IAOe?IIAEUeIA AEAAeAI?ss IAOE OE?A?IE

?INOEOOO O?CEEI-I?AAI?*II? O?I?? OA AOAEAO?I??

?i. E. I. EEOAEIAIEA

Oiaiueei ?ai? Aaneeueiae/

OAeE 547:541.124/127:541.427

IA?AO?ANIEE EI?AEssOe?EIEE AIAE?C ?AAEOe?E IOEEAIO?EUeIIAI CAI?UAIIss.
ssAEUA ?CIIA?AIAO?E*IINO? OA NO?OEOO?A IA?AO?AeIEO NOAI?A

02.00.03 – i?aai?/ia o?i?y

Aaoi?aoa?ao aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy aeieoi?a
o?i?/ieo iaoe

Aeiiaoeuee-1998

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia a Aeiiaoeueeiio aea?aeaaiiio oi?aa?neoao? I?i?noa?noaa
ina?oe Oe?a?ie

Io?oe?ei? iiiiaioe:

aeieoi? o?i?/ieo iaoe, i?ioani? A?aeia Aiaoie?e Iao?iae/, ?inoeooo o?i??
aenieiiieaeoey?ieo niieoe IAI Oe?a?ie, caa?aeoaa/ a?aeae?eo;

aeieoi? o?i?/ieo iaoe, i?ioani? ?eaa/aiei Aieiaeeie? ?aaiiae/, ?inoeooo
o?ceei-i?aai?/ii? o?i?? oa aoaeao?i?? ?i. E.I.Eeoaeiaiea IAI Oe?a?ie,
caa?aeoaa/ a?aeae?eo;

aeieoi? o?i?/ieo iaoe, aeioeaio Iae?o?a ?iiai A?eai?iae/, A?aeae?eaiiy
o?ceei-o?i?? oa oaoiieia?? ai?th/eo eiiaeei ?inoeoooo o?ce/ii? o?i?? ?i.
E.A.Iena?aeaanueeiai IAI Oe?a?ie, i?ia?aeiee iaoeiaee ni?a?ia?oiee.

I?ia?aeia onoaiiaa – Oa?e?anueeee aea?aeaaiee oi?aa?neoao, eaoaae?a
i?aai?/ii? o?i??, I?i?noa?noai ina?oe Oe?a?ie, i.Oa?e?a

Caoeno a?aeaoaeaoueny “17” 11 1998 ?. i 14 aiaeei? ia can?aeaii?
niaoe?ae?ciaaii? a/aii? ?aaee Ae 11.216.01 a ?inoeooo? o?ceei-i?aai?/ii?
o?i?? oa aoaeao?i?? ?i. E.I.Eeoaeiaiea IAI Oe?a?ie, 340114, Aeiiaoeuee,
aoe. ?.Ethenaiao?a, 70.

C aeena?oaoe??th iiaeia iciaeiieoenue o a?ae?ioaoe? ?inoeoooo
o?ceei-i?aai?/ii? o?i?? oa aoaeao?i?? ?i. E.I.Eeoaeiaiea IAI Oe?a?ie,
340114, Aeiiaoeuee, aoe. ?.Ethenaiao?a, 70.

Aaoi?aoa?ao ?ic?neaiee 15.10. 1998?.

A/aiee nae?aoa?

niaoe?ae?ciaaii? a/aii? ?aaee Oaiae?ee I.I.

CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE

Aeooaeuei?noue. I?iaeaia ?aaeoeaiino? i?aai?/ieo niieoe i?eaa?oa? oaaao
o?i?e?a i?ioyaii aaaaoueio aeanyoee?oue. Aei ioe?iee, nenoaiaoecaoe??
oa ia?aaeaa/aiiy ?aaeoeaiino? oe?iei caeo/athoueny ei?aeyoe?ei? iaoiaee.
I?ino? aii??e/i? ni?aa?aeiioaiiy e?i?eiino? a?eueieo aia?a?e, a naia
??aiyiiy A?ainoaaea, Aaiiaoa, Oaooa oa aaaaoi ?ioeo, iaee ae??oaeueia
cia/aiiy aeey noaiiaeaiiy e?euee?nieo iaoiae?a o?ceei-i?aai?/ii? o?i??.
Inoaii?i /anii aeine?aeaeaiiy ?aaeoeaiino? noa? a?eueo aeaoaeueiei a
ca’yceo c ai?iaaaeaeaiiyi ia?ao?aniiai ei?aeyoe?eiiai aiae?co. A?i
a?oioo?oueny ia aaaaoiia?aiao?iaeo ??aiyiiyo ia?ao?anii? ei?aeyoe??,
i?aeii?yaeeiaaieo i?eioeeio iie?e?i?eiino? (IIE). Aiie i?noyoue
ia?ao?ani? /eaie, ye? e?euee?nii a?aoiaothoue iaaaeeoeai? aoaeoe ??cieo
noi?nii aa??eiaaieo oaeoi??a, caaaeyei /iio cia/ii c?inoathoue ?o
ia?aaeaa/oaaeuei? iiaeeeaino? o ii??aiyii? c i?inoeie iaeiiia?aiao?iaeie
ei?aeyoe?yie. Ia?ao?aniee ei?aeyoe?eiee aiae?c aea? ciiao aeine?aeeoe
iia?, ?ai?oa iaa?aeii? oi?eaeuei? aeanoeaino? ?aaeoe?eieo na??e, iii?ae
yeeo iaea?eueoo oaaao i?eaa?oa? ?ciia?aiao?e/i?noue. Noiniaii i?aai?/ieo
?aaeoe?e oeae oa?i?i icia/a? ioeueia? aaee/eie eiao?oe??io?a /ooeeaino?
iaeiiia?aiao?iaeo ei?aeyoe?e, iai?eeeaae ? (a) o ??aiyii? Aaiiaoa
(A?ainoaaea), a ?ciia?aiao?e/ieo oi/eao (?IO), ui oa?aeoa?ecothoue
ia?aiao?e no?oeoo?e, ?ic/eiieea oa ?ioeo aioo??oi?o aai ciai?oi?o
oaeoi??a, a oaeiae ci?io ciae?a oeeo eiao?oe??io?a, oiaoi ?iaa?n?th
?aaeoeaiino?, i?ney ia?aoiaeo /a?ac a?aeiia?aei? ?IO (ia?aaeien
?ciia?aiao?e/iino?).

?ciia?aiao?e/i?noue ? aeeeeeii o?aaeeoe?eiei oyaeaiiyi o o?i??. Aei
iaoeo aeine?aeaeaiue aoaeue-ye? aenia?eiaioaeuei? aeieace yaeua
?ciia?aiao?e/iino? aoee iaa?aeii?. Oiio caii/aoeiaaia o ?iaio?
nenoaiaoe/ia aea/aiiy ?ciia?aiao?e/ieo aeanoeainoae nenoai
ioeeaio?eueiiai cai?uaiiy ? aeooaeueiei. Aiii aaciina?aaeiuei iia’ycaia
c i?iaeaiith oeoia/aiiy iaoai?noe/ii? noo? ni?aa?aeiioaiue ia?ao?anii?
ei?aeyoe??, a naia c aeei?enoaiiyi ?o aeey c’ynoaaiiy iaoai?ci?a
ioeeaio?eueieo ?aaeoe?e.

