, A.
Klanar
Mrom the mentioned above $e can make a conclusion: cyclooctatetraene con!orms to the
+
(
_
)/
B
)/
B
)/
B
) /
B
(
_
?
c-c
N
N
,.1,
A
shae o! bath tub not because o! high angular ressure .,<O2 at lanar structure, but
because by interaction through the cycle central electrons o! three-electron bonds have
e4ual sin and $ill ush a$ay. 6hus !or energy reduction cyclooctatetraene con!orms to
the shae o! bath tub and becomes non-lanar, that disables interaction o! central
electrons.
)yclobutadiene reresents rectangular high reactivity diene E(, .DCF.
#t is also interesting to observe cyclodecaentaene .cis-isomer E,-F-annulene2.
Phereas central electrons o! three-electron bonds have oosite sins, then interaction
through the cycle is ossible. But distances bet$een central electrons on oosite sides,
$hich interact through the cycle, are e"tremely long .1.B-C A i! accet ?Q-Q % ,.1-- A !or
regular decagon2, angular ressure is high .(1O2 and that@s $hy stabilization at the e"ense
o! interaction through the cycle at such long distance $ill be lo$ and cannot cover energy
consumtion !or creation o! lanar molecule.
D
&
G
.
&
G
.
.
.
.
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.
.
&
&
&
G
G
G
&
G
.
&
G
.
.
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.
.
&
&
&
G
G
G
n % ,-
.
.
.
1.B-C A
*
B
)
n % ,-
*B) % ,11
?c-c % *B % B) % ,.1-- A
o
)
)yclodecaentaene $as received in the !orm o! crystalline substance at - 3-O;. 7n
sectrums RS;->TU and RV->TU it $as determined, that comound is non-lanar and is
ole!in, that is logical on the basis o! long distance bet$een central electrons E(, .31F, E+F.
?ets dra$ our attention to the !act that in going !rom benzene to cyclooctatetraene and to
cyclodecaentaene distance increases not only bet$een central electrons on the oosite
sides .interaction through the cycle2, but also bet$een neighboring central electrons. ?ets
sho$ it on !igure.
*s $e can see distance bet$een neighboring central electrons , and ( in benzene makes
u ,.(,- A, in regular octagon ,.B-B A, and in regular decagon ,.BB, A .almost as
distance bet$een carbon atoms in ethene molecule2. 6hat is by going !rom benzene to
regular octagon and decagon not only angular ressure .-O, ,<O, (1O2 and distance bet$een
central electrons increase, $hich are situated on the oosite sides .(.1(- AW B.1-1 AW
1.B-C A2, as $ell as distance bet$een neighboring central electrons , and ( .,.(,- AW
,.B-B AW ,.BB, A2, that causes considerable $eakening o! interaction through the cycle in
regular decagon. 6hat@s $hy regular he"agon .benzene2 is ideal aromatic system. *s
angular ressure is e4ual to zero, distances bet$een central electrons both neighboring and
situated on the oosite sides are minimal .accordingly ,.(,- A and (.1(- A2. #.e.
3
.
.
.
.
&
&
&
G
G
G
. .
?
,
G
( % ,.(,- A
?
,
G
% (.1(- A
1
,
(
1
B
<
+
?
,
G
%
.
.
.
.
.
. .
.
&
&
&
&
G
G
G
G
,
(
B
1
<
+
D
3
?
,
G
( % ,.B-B A
?
,
G
% B.1-1 A
?
,
%
3
G
<
.
.
.
.
.
.
.
.
.
.
&
&
&
&
&
G
G
G
G
G
,
(
B
1
<
+ D
3
,-
?
,
G
( % ,.BB, A
?
,
G
% 1.B-C A
?
,
%
G
?c-c % ,.BCD A ?c-c % ,.1,- A
?c-c % ,.1-- A
+
+
,-
interaction through the cycle $ill be ma"imal. By going to regular decagon these
advantages $ill be lost. 6hat@s $hy cyclodecaentaene is ole!in.
?et us note !or comarison that i! $e take ?c-c % ,.1-- A !or the lanar cyclooctatetraen,
$e $ill have ?.,-<2 % B.B3- A, ?.,-(2 % ?.3-,2 % ,.(CB A $hich vary 5ust slightly !rom
the above mentioned distances bet$een the central electrons at ?Q-Q % ,.1,- A.
By means o! the interacti on through the cycle together $ith the three-electron bond,
three aromaticity o! coronen, E,3F-annulene, nahthalene and other organis substances can
be e"lained .see conclusion2.
>o$ let@s ass to the de!inition o! delocalization energy o! benzene. #t is easy to sho$,
that relation multilicity % !.?2 and X % !.?2, $here multilicity is multilicity o! bond,
? Y length o! bond in A, X Y energy o! bond in k5'mole $ill be described by !unction
y % a & b'" & c'"J !or any tyes o! bond .)-), )->, )-7, )-=, >->, >-7, 7-7, )-K2.
Pe shall consider ethane, ethylene and acetylene to be initial oints !or the c-c bond.
Mor lengths o! bonds let us take the date E,F:
*s usual, the ;-; bond multilicity in ethane, ethylene and acetylene is taken !or ,, (, B.
Mor energies o! bonds let us take the date E,, .,,+F:
6he given bond energies .according to ?. Kauling2 are bond energy constants e"ressing
the energy that $ould be sent !or an ideal ruture o! these bonds $ithout any !urther
rebuilding o! the resulting !ragments. 6hat is, the above mentioned energies are not bond
dissociation energies.
C
) /
B
)/
B
) / )/ ) /
(
)/
(
) )
?
% ,.<1B A ?c
%
c
% ,.BB3 A
% ,.(-< A
?c
G
c
) /
B
)/
B
) / )/ ) /
(
)/
(
) ) E
% B1D.CBCD k5'mole
% +,<.13C k5'mole
% 3,(.(D3 k5'mole
) ) E ) ) E
/aving er!ormed all necessary calculations $e obtain the e4uation:

cc bond multilicity % -. -+-1-B1B
<.+DD3D<(C
L

,,. (3<+((-,
L
(
.,2

X o! QQ bonds % (((,.B1<,31,3
<-+<. +(C,(,C,
L

,+CC. ,3+B3D3C
L
(
.(2
Mrom these e4uations $e !ind:
cYc benzene multilicity .? % ,.BCD A2 % ,.+<3
cYc grahite multilicity .? % ,.1( A2 % ,.<B3 Z ,.<1
EcYc benzene .? % ,.BCD A2 % <B1.-D(B k5'mole
EcYc grahite .? % ,.1( A2 % <-B.B,+, k5'mole
Being a$are that the benzene has the three-electron bonds and also the interaction
through the cycle, $e can calculate the interaction through the cycle energy.
Mor this urose $e have to determine the energy o! the [clean\ three-electron bond, that
is o! the bond $ith a ,.< multilicity and to do that $e shall solve the e4uation:

,. < % -. -+-1-B1B
<.+DD3D<(C
L

,,. (3<+((-,
L
(
.B2
!rom the e4uation $e !ind ? % ,.1(D<D(B+ A.
=o, i! the benzene molecule had a [clean\ three-electron bond $ith a ,.< multilicity the
c-c bond length $ould be ? % ,.1(D<D(B+ A.
,-
.
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.
. .
.
.
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.
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.
.
&
&
&
G
G
G
)
)
)
)
)
)
.
.
. .
.
&
&
&
G
G
G
G
&
H H
H H /
/
/
/
/
/
- the sin directed u
- the sin directed do$n
>o$ let us determine the energy o! the [clean\ three-electron bond $ith a ,.<
multilicity kno$ing its length ? % ,.1(D<D(B+ A:
XQQ ? % ,. 1(D<D(B+ A % (((,. B1<,31,3
<-+<. +(C,(,C,
,. 1(D<D(B+

,+CC. ,3+B3D3C
,. 1(D<D(B+
(
Ec Y c .? %,.1(D<D(B+ A2 % 1CB.B-CD k5'mole
6aking into account that the benzene c-c bond energy $ith a ,.+<3 multilicity is e4ual to
Ec-c benzene % <B1.-D(B k5'mole, the di!!erence $ill make:
]E % <B1.-D(B k5'mole Y 1CB.B-CD k5'mole % 1-.D+(+ k5'mole.
1-.D+(+ k5'mole is the energu o! interaction through the cycle er one c-c bond. 6here!ore,
the energy o! interaction through the cycle $ill be t$o times higher:
E
,
% 1-.D+(+ k5'mole I ( % 3,.<(<( k5'mole .,C.1D( kcal'mole2
#t is clear that the three interactions through the cycle resent recisely the $orking
benzene delocalization energy $hich is:
E % BE
,
% B I 3,.<(<( k5'mole % (11.<D<+ k5'mole .<3.1,+ kcal'mole2
#t is also ossible to calculate the benzene molecule energy gain in comarison $ith the
curved cyclohe"atriene .let us assume that energy o! )-/ bonds in these molecules is
similar2. Mor this $e calculate the sum o! energies o! single and double c-c bonds in
cyclohe"atriene:
E
(
% BEcYc & BEc^c % (3C-.(3+ k5'mole
,,
.
.
.
.
.
.
.
&
&
&
G
G
G
.
.
.
.
&
&
&
G
G
G
.
.
.
.
&
&
&
G
G
G
.
.
.
B
.
E % (11.<D<+ k5'mole
E
E
E
6he energy o! si" benzene c-c bonds $ith a ,.+<3 multilicity is e4ual to:
E
B
% + _ <B1.-D(B k5'mole % B(-1.1B1 k5'mole
6here!ore, the gain energy o! benzene comared to cyclohe"atriene $ill amount to:
E % E
B
Y E
(
% B(-1.1B1 k5'mole Y (3C-.(3+ k5'mole % B,1.,13 k5'mole
.D<.-BB kcal'mole2