Iacaaaeath/e ia oa, ui oe? aeiyoeiai aaaeeea? a o?i?? ? a?io?i??
?aaeoe?? ?ioaineaii aea/athoueny i?ioyaii inoaii?o 60-70 ?ie?a, ie?ai?
aniaeoe ?o iaoai?ci?a ana ua caeeoathoueny i?iaeaiaoe/ieie. Aein?
o?eaathoue aeeneon?? noiniaii o/ano? oao?aaae?e/ieo i?ii?aeieo
i?iaeoeo?a o i?ioeanao aoeeethaaiiy, ?ie? eiiieo ?ioa?iaae?ao?a o
aaoa?ie?oe/ieo i?ioeanao, ni?aa?aeiioaiiy aeae?eueeio iaoai?ci?a o
iaaeao iaeiiai e oiai ae ia?aoai?aiiy, noi?aeieo aai ci?oaieo
iaoai?ci?a. Oaea oeueiai ia?ae?eo aeinoaoiuei, uia ia?aeiiaoeny a
aeioe?eueiino? aeine?aeaeaiiy iaoai?ci?a ioeeaio?eueiiai cai?uaiiy c
canoonoaaiiyi iaoiaeo ia?ao?aniiai ei?aeyoe?eiiai aiae?co.

Aeena?oaoe?eia ?iaioa aeeiioaaeany a?aeiia?aeii aei eii?aeeiaoe?eii?
i?ia?aie AI O?N? oa I?iaoco O?N? ii i?iaeai? “Oai??y o?i?/ii? aoaeiae,
?aaeoe?eia caeaoi?noue, e?iaoeea”, a oaeiae i?aeaoc?anueei? iaoeiai?
i?ia?aie I?i?noa?noaa ina?oe Oe?a?ie ca?aeii c oaiaoe/ieie ieaiaie
Aeiiaoeueeiai aea?aeaaiiai oi?aa?neoaoo (? aea?aeaaii? ?a?no?aoe?? oai
811044163, 01860099073, 01 95U0 15723).

Iaoith ?iaioe ? ?icaeoie iiaiai iai?yio aeine?aeaeaiiy iaoai?ci?a
?aaeoe?e ioeeaio?eueiiai cai?uaiiy i?e iane/aieo oa iaiane/aieo
aeaeo?io?eueieo aoaeaoeaaeo oeaio?ao c canoinoaaiiyi ia?ao?aniiai
ei?aeyoe?eiiai aiae?co. Oey iaoa aeinyaaeanue iine?aeiaiei ?ica’ycaiiyi
ianooiieo caaea/: a) aeine?aeeoe noi?niee aieea ia oaeaee?noue ?aaeoe??
ioeeaio?eueiiai cai?uaiiy ??cieo ia?ao?anii aa??eiaaieo oaeoi??a; a)
noai?eoe iie?e?i?ei? ?aa?an?ei? iiaeae?, ye? aaeaeaaoii iienothoue
ia?ao?ani? ?aaeoe?ei? na???; a) io?eiaoe aenia?eiaioaeuei? aeieace yaeua
?ciia?aiao?e/iino?; a) ai?iaaaeeoe aeei?enoaiiy ?acoeueoao?a
ia?ao?aniiai ei?aeyoe?eiiai aiae?co aeey ?aeaioeo?eaoe?? iaoai?ci?a.

Ia’?eoe aeine?aeaeaiiy: a?iieaeoey?i? ?aaeoe?? aaici?e-, aaicee- oa
aaica?ae?eeaaeiaai?ae?a, a oaeiae aaiceeaaicienoeueoiiao?a c
a?aeiia?aeieie ioeeaio?eaie (ia?aeii?, aoi?eii?, o?aoeii? ai?ie
a?iiaoe/iiai, aee?ii-a?iiaoe/iiai oa ae?oaoe/iiai ?yae?a, i??eaeeie,
?i?aeaciee) o ianiaoeeo?/ii ? niaoe?o?/ii nieueaaooth/eo ?ic/eiieeao i?e
??cieo oaiia?aoo?ao.

Iaoiaee aeine?aeaeaiiy. Aei eiio?ieth oaeaeeino? ?aaeoe?e caeo/ai?
ianooii? iaoiaeeee: a) iioaioe?iiao?e/ia i?o?eoia oeo?oaaiiy ia?aeiieo ?
aoi?eiieo a?eeai?i?a; a) iioaioe?iiao?e/ia a?aaioiiao?e/ia aecia/aiiy
eiioeaio?aoe?? aaeiaai?ae-ai?ii?a (Cl–, Br–); a) eiiaeoeoiiao?e/ia
aecia/aiiy eiioeaio?aoe?? eii?a, ui iaeiie/othoueny ca ia?aa?aii
?aaeoe?e; a) niaeo?ioioiiao?e/iee eiio?ieue eiioeaio?aoe?? caaa?aeaieo
a?eeai?i?a.

Iaoeiaa iiaecia. Aia?oa a i?aeoeoe? o?ceei-i?aai?/ii? o?i?? i?iaaaeaii
eiiieaenia nenoaiaoe/ia aeine?aeaeaiiy noi?niiai aieeao ??cieo
ia?ao?anii aa??eiaaieo oaeoi??a ia oaeaee?noue ? iaoai?cie
a?iieaeoey?ieo ?aaeoe?e ioeeaio?eueiiai cai?uaiiy a aaici?eueiiio,
aaiceeueiiio oa aaica?ae?eeueiiio noano?aoao. Ia i?aenoaa? iaoiaeieia??
ia?ao?aniiai ei?aeyoe?eiiai aiae?co io?eiaii iia? ciaiiy uiaei
?aaeoeaiino? nenoai ioeeaio?eueiiai cai?uaiiy, ye? iathoue
ooiaeaiaioaeueia cia/aiiy aeey ?icaeoeo e?euee?nii? oai??? i?aai?/ieo
?aaeoe?e. Ciaeaeaii ?ai?oa iaa?aeii? aeanoeaino? ia?ao?anieo ?aaeoe?eieo
na??e: iaaaeeoeai?noue aoaeo?a ia?ao?anii aa??eiaaieo oaeoi??a, oaiiiai
?ciia?aiao?e/iino? (?IO, ia?aoiaee /a?ac ?IO), oi/ee iaaca?iiae??, aea
aeeiio?oueny i?eioeei aaeeoeaiino?. Cai?iiiiiaaii ?ioa?i?aoaoe?th
oaiiiaia ?ciia?aiao?e/iino?: ?IO o?aeoothoueny ye e?euee?ni? ?iaeaene
no?oeoo?e ia?ao?aeieo noai?a (IN), a eiao?oe??ioe ia?ao?anii? aca?iiae??
– ye e?euee?nia i??a ci?ie no?oeoo?e IN. ?ic?iaeaii iie?e?i?ei?
iaoaiaoe/i? iiaeae? ?aaeoeaiino? aeine?aeaeaieo nenoai, ye? aeathoue
ciiao ciaeoe aiaeia??, iniaeeaino? oa a?aei?iiino? iaoai?ci?a
ioeeaio?eueiiai cai?uaiiy i?e ??cieo aeaeo?io?eueieo aoaeaoeaaeo
oeaio?ao, a oaeiae aecia/eoe oiiae ?aae?caoe?? ?iaeea?aeoaeueieo
iaoai?ci?a. Iaa?oioiaaii iieiaeaiiy i?i aea? iaeano? iaoai?ci?a
ioeeaio?eueiiai cai?uaiiy ca o/anoth aaici?eoei?eae?a, aea a caeaaeiino?
a?ae iiey?iino? ai?ioiiieo ?ic/eiiee?a oa no?oeoo?e ?aaeoaio?a
ooai?ththoueny ??ci? ca i?e?iaeith IN, iiey?i? iaoeeee?/i? oa iaiiey?i?
oeeee?/i? c I-ca’yceii. Aecia/aii oiiae cae?eniaiiy caaaeueiiai aeey
an?o noano?ao?a iaoai?cia ocaiaeaeaiiiai cai?uaiiy SN2 oeio.
Iinooeueiaaii aeaa ia?o?ooe ioeeaio?eueiiai cai?uaiiy a ?aaeoe?yo
aaica?ae?eea?ii?ae?a – ca o/anoth aeo?aeiiai noano?aoo (SN2 iaoai?ci) oa
u?eueii? eiiii? ia?e — aaica?ae?ee?e a?ii?aeo ( SN2 – IP iaoai?ci).
Caeiaooi aeai?, ui na?ae/aoue i?i ia?aa?a eii-ia?ieo ?aaeoe?e /a?ac
oeeee?/i? IN c I-ca’yceii.

Iaoeiaa ? i?aeoe/ia cia/ei?noue. Ciaeaeai? e?iaoe/i? caeiiii??iino?
?aaeoe?? ioeeaio?eueiiai cai?uaiiy caeeaaeathoue i?aeaaeeie
ooiaeaiaioaeueieo i?aeoiae?a aei nenoaiaoecaoe?? oa ia?aaeaa/aiiy
?aaeoeaiino? c o?aooaaiiyi iaaaeeoeaieo aoaeo?a ia?ao?anii aa??eiaaieo
oaeoi??a a aeoeaioe?eieo i?ioeanao, ?icoe?ththoue iiaeeeaino?
?aeaioeo?eaoe?? iaoai?ci?a c o?aooaaiiyi ?o ci?ie o caeaaeiino? a?ae
no?oeoo?e ?aaeoaio?a, aeanoeainoae ?ic/eiiee?a ? oaiia?aoo?e. Aaaeeeaa
oai?aoe/ia ? i?aeoe/ia cia/aiiy iathoue aenia?eiaioaeuei? aeieace yaeua
?ciia?aiao?e/iino?, ?aae?caoe?y oe?eiai niaeo?a ?IO, oi?eaeuei?
ia?aoiaee /a?ac ?IO, anoaiiaeaiiy e?eoe/ieo aaee/ei ia?aiao??a iaeieo
aa??eiaaieo oaeoi??a, i?e yeeo cieeathoue iaaaeeoeai? aoaeoe ?ioeo.
Ciaiiy oeeo ?ai?oa iaa?aeiieo aeanoeainoae ia?ao?anieo ?aaeoe?eieo na??e
nooo?ai iioe?th? oa iiaeeaeth? o?aaeeoe?ei? oyaeaiiy i?i ?aaeoeai?noue,
i?aei?ia? ?o ia ye?nii iiaee ??aaiue, caaacia/o? iaoeiai iaa?oioiaai?
i?aeoiaee aei ieaioaaiiy iioeiaeueieo oiia cae?eniaiiy i?aeoe/ii
aaaeeeaeo ioeeaio?eueieo i?ioean?a c o?aooaaiiyi ?o iaoai?ci?a. ?iaioa
ia? oe?iea aeciaiiy, i?i ui na?ae/eoue oeeooaaiiy ?? ?acoeueoao?a a?eueo
i?ae o 200 noaooyo oa iecoe? iiiia?ao?e.

Iieiaeaiiy, ui caoeuathoueny: a) iaaaeeoeai?noue aoaeo?a ia?ao?anii
aa??eiaaieo oaeoi??a; a) ia’?eoeai?noue yaeua ?ciia?aiao?e/iino?; a)
ia?ao?aniee ei?aeyoe?eiee aiae?c ye aoaeoeaiee iaoiae aea/aiiy
iaoai?ci?a ?aaeoe?e oa no?oeoo?e IN. Ia i?aenoaa? oeeo iieiaeaiue
caii/aoeiaaii iiaee iaoeiaee iai?yiie e?euee?niiai aeine?aeaeaiiy
iaoai?ci?a ?aaeoe?e ioeeaio?eueiiai cai?uaiiy.

Ai?iaaoe?y ?iaioe. Iniiai? ?acoeueoaoe ?iaioe aeiiia?aeaeeny oa
iaaiai?thaaeeny ia Ananithci?e ia?aae? “Iaoaieciu aaoa?ieeoe/aneeo
?aaeoeee” (Eai?ia?aae – 1974), 12, 13 Oe?a?inueeeo ?anioae?eaineueeeo
eiioa?aioe?yo c o?ce/ii? o?i?? (Ee?a – 1977, Iaeana – 1982), 12, 13, 14
oa 15 Oe?a?inueeeo ?anioae?eainueeeo eiioa?aioe?yo c i?aai?/ii? o?i??
(Oaeai?iae – 1974, Aeiiaoeuee – 1978, Iaeana – 1983, Oaeai?iae – 1986),
17 Oe?a?inuee?e eiioa?aioe?? c i?aai?/ii? o?i?? (Oa?e?a – 1995), III
Neiiic?oi? c o?i?? oa oaoiieia?? aaoa?ioeeee?/ieo niieoe ai?th/eo
eiiaeei (Aeiiaoeuee – 1978), eiioa?aioe?? “?aaeoeeiiiay niiniaiinoue
aceiia” (Iiainea??nuee – 1979), II Ananithci?e eiioa?aioe?? c o?i??
aaoa?ioeeee?/ieo niieoe (?eaa – 1979), Ananithci?e ia?aae? “Iaoaieciu
?aaeoeee ioeeaioeeueiiai caiauaiey” (Aeiiaoeuee – 1983), I Ananithci?e
eiioa?aioe?? “Oeiey e i?eiaiaiea iaaiaeiuo ?anoai?ia” (?aaiiai – 1986),
Ananithci?e ia?aae? “Iaoaieciu ?aaeoeee ioeeaioeeueiiai caiauaiey e
i?eniaaeeiaiey” (Aeiiaoeuee – 1991), 73-io c’?cae? Ei?aenueeiai
o?i?/iiai oiaa?enoaa oa 4-io Neiiic?oi? “Iieaeoey?ia no?oeoo?a –
?aaeoe?eia caeaoi?noue” (?i/ii, ?anioae?ea Ei?ay, 1994); aoee iiaeai? ye
oace aeiiia?ae? ia 4 eiioa?aioe?th IUPAC c o?ceei-i?aai?/ii? o?i??
(Ei?e, Aiae?y, 1978).