E!"ERIMENTAL
?et@s sho$ more detailed calculation o! ratios !or our mathematical relations. ?et@s
consider relation Tultilicity % !.?2 and E % !.?2 !or ;-; bonds, $here multilicity is
multilicity o! bond, ? Y length o! bond in A, X Y energy o! bond in k5'mole.
*s initial oints !or the given bonds $e $ill use ethane, ethene and acetylene.
Mor the length o! bonds let us take the !indings E,F:
*s usual, the ;-; bond multilicity in ethane, ethylene and acetylene is taken !or ,, (, B.
Mor the energy o! bonds let us take the !indings E,, .,,+F:
,(
) /
B
)/
B
) / )/ ) /
(
)/
(
) )
?
% ,.<1B A ?c
%
c
% ,.BB3 A
% ,.(-< A
?c
G
c
G
G
G
the multilicity
.
.
.
.
.
.
,
(
B
?, A
E, k5'mole
?, A
) /
B
)/
B
) / )/ ) /
(
)/
(
) ) E
% B1D.CBCD k5'mole
% +,<.13C k5'mole
% 3,(.(D3 k5'mole
) ) E ) ) E
#! $e have t$o variants and $e received the set o! oints and $e marked them on the
lane in the rectangular system o! coordinates and i! the resent oints describe the line
e4uation y % a" & b that !or choose the coe!!icients a and b $ith the least medium-
4uadratic de!lection !rom the e"erimental oints, it is needed to calculate the coe!!icients
a and b by the !ormulas:

a =

xy
x

y / n

x
(

x
(
/ n
.12

b =

/ na

/ n
.<2
n-the number o! given values " or y.
#! $e $ant to kno$ ho$ big is the derivative, it is necessary to state the value o!
agreement bet$een calculated and evaluated values y characterized by the 4uantity:

r
(
%
[
xy

/ n
]
(
[
x
(

x
(
/ n
] [
y
(

y
(
/ n
]
.+2
6he ro"imity o! r
(
to one means that our linear regression coordinates $ell $ith
e"erimental oints.
?et us !ind by the method o! selection the !unction y % a & b'" & c'"
(
describing the
deendence multilicity % !.?2 and E % !.?2 in best $ay, in general this !unction describes
this deendence !or any chemical bonds.
?et us make some trans!ormations !or the !unction y % a & b'" & c'"
(
, $e accet
L % ,'",
` %

yy
,

,/ x,/ x
,

, b
,
% b & c/ x
,
,
than $eall receive: ` % b
,
& cL, that is the simle line
e4uality, than
,B
c =

,/ xY
,/ x

Y / n

,/ x
(

,/ x
(
/ n
.D2
b
,
%

Y

/ nc

,/ x

/ n .32
nYthe number o! given value `.
?et us !ind a !rom the e4uality: by % na & bb.,'"2 & cb.,'"
(
2, .C2
$hen n % B.
?et us !ind no$ multilicity % !.?2 !or )c), )^), )d).
6able ,. )alculation o! ratios !or relation Tultilicity % !.?2.
,'" ,'"J

yy
,

,/ x,/ x
,


,/ x

yy
,

,/ x,/ x
,

" .?, A2 y .multilicity2


-.D1DB31,+
-.3(C3D<<(
-.<<3<3B-3
-.+33+CBB3
,-.-D-3CD<+
,,.--,3+BC,
D.<(+3(C(D
C.,B-,DD<,
,.<1B
,.BB3
,.(-<
,
(
B
b ,.<DD(<C+D ,.(1D(D+1< (,.-D(D+,1D ,+.+<D--+D3 1.-3+ +
,'"
,
% -.+13-33,1 "
,
% ,.<1B y
,
% ,
e.,'"
(
2 % ,.++D(C1+C e.,'"2 % (.((<B1D3, $hen n % B
c % ,,.(3<+((-, b % - <.+DD3D<(C a % - -.-+-1-B1B
6here!ore the multilicity o! cc bonds % -.-+-1-B1B
<. +DD3D<(C
L

,,. (3<+((-,
L
(
,

?et us !ind !rom the e4uation:
Tultilicity )f) .ethane2 % ,. Tultilicity )^) .ethylene2 % (.
Tultilicity )d) .acetylene2 % B.
Tultilicity )f) .grahite2 .? % ,.1( A2 % ,.<B3 Z ,.<1.
,1
Tultilicity )f) .benzene2 .? % ,.BCD A2 % ,.+<3
*s $e can see the multilicity )f) o! benzene bond is ,.+<3 it is near the bond order o!
,.++D calculated by the method T7 E(, .13F.
#t should be noted that the g, b, Q coe!!icients !or this y % a & b'" & c'"J !unction in case o!
using three airs o! oints .h
,
, i
,
2, .h
(,
i
(
2 j .h
B,
i
B
2 are de!ined e"licitlyW actually, they .the
coe!!icients2 are assigned to these oints. #n that $ay $e !ind these coe!!icients !or $orking
!urther $ith the e4uation. Mor making certain that this deendence y % a & b'" & c'"J
describes $ell the Tultilicity % !.?2 and E % !.?2 !unctions it $ill take only to er!orm
correlation !or !our or more oints. Mor e"amle, !or the deendence Tultilicity % !.?2 !or
)-) bonds $e should add a !ourth oint .?cYc % ,.BCD A, Tultilicity % ,.++D2 and obtain
an e4uation $ith rJ % -.CC(B and the coe!!icients g % --.<<-B,D(,, b % -1.B,3<C(BB,
Q % ,-.B<1+<C,<. *s it is di!!icult, due to ob5ective reason, to de!ine !our or more oints !or
the Tultilicity % !.?2 and E % !.?2 e4uations !or a searate bond tye, $e $ill !ind the g,
b, Q coe!!icients using three oints .as a rule they are the data !or single, double and trile
bonds2. 6he deendences obtained in such a $ay give good results as regards the bond
multilicity and energies.
Pe@ll !ind the deendence E % !.?2 !or the )f) bonds