Ioae?eaoe??. Ca oaiith aeena?oaoe?? iioae?eiaaii 32 noaoo? oa oace 20
aeiiia?aeae.

Aeaeea?aoe?y iniaenoiai aianeo aeena?oaioa. Aeena?oaioo iaeaaeeoue
ae??oaeueia ?ieue o aecia/aii? iaoe aeine?aeaeaiiy oa ie?aneaii? caaea/
?? ?aae?caoe??, ieaioaaii? oa aeeiiaii? aaaaoioaeoi?ieo e?iaoe/ieo
aenia?eiaio?a, ia?iaoe? aenia?eiaioaeueieo aeaieo, ?o ?ioa?i?aoaoe??,
ocaaaeueiaii? ?acoeueoao?a, oi?ioethaaii? iniiaieo iieiaeaiue oa
aeniiae?a, ye? caoeuathoueny. *anoeia ?iaioe aeeiiaia i?ae ea??aieoeoaii
aeena?oaioa nooaeaioaie (Oeoiie?iaa A.?., Eo?aiia I.I., Aiaeeai? O.A.,
Ei?aeeeiaa I.?., ?ono E.I., Oaaae I.I., *aoaa?iaa I.A.) oa ani??aioaie.
Inoaii? caenoeee o?e eaiaeeaeaonuee? aeena?oaoe?? (Aii/a?ia I.I.,
Eeoiiaiaiei E.?., Na?aa?yeia ?.I.), iaoeiaei ea??aieeii yeeo ?
aeena?oaio. ?aaeoe?? aaiceeaaicienoeueoiiao?a c ai?e?iaie aea/aeeny
ni?eueii c i?io. E? oa eiai ni?a?ia?oieeaie a oi?aa?neoao? ?iaa
(i.?i/ii, ?anioae?ea Ei?ay). E?iaoe/i? iniaeeaino? ?aaeoe?e
aaica?ae?eea?ii?ae?a c a?eeai?iaie aeine?aeaeai? ca o/anoth i?io.
Ie?eieea I.I.. Iiaeaethaaiiy iiaa?oi? iioaioe?eieo aia?a?e i?aeeiiieo
aca?iiae?e o oe?eueieo eiiieo ia?ao aaeiaai?ae?a aaica?ae?ee?th
i?iaaaeaii ?acii c Iai/aiei A.A.. Aeeiiaiith oe??? ?iaioe ia ii/aoeiaiio
aoai? ni?eyea aaeeea ?ioaeaeooaeueia i?aeo?eiea a/eoaey aeena?oaioa
aeaaeai?ea AI O?N? Eeoaeiaiea E.I..

Iaoiaeieia?y aeine?aeaeaiiy. ?iaioa a?oioo?oueny ia iaoiaeieia??
ia?ao?aniiai ei?aeyoe?eiiai aiae?co oe?eani?yiiaaiiai aaaaoioaeoi?iiai
e?iaoe/iiai aenia?eiaioo.

Ianya oa no?oeoo?a aeena?oaoe??. ?iaioa aeeeaaeaia ia 317 noi??ieao
iaoeiiieniiai oaenoo, i?noeoue 62 oaaeeoe?, 41 ?enoiie oa neeaaea?oueny
?c anooio, naie ?icae?e?a, aeniiae?a, ia?ae?eo e?oa?aoo?ieo aeaea?ae,
yeee i?noeoue 275 iaeiaioaaiue. O ia?oiio ?icae?e? ?icaeyiooi a
?noi?e/iiio aniaeo? aii??e/i? i?aeoiaee aei aea/aiiy no?oeoo?e IN,
e?eoe/ii i?iaiae?ciaaii no/aniee noai i?iaeaie, ?ic?iaeaii iaoiaeieia?th
aeei?enoaiiy ei?aeyoe?eiiai aiae?co aeey oa?aeoa?enoeee IN. Ae?oaee
?icae?e i?noeoue iien aeei?enoaieo o ?iaio? iaoiae?a oa iaoiaeee
aenia?eiaioaeueieo aeine?aeaeaiue. O o?aoueiio ?icae?e? iiaeaii
?acoeueoaoe aeine?aeaeaiiy noi?niiai aieeao no?oeoo?e ?aaeoaio?a,
iiey?iino? na?aaeiaeua oa oaiia?aoo?e ia ?aaeoeai?noue nenoaie
aaici?eaaeiaai?aee – a?eeai?ie a oiiaao ianiaoeeo?/ii? nieueaaoaoe??,
iaaaaeaii aenia?eiaioaeuei? aeieace yaeua ?ciia?aiao?e/iino? oa
cai?iiiiiaaii eiai ?ioa?i?aoaoe?th. *aoaa?oee ?icae?e i?enay/aiee
aea/aiith ia?ao?aniiai aieeao no?oeoo?ieo oaeoi??a oa na?aaeiaeua ia
e?iaoeeo ?aaeoe?e aaici?eoei?eae?a c ai?e?iaie a oiiaao niaoe?o?/ii?
nieueaaoaoe??. O i’yoiio ?icae?e? ?icaeyiooi e?euee?ni? caeiiii??iino?
noi?niiai aieeao no?oeoo?ieo oaeoi??a, iiey?iino? ai?ioiiieo ?ic/eiiee?a
oa oaiia?aoo?e ia ?aaeoe?eio caeaoi?noue nenoaie aaiceeuei? noano?aoe
(aaiceea?ii?aee, aaiceeaaicienoeueoiiaoe) – ai?ie. Iniaeeaino? e?iaoeee
oa iaoai?ci?a ?aaeoe?e aaica?ae?eeaaeiaai?ae?a c a?eeai?iaie a
ai?ioiiieo ?ic/eiieeao o caeaaeiino? a?ae eiioeaio?aoe?eieo oa
no?oeoo?ieo oaeoi??a aena?oeaii a oinoiio ?icae?e?. Nueiiee caeeth/iee
?icae?e i?noeoue ii??aiyeueiee aiae?c iaoai?ci?a aeine?aeaeaieo
?aaeoe?e.

INIIAIEE CI?NO AeENA?OAOe??

– eiao?oe??ioe ia?ao?anieo /eai?a, ye? a?aoiaothoue aca?iiae?? i?ae
aa??eiaaieie oaeoi?aie, iicia/aieie ieaei?ie ?iaeaenaie; aa?oi? ?iaeaene
noinothoueny o?eniaaieo oaeoi??a.

(1)

(2)

, (3)

(4)

(5)

(6)

(7)

(8)

, (9)

(10)

?AAEOe?? AAICI?EUeIEO ? AAICEEUeIEO NOANO?AO?A O AI?IOIIIEO ?IC*EIIEEAO

. Inoaii? aeaco? ia oa, ui ca?yaee ia a?aeiia?aeieo ?aaeoe?eieo
oeaio?ao o IN ? i?eaeecii oae?, ye a ?aaeoaioao. Oea aea? ciiao c?iaeoe
a?oioiaai? aeniiaee uiaei aoaeiae IN a ?IO oa i?iaiae?coaaoe, aeoiaey/e
c ??aiyiue (11,12), ci?io no?oeoo?e IN i?ae aieeaii cai?niee?a X ? Y.
Oae? aa??aoe?? no?oeoo?e IN ca?aathoueny c ia?aaeaa/aieie ca aeiiiiiaith
ae?aa?aie Ii? I’Oa??aea-Aeaeaiena (?en.1)

(11)

(12)

= 0.

(+ (- (

XC6H4(H2) N … Q … LG (13)

C6H4Y

(+ (- (

XC6H4(H2) N … Q … LG
(14)

C6H4Y

(+ (-
(

XC6H4(H2) N … Q … LG
(15)

C6H4Y

, a?aeaoaa?oueny a i?ioeeaaeieo iai?yieao.

, oiaoi a iiai?e i??? aenia?eiaioaeueii aeiaaaeaia ?aaeuei?noue yaeua
?ciia?aiao?e/iino?. O oaae.2

Oaaeeoey 1

Eiao?oe??ioe ??aiyiiy (6)1) aeey ?aaeoe?e ai?e?i?a (XC6H4NH2) c
Y-cai?uaieie aaici?eueieie, aaiceeueieie oa aaica?ae?eeueieie
noano?aoaie a ai?ioiiieo ?ic/eiieeao (Ac — aaicai, IA — i?o?iaaicai, OA
— oei?aaicai, OeA- oeeeeiaaenai, AeI — ae?ienai)

( 0)

1 YN6I4COBr Ac (25) 1.10(0.07 3.00(0.03 0.79(0.08 1.392) 3.79

2 YC6H4COBr OA:OeA

1:1 (25) 0.58(0.12 3.16(0.04 0.62(0.13 0.942) 5.10

3 YC6H4COCl IA (25) 1.36(0.06 2.72(0.09 0.30(0.02 4.53 9.07

4 YC6H4COCl OA (25) 0.88(0.04 3.23(0.05 0.57(0.10 1.54 5.67

5 YC6H4COCl Ac (25) 1.04(0.03 3.43(0.07 0.65(0.08 1.60 5.28

6 YC6H4COCl OA:OeA, 1:1 (25) 1.14(0.06 3.32(0.04 0.80(0.09 1.422) 4.15

7 YC6H4CH2Br 1I AeINI

a IA (40) 0.22(0.14 1.40(0.04 0.57(0.07 0.392) 2.46

8 YC6H4CH2Br 2I AeINI

a AeI (40) 0.39(0.03 1.22(0.03 0.61(0.07 0.642) 2.03

9 YC6H4CH2Br 3I AeINI

( 0)

10 YC6H4CH2Br IA (40) -0.29(0.03 1.90(0.03 0.48(0.06 -0.602) 3.99

11 YC6H4CH2Br AeI (40) -0.39(0.02 2.31(0.03 1.77(0.06 -0.222) 1.30

12 AAN3) AeINI:OAO, 1:3 (20) -0.25(0.02 2.03(0.02 0.53(0.05 -0.472) 3.83

13 AAA4) IA (40) -0.87(0.09 1.59(0.20 0.80(0.29 -1.08 1.99

____________________

1) Eiao?oe??ioe ia?ao?anii? ei?aeyoe?? R ( 0.997.

2) Aenia?eiaioaeueii ?aae?ciaai? ?IO.

3) YC6H4CH2OSO2C6H5.

aeey cai?niee?a Y a (YC6H4)2CHBr.

iaeiiia?aiao?iaeo ei?aeyoe?e

(1) o aeayeeo ?aaeoe?eieo na??yo i?ae aieeaii ??cieo o?eniaaieo
cai?niee?a O a ai?e?iao.

+ — +

XC6H4NH2-Q-LG YC6H4-Q-NH2C6H4X,

| LG—

C6H4Y

XC6H4NH2, XC6H4NH2,

YC6H4-Q-LG YC6H4-Q+, LG—

?en. 1 — Aa??aoe?? no?oeoo?e IN ?aaeoe?e aaici?eueieo (Q=CO, LG= Cl, Br)
? aaiceeueieo (Q=CH2, LG=Br, OSO2C6H5) noano?ao?a c ai?e?iaie a
ai?ioiiieo ?ic/eiieeao (iiyniaiiy aeea. o oaeno?)

caaaeyee ?iaa?n?? ?aaeoeaiino? noano?aoo. Oea iaeiia??ia c
i?oiaeienaeueiiai iiaeyaeo yaeua iia’ycaia c aa??aoe??th no?oeoo?e IN a
iaaeao iaeiiai e oiai ae SN2 iaoai?cia.

.

a YC6H4CH2OSO2C6H4Z) aeei?enoaii ni?aa?aeiioaiiy

(16)

(17)

Oaaeeoey 2

a ei?aeeyoe?yo (1) aeey ?aaeoe?e O-cai?uaieo ai?e?i?a c Y-cai?uaieie
aaici?eueiei oa aaiceeueiei noano?aoaie

N 21) N 71) N 91)

H 0 0.63 ( 0.09 0.22 ( 0.04 0.26 ( 0.02

3-Cl 0.37 0.42 ( 0.03 0 0.12 ( 0.01

3-NO2 0.71 0.16 ( 0.02 -0.14 ( 0.01 -0.16 ( 0.01

5-NO2-3-NOOCH3 0.96 0 -0.35 ( 0.06 –

3,5-(NO2)2 1.42 -0.37 ( 0.04 – –

[0.94]

[0.39]

[0.49]

_____________

1) Iiia? a?aeiia?aea? ?aaeoe?ei?e na??? a oaae. 1.

Eiao?oe??ioe ia?ao?anii? aca?iiae?? qxz ? (xz ? i??ith
ae??ocaiaeaeaiiino? ooai?aiiy oa ?ic?eao ca’yce?a a IN i?ioean?a
ioeeaio?eueiiai cai?uaiiy. ?o noaoecoe/ia cia/ei?noue, nooo?aa
a?aei?ii?noue a?ae ioey oa aeiaeaoiee ciae o aeine?aeaeaieo ia?ao?anieo
na??yo [qxz = 0.22 ( 0.08, 0.47 ( 0.09 a?aeiia?aeii aeey ?aaeoe?e
3-NO2-aaici?eaaeiaai?ae?a o aaicai? (Ac, 25 0N) ?
4-NO2-aaiceeaaeiaai?ae?a o i?o?iaaicai? (IA, 40 0N), (xz = 0.24 ( 0.06
aeey ?aaeoe?e 4-NO2-aaiceeaaicienoeueoiiao?a o noi?o? AeINI-OAO (1:3, 20
0N)] na?ae/aoue, ye ? iiia?aaei? aeai? (oaae. 1), i?i ni?eueiee aeey
aaici?eueieo oa aaiceeueieo noano?ao?a SN2 iaoai?ci.

( 0.