y % a & b'" & c'"J L % ,'" ` %

yy
,

,/ x,/ x
,

b
,
% b & c'"
,
` % b
,
& cL
*s usual:
c =

,/ xY
,/ x

Y / n

,/ x
(

,/ x
(
/ n
.D2
,<
b
,
%

Y

/ nc

,/ x

/ n .32
nYthe number o! given value `.
?et us calculate a !rom the e4uation by % na & bb.,'"2 & cb.,'"
(
2, .C2
$hen n % B.
6able (. )alculation o! ratios !or relation E % !.?2.
,'" ,'"J

yy
,

,/ x,/ x
,


,/ x

yy
,

,/ x,/ x
,

" .?, A2 y .E, k5'mole2


-.D1DB31,+
-.3(C3D<<(
-.<<3<3B-3
-.+33+CBB3
(+C1.1+,<C(3,
(<<1.(CBBC,B(
(-,B.DCDC-,C<
(,,C.D1<<<(C+
,.<1B
,.BB3
,.(-<
B1D.CBCD
+,<.13C-
3,(.(D3-
b ,.<DD(<C+D ,.(1D(D+1< <(13.D<1C31,B 1,BB.<1B1<1C, 1.-3+ ,DD<.D-+D
,'"
,
% -.+13-33,1 "
,
% ,.<1B y
,
% B1D.CBCD
e.,'"
(
2 % ,.++D(C1+C e.,'"2 % (.((<B1D3, $hen n % B
c % - ,+CC.,3+B3D3C b % <-+<.+(C,(,C, a % - (((,.B1<,31,3
XQQ bonds % (((,. B1<,31,3
<-+<. +(C,(,C,
L

,+CC. ,3+B3D3C
L
(
.(2
?et us calculate !rom the e4uation:
EcYc .ethane2 % B1D.CBCD k5'mole Ec^c .ethylene2 % +,<.13C- k5'mole
Ecdc .acetylene2 % 3,(.(D3- k5'mole
Murther $e $ill sho$ determination o! distances in regular he"agon, octagon, decagon.
#n benzene molecule the carbon atoms are located in the to o! regular he"agon
.e4uilateral he"agon2, thus
,+
Mor a regular octagon:
*ccording to cosine theorem.
#! $e take ?c-c % *B % ,.1-- A !or a regular octagon, then:

,D
B
(
.
.
B
(
.
*
M
K
7
k
E
U
*M % ,.BCD A
Kk % 7K % *M
% ,.BCD A % ,.(,- A
Kk % ,.(,- A
KU % (K7 % ( ,.(,- A % (.1(- A
Kk % 7K % *M
.
sin +-
l
K*7 % +-
l
l
7* % *M
kK7 % Kk7 % +-
*ME % ,(-
l
.
.
m)
cos )7m
( (
(
% m7 & 7)
- ( m7 7)
.
o
)7m % 1<
m) % ,.B-B A
.
.
m)
cos )7m
( (
(
% m7 & 7)
- ( m7 7)
.
m) % ,.(CB A
)D
o
(
.
% m7 % 7) % ,.+C- A
)D % tg +D.< ,.1-- A % B.B3- A
?c-c % *B % ,.1-- A
)7m % 1<
o
*
B
)
7
m
)
. .
.
.
.
.
D
.
. .
o
,B<
o
)D % (
B*7 % +D.<
o
.
tg B*7 %
7)
*)
tg B*7
*B
(
. tg B*7
.
%
*) % )B, ?c-c % *B % ,.1,- A
7) % *)
7) % tg B*7
,.1,- A % B.1-1 A ?c-c % tg +D.<
7m % 7),
(
)D
% m7 % 7) % ,.D-( A
Mor a regular decagon:
*ccording to cosine theorem.