, (18)

Ni?euei?noue SN2 iaoai?cia ?aaeoe?e aaici?eoei?eae?a (YC6H4COCl) c
a?eeai?iaie a IA, oei?aaicai? (OA) oa ?o noi?oao (na?aaeiaeua A) ?
aaiceea?ii?ae?a (YC6H4CH2Br) c i-aooeeai?iii a IA, OA oa a?ia?ieo
noi?oao OA c IA ? oeeeeiaaenaiii (OeA) i?aeoaa?aeaeo?oueny iaeiaeiaei
aeey ieo aeiaeaoiei ciaeii eiao?oe??ioa qys (oaae. 3), yeee a?aoiao?
aca?iiae?th i?ae cai?nieeaie Y ? iiey?i?noth na?aaeiaeua ca?aeii c
??aiyiiyi (8). Ii?yae c oeei aeey aiaeia?/ieo ?aaeoe?e aaici?eoei?eae?a
o OeA ? eiai noi?oao c OA (na?aaeiaeua A) qys ( 0 (oaae. 3). I?e/eia
ci?ie ciaea qys iieyaa? a iiya? a iaeiiiey?iiio na?aaeiaeu? A oeeee?/ieo
IN (19) c I-ca’yceii.

O (

XC6H4(H/CH3) N (((( C ( C6H4Y (19)

H (((( Cl

I?i ii?ooaiiy iaeii??aeiino? IN i?e ia?aoiae? a?ae na?aaeiaeua A aei A
na?ae/aoue ceiie iaeiiia?aiao?iaeo ei?aeyoe?e (4), i?eeeaaee yeeo
iaaaaeai? ia ?en. 3 ? 4, a oaeiae oie i?eioeeiiai aaaeeeaee oaeo, ui oe?
?aaeoe?? a na?aaeiaeuao A ? A iaeaaeaoue aei ??cieo ia?ao?anieo
?aaeoe?eieo na??e, ui iienothoueny a?aeiia?aeii aei ??aiyiiy (10)
iie?e?i?eieie ?aa?an?yie 1 ? 2 (oaae. 4). *a?ac oa ui I-ca’ycie aeoaea
/ooeeaee aei aieeao aeaeo?iiieo aoaeo?a cai?niee?a X, Y oa iiey?iino?

?ic/eiiee?a, o ?aaeoe?yo, ui a?aeaoaathoueny a na?aaeiaeu? A,
niinoa??aathoueny a oe?eiio a?eueo ?ioaineai? ia?i? aca?iiae?? oeeo
oaeoi??a, a oaeiae aca?iiae?y o?aoueiai nooiaiy ii??aiyii c oeie, ui
cao?eniaai? i?e aeei?enoaii? na?aaeiaeua A, aea ?aae?cothoueny IN oeio
(13) aac I-ca’yceo.

= 0.459 a

Oaaeeoey 3

Eiao?oe??ioe ??aiyiiy (8) aeey ?aaeoe?e aaici?eoei?eae?a c a?eeai?iaie a
IA, OA ? ?o noi?oao (na?aaeiaeua A) oa a OeA ? eiai noi?oao c OA
(na?aaeiaeua A) i?e 25 0N, a oaeiae aeey ?aaeoe?e aaiceea?ii?ae?a c
i-aooeeai?iii o na?aaeiaeuao A ? A i?e 40 0N

Na?aaeiaeua

YC6H4COCl + 3-FC6H4NH2

1 -1.4 ( 0.3 13.6 ( 0.3 6.9 ( 0.6 0.998 -1.97 0.20 A

2 3.1 ( 0.2 7.0 ( 0.6 -6.6 ( 0.7 0.993 1.061) 0.47 A

YC6H4COCl + 3-BrC6H4NHCH3

3 0.3 ( 0.1 7.1 ( 0.1 2.0 ( 0.3 0.998 -3.55 0.15 A

4 3.3 ( 0.2 8.4 ( 0.8 -6.0 (0.8 0.999 1.401) 0.55 A

YC6H4CH2Br + Bun-NH2

5 -4.0 ( 0.3 12.8 ( 0.3 8.7 ( 0.6 0.999 -1.47 0.4591) A, A

__________

1) ?aae?ciaai? ?IO.

( 0.

*a?ac oa, ui i?oei?noue I-ca’yceo a IN (19) caeaaeeoue cie?aia a?ae
iiey?iino? ?ic/eiieea oa

Oaaeeoey 4

Eiao?oe??ioe ??aiyiiy (10) aeey ?aaeoe?e aaici?eoei?eae?a (cai?nieeeY) c
ai?e?iaie (cai?nieee O) a na?aaeiaeuao A (?aa?an?y 1) ? A (?aa?an?y 2)
i?e 25 0N

6.5 ( 0.7 -8.8 ( 0.9

qxys 2.0 ( 0.2 6.9 ( 2.5

R 0.998 0.998

s0 0.069 0.082

n/n0 99/104 57/57

= 0 a ??aiyii? (4)], ioaea iiey?i?noue IN (19) oaea naia, ye ?
iiey?i?noue ?aaeoaio?a. Oe? oa ?io? iaaaaeai? a aeena?oaoe?? aeai?
aeia?a ocaiaeaeothoueny c oeeee?/iith no?oeoo?ith IN (19).

lg kso = (-10 ( 3) + (37.0 ( 9.7)ps + (2.7 ( 1.0)103/T + (-11.6 (
0.9)ps103/T , (20)

= 0.233

Iineethth/e /e ineaaethth/e I-ca’ycie a OeIN (19) ca aeiiiiiaith
aa??thaaiiy no?oeoo?ieo oaeoi??a, iiey?iino? na?aaeiaeua A, a oaeiae
oaiia?aoo?e iiaeia oe?eani?yiiaaii ci?ithaaoe aeaoae? eiai no?oeoo?e o
a?aeiia?aeiino? aei caeiiii??iinoae, ye? iaoiiaeai? ciaeaie oa
aaee/eiaie ?icaeyiooeo eiao?oe? ?io?a ia?ao?anii? aca?iiae??, aai a
ie?aieo aeiaaeeao ia?aoai?thaaoe eiai a iaoeeee?/io oi?io (13) iaa?oue a
iaeiiiey?ieo ?ic/eiieeao. I?ei??ii, c i?aeaeuaiiyi oaiia?aoo?e, /e c
aaaaeaiiyi o iieaeoeo noano?aoo AAeC ceiie ei?aeyoe?? (3) aeey ?aaeoe?e
aaici?eoei?eae?a c N-CH3-ai?e?iaie noathoue iaio iii?oieie, aai e cian?i
cieeathoue (?en.3). Oe? ?acoeueoaoe ia?aeiiothoue o oiio, ui iaa?oue o
na?aaeiaeua A, ni?eyoeeaiio aeey oi?ioaaiiy OeIN (19), inoaii?e o
a?aeiia?aeieo oiiaao iiaea ia?aoai?thaaoeny a oeiiaee aeey ?aaeoe?e o
na?aaeiaeu? A IN (13), nii??aeiaiee c caaaeueiei a na?aaeiaeuao A ? A
SN2 iiae?aiei IN ?aaeoe?e aaiceea?ii?ae?a c i-aooeeai?iii.

Oaeei /eiii, i?inoaaeo?oueny ooiaeaiaioaeueia ni?euei?noue SN2 iaoai?cia
?aaeoe?e aaici?eoei?eae?a (na?aaeiaeua A ?, /anoeiaa, A) oa
aaiceea?ii?ae?a (na?aaeiaeua A ? A). Ii?yae c oeei o iaeiiiey?ieo
?ic/eiieeao (na?aaeiaeua A) a?eue o?noue ?aaeoe?e aaici?eoei?eae?a c
ai?e?iaie ? N-CH3-ai?e?iaie a?aeaoaa?oueny ca o/anoth OeIN (19),
ooai?aiith yeeo ni?eythoue AAC a ?aaeoaioao, iecuee? oaiia?aoo?e,
iaeiiiey?i? ?ic/eiieee.

= (1/O – 1/303)103, ?iaeaen o0 oa?aeoa?eco? noaiaea?oio oaiia?aoo?o
(303 E). ?acoeueoaoii ?ic?aooieo aeaieo aaaaoioaeoi?iiai e?iaoe/iiai
aenia?eiaioo (27 aaee/ei kxyo) ca?aeii c ??aiyiiyi (21) ? ?aa?an?y (22).

(21)

(22)

R = 0.999, s0 = 0.0156 n/n0 = 27/27

) = 4-NH2 (-0.66), 4-OCH3 (-0.27), I (0).

= 0, oiaoi ?aae?cothoueny neiao?e/i? IN oeio (15), a?aeiia?aeii aoaeo?a
cai?niee?a Z o a?aeo?aei?e a?oi? oa oaiia?aoo?e.

+

,
(23)

R = 0.999, s0 = 0.022, n/n0 = 36/36

, r = 0.994 (24)

= -0.66 + 1.87 (1/O – 1/300) 103 , r = 0.980
(25)

?AAEOe?? A?I?EOEI?EAe?A C AI?E?IAIE A I?IOIAEOEAIEO ?IC*EIIEEAO

(oaae. 6).

, aea s0 a?aeiia?aea? noaiaea?oiiio ?ic/eiieeo (n = 5, Os = 0), aeey
?ioeo ?ic/eiiee?a Os = 0.24 (n = 3.5), -0.60 ( n = 7)]. O oaae. 7 ? 8
iaaaaeai? ?acoeueoaoe ia?iaee aeaieo aaaaoioaeoi?iiai e?iaoe/iiai
aenia?eiaioo o a?aeiia?aeiino? aei ??aiyiue (26) ? (27).

(26)

(27)

= 0.96).

= 0).

.

Oaaeeoey 5

Eiao?oe??ioe ??aiyiiy (6) aeey ?aaeoe?e aaici?eoei?eae?a c ai?e?iaie a
0.1, 2, 3.5, 5 ? 7 I ?ic/eiao OAN a OA i?e 25 0N

R

1 0.1 M 1.21 ( 0.05 2.56 ( 0.08 -0.31 ( 0.07 3.90 -8.25 0.999

2 2 M 1.15 ( 0.12 2.31 ( 0.06 0 – – 0.998

3 3,5 M -0.88 ( 0.09 1.84 ( 0.08 2.50 ( 0.15 0.361) 0.74 0.994

4 5 M 0.21 ( 0.06 1.05 ( 0.04 1.55 ( 0.12 -0.131) 0.671) 0.991

5 7M 1.15 (0.04 0.32 ( 0.03 0.54 ( 0.07 2.13 0.591) 0.998

_______________

1) Aenia?eiaioaeueii ?aae?ciaai? ?IO.

Oaaeeoey 6

aeey ?aaeoe?e aaici?eoei?eae?a c ai?e?iaie a ?ic/eiao OAN a OA i?e 25
0N

]

N 31) N 41)

N 51)

4-OMe -0.40 – -0.36 ( 0.06 4-OMe -0.51 -0.54

H 0 -0.88 ( 0.11 0.28 ( 0.01 3,5-Me2 -0.14 -0.46

3-Cl 0.37 0.07 ( 0.01 0.72 ( 0.03 H 0 -0.31

3-NO2 0.71 1.13 ( 0.14 1.45 ( 0.09 3-Cl 0.37 -0.27

5-NO2-3-CO2Me 0.96 1.61 ( 0.05 1.74 ( 0.02 3-NO2 0.71 0.10

[0.35] [-0.13]

[0.59]

________________

1) Iiia? ?aaeoe?eii? na??? a oaae. 5.

= 0.71).

= -0.88 ( 0.11 (3.5 I, Os = 0.24), 0.28 ( 0.01 (5 I , Os = 0), 1.13
( 0.02 (7 I, Os = -0.60).

Oaaeeoey 7

Eiao?oe??ioe ??aiyiiy (26) aeey ?aaeoe?e aaici?eoei?eae?a c ai?e?iaie a
?ic/eiao OAN a OA i?e 25 0N

-0.75 -0.75 -0.84 -0.87 –

Noi?niee aieea cai?niee?a O ? Y, a oaeiae na?aaeiaeua ia ?aaeoe?eio
caeaoi?noue nenoaie aaici?eoei?eaee – ai?e?ie iieno?oueny iie?e?i?eiith
?aa?an??th (28).

(28)

R = 0.987, s0 = 0.113, n/n0 = 46/49

On? eiao?oe??ioe ?aa?an?? (28) noaoenoe/ii cia/ou?. Ia aaee/eio kxys
ia?ao?anii aa??eiaai? oaeoi?e aieeaathoue ye nai? ii nia?, oae ? a on?o
ioaeeeaeo eiia?iaoe?yo ?o ia?ieo oa iio??eii? aca?iiae?e.

), a oaeiae ?icaeyioo? ?IO ?c no?oeoo?ith IN, aai ?? ci?iith.
Iani?aaae? aaee/eie ? ciaee oeeo ia?aiao??a aecia/athoueny iniaeeainoyie
nieueaaoaoe?eieo aoaeo?a OAN. Caaaeyee nai?i i?ioiiiaeiii?iei oa
i?ioiiiaeoeaioi?iei aeanoeainoyi OAN iiaea ooai?thaaoe c ?aaeoaioaie
anioe?aoe, ye? ca?eueoothoue [t-Bu(H)O…HNHAr, t-BuOH…ClCOAr,
t-BuOH…OC(Cl)Ar], aai ciaioothoue [t-BuOH…NH2Ar] oaeaee?noue i?ioeano.
Caaaeueiee aieea oeeo anioe?ao?a ia kxys ? eiiieaeniei.

Oaaeeoey 8

Eiao?oe??ioe ??aiyiiy (23) aeey ?aaeoe?e aaici?eoei?eae?a c ai?e?iaie a
?ic/eiao OAN i?e 25 0N

0.07 0.53 2.42 8.80

A?i caeaaeeoue ye a?ae eiioeaio?aoe?? OAN a OA, oae ? a?ae cai?niee?a O
a ai?e?iao. I?i oea na?ae/aoue a?ao?ee a eii?aeeiaoao kxys — n (?en. 5).