CONCLUSION
*s $e can see, three-electron bond enables to e"lain aromaticity, !ind delocalization
energy, understand aromatic bond@s seci!icity. *romatic bond in benzene molecule is
simultaneous interaction o! three airs o! central electrons $ith oosite sins through the
cycle. But $hereas central electrons are the art o! three-electron bond, then it is
ractically interaction o! si" three-electron bonds bet$een themselves, that is e"ressed in
three interactions through cycle lus si" three-electron bonds. Pe shouldn@t !orget in this
system about imortant role o! si" atom nucleuses, around $hich aromatic system is
!ormed. Kroerties o! nucleuses esecially their charge $ill in!luence on roerties o!
aromatic system.
Minally, ostulates o! the three-electrone bond theory .6B62 can be resented:
,2 * chemical bond bet$een t$o atoms may be established by means o! three electrons
$ith oositely oriented sins .8982.
,3
*
7
)
B
.
.
.
.
.
m
.
.
D
o
.
B*7 % D(
o
,.1-- A % 1.B-C A
o
,11
)D % ( 7) % tg B*7
. .
?c-c % tg D(
*) % )B, ?c-c % *B % ,.1-- A
tg B*7 %
7)
*)
7) %
tg B*7 % *)
*B
(
.
tg B*7
.
(
)D
% 7) % m7 % (.,<1 A 7m % 7),
.
.
m)
cos )7m
( (
(
% m7 & 7)
-
( m7 7)
.
m) % ,.BB, A
)7m % B+
o
898 898
* : : : * * : : : B
(2 6he electron shell o! each atom in the stable molecule, ion, radical should have such a
number o! electrone $hich corresonds to the octet. * deviation !rom the octet results in
an instability o! a article.
B2 6he state o! the three-electron bond is determined by the octet rule.
12 6he number o! electrons articiating in the chemical bond should be ma"imal and it@s
then that the energy o! the system $ill be minimal. 6aking into consideration ara < and (.
<2 #n the course o! establishing o! the chemical bond electrons .their sins2 are located in
such a $ay that enables theit interaction .attraction2 to be ma"imal.
+2 6he aromatic bond is a three-electron bond in !lat cyclic systems $ith a seci!ic
interaction o! electrons through the cycle.
#t is easy to sho$, that using three-electron bond one can e"lain aramagnetization and
structure o! o"ygen molecule, structure o! carbo"ylate anion, ozone, nahthalene and other
organic and non-organic comounds. ?et@s bring !or the e"amle structures o! some
comounds in terms o! three-electron bond.
>ahthalene
*nthracene
,C
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
.
.
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
.
.
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
. .
. .
.
.
&
&
G
G
G
&
G
G
&
&
G G
&
&
G
.
. .
. .
.
.
.
. .
. .
.
.
&
&
G

Khenanthrene
)oronene

E,3F-*nnulene
#t is interesting to note e"treme symmetry o! structures o! nahthalene, anthracene,
coronene and E,3F-annulene, that is tyical !or the ma5ority o! aromatic comounds in
general.
(-
&
G
.
&
&
&
G
G
.
.
.
.
.
.
.
.
.
.
.
. .
.
.
.
.
.
.
.
.
.
.
&
&
&
& &
G
G
G
G
G
&
&
&
G
G
G
G
&
G
.
&
&
&
G
G
.
.
.
.
.
.
.
.
.
.
.
. .
.
.
.
.
.
.
.
.
.
.
&
&
&
& &
G
G
G
G
G
&
&
&
G
G
G
G
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
/ /
/
/
/
/
&
G
.
&
&
G
G
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
&
&
&
&
&
G G
G
G
G
G
&
H H
H
H
H
H
&
G
.
&
&
G
G
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
&
&
&
&
&
G G
G
G
G
G
&
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
.
.
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
.
.
.
. .
.
&
&
G
G
G
G
&
&
.
. .
.
By the e"amle o! E,3F-annulene it is ossible to illustrate interaction through the cycle
o! central electrons o! three-electron bonds. #nteracting through the cycle, it shi!ts to the
centre in the direction o! inner atoms o! hydrogen thus increasing electron density $ithin
the cycle and decreasing outside the cycle. *nd that@s $hy outside rotons .,( V2 $ill
give signals in the area o! $eaker !ield .reduction o! electron density2, and inner .+ V2 $ill
give signals in the area o! stronger !ield .increase o! electron density2. 6hus this is
observed in reality EDF. #t also should be noted that inner rotons bracing central electrons
strengthen interaction through the cycle, and so stabilize aromatic system. But interaction
through the cycle is decisive.
#! aromatic system does not have inner rotons, then outside rotons $ill give signals in
the area o! $eaker !ield .one o! the !eatures o! aromatic comounds2.
#t is clear that in case o! antiaromatic systems $hen there is no interaction .attraction2
through the cycle, because central electrons have similar sins and ush a$ay, change in
electron density in the centre o! the cycle and outside the cycle $ill be reverse to aromatic
systems.
Murther $e $ill continue demonstration o! construction o! organic and inorganic
comounds.

Kyridine

(,
> >
&
G
&
&
G
G
&
G
>
G
G
&
&
.
. .
.
.
.
.
.
. .
.
.
Kyrimidine

Kyridazine
Kyrazine
,,B,<-6riazine

kuinoline
((
> > > >
&
G
&
&
G
G
&
G
> >
G
G
&
&
.
. .
.
.
.
.
.
. .
.
.
>
>
>
>
&
G
&
&
G
G
&
G
>
>
G
G
&
&
.
.
. .
.
.
.
.
.
.
.
.
>
>
>
>
&
G
&
&
G
G
&
G
>
>
G
G
&
&
.
. .
.
.
.
.
. . .
. .
> >
>
>
>
>
&
G
&
&
G
G
&
G
>
>
>
G
G
&
&
.
. .
.
.
.
.
.
. .
. .
>
&
G
G
&
&
G
G
&
&
G
>
.
.
.
. .
.
.
.
.
.
&
G
G
&
&
G
G
&
&
G
.
.
.
. .
.
.
.
.
.
>

#so4uinoline

#ndole

Kurine
Muran# thiohene# yrrole
(B
>
&
G
G
&
&
G
G
&
&
G
>
.
. .
. .
.
.
.
.
.
>
&
G
G
&
&
G
G
&
&
G
.
. .
. .
.
.
.
.
.
>
/
&
G
G
&
&
G
G
&
&
G
>
/
.
.
.
. .
.
.
.
.
.
&
.
>
/
&
G
G
&
&
G
G
&
G
.
.
. .
.
.
.
.
.
..
>
>
>
>
/
&
G
G
&
&
G
G
&
&
G
>
>
>
>
/
.
.
.
.
.
.
.
.
.
.
&
.
>
>
>
>
/
&
G
G
&
&
G
G
&
G
.
.
.
.
.
.
.
.
.
. .
L
L
&
G
&
&
G G
L
&
G
&
&
G G
L % 7, =, >/
.
.
.
.
. .
.
.
.
.
.
.
..
7"azole, thiazole, imidazole
Kyrazole
,,(,1-6riazole
,/-,,(,B-6riazole
(1
>
>
L
L
&
G
&
&
G G
L
&
G
&
&
G G
>
L % 7, =, >/
.
.
.
.
. .
.
.
.
.
.
.
..
>
>
/
>
>
/
&
G
&
& G
G
&
G
&
& G G
>
>
/
.
.
. .
. .
.
.
. .
.
.
..
>
>
>
/
>
>
>
/
&
G
&
&
G G
&
G
&
& G
G
>
>
>
/
.
.
. .
. .
.
.
.
.
.
.
..
>
>
>
/
>
>
>
/
&
G
&
&
G G
&
G
&
& G G
.
. . .
. .
.
.
. .
.
.
>
>
>
/
..
)ycloentadienyle anion


)arbo"ylate anion

>itro comounds
=ul!onate anion
(<
)/
G &
G
&
&
G
G
)/
. .
.
.
.
.
G
&
G
&
G
&
G
G
U )
.
.
.
.
.
.
.
.
.
.
. .
.
.
.
.
7
7
G
&
)
7
7
U
&
&
&
G
&
G
G
G
.
.
.
.
. .
.
.
.
.
.
.
.
.
.
.
7
7
>
G
&
U
U >
7
7
.
.
.
.
&
.
.
.
.
.
.
..
.
. 7
7
.
.
.
.
.
.
.
&
&
&
G
G
G
G
)
+
/
<
= 7
7
7
)
+
/
<
=
7
. .
.
G
G
&
G
&
G
7rganic acid amides and thioamides
Urea and thiourea
nuanidinium cation
=odium malon ether
(+
G
& &
.
.
.
. .
.
&
G
G
G
.
. . . .
&
> /
(
) >/
(
>/
(
/
(
> ) >/
(
.
&
&
G
G .. . .
>/
(
&
&
.
.
.
. &
.
.
.
. .
.
.
..
G
.
. 7
7
.
.
.
.
.
.
.
& &
&
&
&
& G
G
G
G
G
G
)
7
)/ )
7
7)
(
/
<
)
(
/
<
7
)
(
/
<
7
7)
(
/
<
) )/ )
G
&
>a
G
&
>a
U )
L
>/
(
U )
>/
(
L
G
&
.
.
.
.
.
.
G
.
.
.
..
.
&
&
&
G
G
L % 7, =
.
..
.
.
.
G
&
&
.
.
.
. .
.
&
G G
G
.
.
.
. . .
&
> /
(
) >/
(
L
/
(
> ) >/
(
L
..
.
.
&
&
G
G
L % 7, =
.. . .
.
.
..

=odium acetoacetic ether

*lyle cation


>itrate anion )arbonate anion =ul!ate anion

7zone
(D
G
&
&
. . . . . .
) /
(
)/ )/
(
/
(
)
)/
(
)/
&
G
G
& &
G
&
.. .
)/
B
)
7
)/ )77)
(
/
<
&
>a
G
.
.
&
)/
B
) )77)
(
/
<
)/
7
.
.
.
.
.
.
.
&
&
G
G
G
G
&
>a
&
G
&
&
&
G &
&
G
G
G
G
G
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
. .
.
.
.
.
.
>
7
7
7
&
G
&
&
&
G
&
&
G
G
G
G
G
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
. .
.
.
.
.
.
7
7
7
)
(
&
.
.
.
.
.
.
.
.
. .
.
.
.
(
=
7
&
&
&
.
.
.
.
.
.
&
&
.
.
.
.
.
.
.
.
.
.
.
.
.
G
&
&
G
7
7
7
G
G
G
G
G
G
G
&
&
&
G
&
G
G
&
G
G
.
.
. .
.
.
.
.
.
.
.
. .
.
.
.
.
.
7 7
7
7
7
7



7"ygen, aramagnetic molecule


>itrogen mono"ide, aramagnetic molecule

>itrogen dio"ide, aramagnetic molecule

>itrite anion

(3
&
G
.
&
&
&
&
G
G
.
.
. .
.
.
.
.
.
.
. 7 7
7 7
.
..
.
.
..
.
&
G
.
& &
G
.
.
. .
.
.
. .
.
. 7
> 7
..
.
. .
.
.
>7
>
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
G
>7
(
>
7 7
.
.
. .
>
7
7
&
&
G
&
&
G
G
&
&
G
.
. .
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
.
G
>7
(
>
7 7
.
.
. .
>
7
7
&
G
&
&
G
G
&
G
G
.
.
G
nrahite
*s $e can see $ith the hel o! three-electron bond structures o! abovementioned
molecules and ions are described simly and obviously by one structures, $hich
reresents the real distribution o! electrons .electron density2 in molecules .ions2.
*uthor kno$ingly did not consider a 4uestion about kinds o! !orces, that make electrons
to attract $ith oosite sins, because it is a sub5ect o! a searate consideration. *ll the
more so, because based on !amous ostulate .attraction o! t$o electrons $ith oosite
sins2 concet o! localized chemical bond !ollo$s. E"laining aromatic bond in benzene
molecule, interaction o! central electrons is strange on such long distances .(.1(- A2. But
taking into account, that electrons can sho$ $ave-like behaviour and shi!t to the center o!
benzene cycle under the in!luence o! neighbouring central electrons, this interaction looks
very truly. 6he !act o! the distance bet$een the grahite layers being B.B< A .the ;-; bond
length inside the layer making ,.1( A2 E3F may serve as an indirect con!irmation o! the
ossibility o! interaction o! the electrons through the cycle in benzene. 6his causes a $eak
bond bet$een the layers and, as a result, the ability o! the layers to shi!t relative to each
other. =ince the distance bet$een the central electrons in benzene is less and makes
(.1(- A .in case o! an interaction through the cycle2, $e should e"ect a stronger
(C
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G
&
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&
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&
&
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&
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&
&
&
&
& &
&
&
&
&
&
&
&
&
&
&
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
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G
G
G
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&
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interaction.
#t is clear that, by increasing o! cycle, distance bet$een central electrons .both
neighboring and through the cycle2 $ill increase, and that@s $hy interaction energy
through the cycle $ill decrease, and by certain distance bene!it !rom aromaticity o! system
$ill be lo$er, than energy consumtion !or creation o! lanar e4uilateral olygon .as in
the case o! cyclodecaentaene2. 6here!ore e"istence o! large aromatic monocycles $ill
deend on relation o! these t$o values.
Pith the hel o! e4uations E % a & b'? & c'?
(
and multilicity % a & b'? & c'?
(
$e can
analyze di!!erent tyes o! chemical bonds, calculate their multilicity and energy on the
basis o! e"erimental data about bonds distances.
6he tables B and 1 belo$ sho$ the a, b and c coe!!icients !or these e4uations !or the
bonds revailing in the organic chemistry .)-), )-7, )->, )-=, >->, >-7, 7-72. 6he
coe!!icients have been calculated similarly to the ;-; bonds. Using them it is ossible to
calculate the bonds multilicity and their energy .bond energy constants2 !or the most art
o! organic molecules, both aromatic and non-aromatic ones. #t makes it ossible to
calculate the aromatic comounds delocalization energy.
#t is also ossible to calculate the real molecules energy gain comared to their classic
structures. 6o do this, it is necessary to subtract the total o! the classic structure bond
energies !rom the total o! the real structure bond energies .the bond energy is calculated
$ith the E % a & b'? & c'?J e4uation2. ?et us illustrate the above taking the urea molecule
as an e"amle .leaving out o! consideration the >-/ bonds2:
B-
)lassic structure Ueal structure
?
)->
% ,.BB A, ?
)-7
% ,.(D A .32
Tultilicity )f> % , Tultilicity )f> .?%,.BB A2 % ,.+3+
Tultilicity )f7 % ( Tultilicity )f7 .?%,.(D A2 % ,.13+
E
)->
% (C,.3B1 k5'mole E,, Q.,,+F X
)->
.? % ,.BB A2 % <(B.DC- k5'mole
E
)-7
% D(3.<B3 k5'mole .!or U
(
)%72 E,, Q.,,+F E
)-7
.? % ,.(D A2 % 1C+.C1- k5'mole
E
,
% E
)-7
& (E
)->
% ,B,(.(-+ k5'mole E
(
% E
)-7
& (X
)->
% ,<11.<(- k5'mole
]E % E
(
- E
,
% ,<11.<(- k5'mole - ,B,(.(-+ k5'mole % (B(.B,1 k5'mole
=o, the energy gain !or a real urea molecule .$ith three-electron bonds2 as comared to
the classic structure makes (B(.B,1 k5'mole .<<.13D kcal'mole2. )alculations !or other
molecules may be done in the same $ay.
6his e"amle illustrates $hy the three-electron bonds aear at all: it roves to be that
the three-electron bonds are [more oor\ by energy and !ormation o! three-electron bonds
is energetically more advantageous. 6he energetic advantageousness is also the reason o!
the deviation o! the multilicity o! the three-electron bonds !rom ,.< $hich takes lace
due to either the interaction o! the three-electron bonds among themselves .!or e"amle, in
the benzene molecule2 or the interaction o! the three-electron bonds $ith the unaired
electrons located in atoms making the bond .urea molecule2. )ases are ossible $hen the
bond multilicity is changed due to the simultaneous in!luence o! the above mentioned
B,
G
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G G
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> /
(
) >/
(
7
/
(
> )
>/
(
..
.
.
&
&
G
G
.. . .
7
e!!ects.
#t should be also noted that the octet rule holds true in three-electron bond structures.
6hus, in the urea molecule the three-electron bond electrons interact artially $ith the
unaired electrons located in the atoms o! o"ygen and nitrogen. *s a result the three-
electron bond electrons do not !ully belong to the carbon atom and so the carbon atom
octet makes 3 and not C .one should not also !orget that the electronegativity o! the atoms
o! o"ygen .B.<2 and nitrogen .B2 is higher than the electronegativity o! the atom o! carbon
.(.<22.
nenerally, the octet rule de!ines the state o! the three-electron bond, that is, the
distribution o! the electrons, the energy o! their interaction $ith each other and other
unaired electrons, the !act and the e"tent o! belonging o! the three-electron bond
electrons to one or another atom.
*nd !inally, here are the values o! the a, b, c coe!!icients in the tables B and 1 !or the
Tultilicity % !.?2 and E % !.?2 e4uations.
6able B. Tultilicity % a & b'? & c'?J e4uation coe!!icients !or some tyes o! bonds.
6ye o! bond a b c
)-) --.-+-1-B1B -<.+DD3D<(C ,,.(3<+((-,
)-7 (+.-B(<(33B -D(.1+1C3,B3 <(.1B3CC(11
)-> -.+B3,DB-+ -D.<+1<<(C1 ,,.C,B31<-B
)-= <<.BB(<+<DC -,C3.3,3-D((( ,3,.3D<B33,1
>-> -.C+1-D1C( -+.+3DC,DC< C.DCBBC-,B
>-7 1+.--D<+BDD -,(B.D<+BD13< 31.DCD+B3C+
7-7 (B.3CD3+D<C -++.3<,D(D<1 13.DCB-1(<<
)-K (3.D+<13<<< -,-C.1+,(3B,( ,-D.<(3-<1BC
Tultilicity - bond multilicity,
? Y bond length in A.
B(
6able 1. E % a & b'? & c'?J e4uation coe!!icients !or some tyes o! bonds.
6ye o! bond a b c
)-) -(((,.B1<,31,3 <-+<.+(C,(,C, -,+CC.,3+B3D3C
)-7 ,,1(-.3,-<(11( -B,B<C.,D<D+B1B (((-D.-1(+<1-1
)-> -(BB(.+C<+3<3D 11<-.+,D,(,C, -3++.131,(+D,
)-= -(DDD(.+1B3<+C- C-(11.<<(D3C3D -D,1,1.<D13<D1(
>-> D-+D.,1-+<1BD -(-(D1.3,<-3B,3 ,13D3.<BD+<+B,
>-7 -+<+1.B,1,+(+( ,<3C<.<1C-D1C- -3D+C.,,+B3CDC
7-7 ,-<C-.1-313D3- -(CCB<.-(C-CB3< (,1B-.CB(DC-(B
E Y bond energy in k5'mole,
? Y bond length in A.
REFERENCES
,. #ngold m. 6heoretical essentials o! the organic chemistry. Tir, Tosco$, ,CDB, .,1B
.Uussian translation !rom: =tructure and mechanism in organic chemistry. =econd
edition, #>n7?D ).m. )ornell University ress #thaca and ?ondon, ,C+C2.
(. Tarch o. *dvanced organic chemistry. Ueactions, Techanisms, and =tructure. #n 1
volumes. Tir, Tosco$, ,C3D, vol.,, .31 .Uussian translation !rom *dvanced organic
chemistry. Ueactions, Techanisms, and =tructure. 6hird edition. oerry Tarch,
Kro!essor o! )hemistry *delhi University. >e$ `ork, ,C3<2.
B. 6.o.mats, oournal o! the *merican =ociety. 3(, BD31, .,C+-2.
1. )arey M., =undberg U. *dvanced 7rganic )hemistry. #n ( books. )hemistry, Tosco$,
,C3,, book ,, .BB< .Uussian translation !rom *dvanced 7rganic )hemistry.
Mrancis *. )arey and Uichard o. =undberg, University o! Virginia, )harlottes, Virginia.
Klenum Kress, >e$ `ork, ,CDD2.
<. o.M.T.7th, n.*nthoine, o.T.nilles, 6etrahedron ?ett. +(+<, .,C+32.
BB
+. =. Tasamune, m. /o5o, miyoti /o5o, n. Bigam, D. ?. Uabenstein, oournal o! the
*merican =ociety. CB, 1C++, .,CD,2.
D. 6ernay. p. )ontemorary organic chemistry. #n ( volumes. Tir, Tosco$, ,C3,, vol.,,
.<3B .Uussian translation )ontemorary organic chemistry. =econd edition. *ndre$
?. 6ernay. University o! 6e"as, *rlington, ,CDC2.
3. Pells *. =tructural inorganic chemistry. [Tir\, Tosco$, ,C33, vol.B, .,D-,3 .Uussian
translation !rom =tructural inorganic chemistry, !i!th Edition, Pells *. M. )larendon
Kress, 7"!ord, ,C3+2.
B1

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