O aeiaaeeo ai?e?ia (a?ao?e a) ? 3-Nl-ai?e?ia (a?ao?e b) /?oei
i?inoaaeo?oueny ?ioaineaiee neia?a?ci aoaeo?a ci?oaiiai ?ic/eiieea.
?aaeoe?? a 2 I ?ic/ei? OAN a OA oa?aeoa?ecothoueny iaeneiaeueieie
aaee/eiaie kxys. Aeey ?aaeoe?e 3-i?o?iai?e?ia niinoa??aa?oueny e?eaa
iane/aiiy i?e n ( 2 (a?ao?e n), a aeey ?aaeoe?e iaeiaio
?aaeoe?eiicaeaoiiai 5-NO2-3-COOCH3-ai?e?ia caa??aa?oueny e?i?eia
caeaaei?noue kxys a?ae n (a?ao?e d) a onueiio ?ioa?aae? ci?ie
eiioeaio?aoe?? OAN.

) eiao?oe??io?a o ia?ao?anieo ei?aeyoe?yo ? iane?aeeii iacaaeainiaaieo
aoaeo?a niaoeeo?/ii? nieueaaoaoe??.

= 0.

Oaeei /eiii, aiane?aeie iacaaeainiaaieo aoaeo?a niaoeeo?/ii?
nieueaaoaoe?? ai?e?i?a o ?ic/eiao OAN a OA eiao?oe??ioe ia?ao?anieo
ei?aeyoe?e ia iiaeooue aooe aeei?enoai? ye iaoai?no?/i? e?eoa???
?icaeyiooeo ?aaeoe?e.

?AAEOe?? AAICA?Ae?EEA?II?Ae?A C A?EEAI?IAIE

= 0.08 ( 0.02 (IA), 0.17 ( 0.01 (IA:OA = 1:1), 0.24 ( 0.01 (IA:OA =
1:3) aeey ?aaeoe?e ca o/anoth AAA (Y = I) i?e 40 0N (oaae. 9).

H Ar
(

Ar – N ( ( ( C+ Br – (29)

H H Ar

Ar2 CH+ Br –
(

( (
(30)

Ar – NH ––H

, yeee oa?aeoa?eco? /ooeea?noue eii-ia?ieo i?ioean?a aei iiey?iino?
na?aaeiaeua [??aiyiiy (4)], a?ae cai?niee?a O a ai?e?iao (oaae. 10).
Noi?niee aieea oeeo oaeoi??a ia oaeaee?noue eii-ia?ieo ?aaeoe?e
iieno?oueny ianooiiei ??aiyiiyi ia?ao?anii? ei?aeyoe??:

lg kxii = -11.7 + (1.7(0.3)(o + (16.3(0.6)ps + (-3.5(0.7)(o ps ,
(31)

R = 0.998, s0 = 0.023, n = 12

Oaaeeoey 9

aeey eii-ia?ieo ?aaeoe?e AAA (cai?nieee Y) c a?eeai?iaie a IA oa eiai
noi?oao c OA i?e 40 0N

R

Ai?e?ie 4-CH3 IA 0.15 ( 0.07 0.950

IA:OA = 1:1 0.28 ( 0.02 0.997

IA:OA = 1:3 0.32 ( 0.04 0.980

3-NI3 IA 0.17 ( 0.01 0.999

I IA 0.08 ( 0.02 0.960

IA:OA = 1:1 0.17 ( 0.01 0.995

IA:OA = 1:3 0.24 ( 0.01 0.998

4,4(-(NI3)21) IA:OA = 1:3 0.47 ( 0.05 0.996

N-CH3-Ai?e?ie I IA 0.05 ( 0.01 0.999

N-Ph-Ai?e?ie I IA 0.05 ( 0.01 0.993

N,N-(CH3)2-Ai?e?ie I IA -0.96 ( 0.03 0.999

_________

1) (CH3C6H4)2CHCl

i?ae aieeaii AAC Y. Iayai?noue oaeiai aioeeiiiainaoe?eiiai aoaeoo,
i?eoaiaiiiai noaae?eiei i?ioeanai, aei yeeo iaeaaeaoue ?icaeyioo?
eii-ia?i? ?aaeoe??, i?aeoaa?aeaeo?oueny ?aa?an??th (32), c yei? aeo?ea?,
ui ?cie?iaoe/ia oaiia?aoo?a ia? oa?aeoa?ia aeey iueiai a?ae’?iia
cia/aiiy, T?ci= -323 E.

(32)

R = 0.999, s0 = 0.09, n = 34.

Oaaeeoey 10

[??aiyiiy (4)] aeey ?aaeoe?e AAA (cai?nieee Y) c ai?e?iaie
(cai?nieeeee O) a IA oa ia’?iieo noi?oao IA:OA (1:1, 1:3)

r

SN2-IP ?aaeoe??, 40 0N

I I 17.0 ( 0.6 0.999

3-Br 14.5 ( 1.0 0.998

3-NO2 13.2 ( 1.1 0.996

3,5-(NO2)2 11.8 ( 0.5 0.990

SN2 ?aaeoe??, 70 0N

3,3(-(NO2)2 4-NH2 (40 0C) 21.2 ( 1.7 0.997

4-NH2 21.8 ( 1.9 0.996

H 22.2 ( 1.1 0.999

3-NO2 23.0 ( 1.0 0.999

Oaeei /eiii, ia i?aenoaai? ia?ao?aniiai ei?aeyoe?eiiai aiae?co
a??ia?aei? ia?o?ooe eii-ia?ieo ?aaeoe?e AAA (RX) c ai?e?iaie (NuH)
iiaeooue aooe cia?aaeai? noaiith, ia ye?e iicia/ai? eeoa i?yi?
ia?aoai?aiiy.

NuH

RX ––––––––––––––––– R+X– ––––––––––––––– [ HNu …. R+X – ]( –––––––

NuH NuH NuH

RNu + HX

R+ X– (

( (

[ R – X …. HNu ]( –– [ R+X– …. HNu ]( –– Nu – H
––––––––––––––––––

AENIIAEE

1. O ?aaeoe?yo ioeeaio?eueiiai cai?uaiiy ca o/anoth aaici?eueieo,
aaiceeueieo oa aaica?ae?eeueieo noano?ao?a anoaiiaeaii caaaeueio
iaaaeeoeai?noue aoaeo?a aa??eiaaieo oaeoi??a (no?oeoo?a, na?aaeiaeua,
oaiia?aoo?a), e?euee?nii ioe?iaio ca aeiiiiiaith eiao?oe??io?a
ia?ao?anii? acaeiiae?? o a?aeiia?aeieo iie?e?i?eieo ?aa?an?yo, ye?
aaeaeaaoii iienothoue ?aaeoeai?noue aeine?aeaeaieo nenoai noano?ao –
ioeeaio?e.

2. Ciaeaeai? caeiiii??iino? noi?niiai aieeao aa??eiaaieo oaeoi??a ia
oaeaee?noue ioeeaio?eueiiai cai?uaiiy ? i?aenoaaith e?euee?niiai
i?aeoiaeo aei nenoaiaoecaoe?o oa ia?aaeaa/aiiy ?aaeoeaiino? c
o?aooaaiiyi ia?ao?anieo aca?iiae?e a aeoeaaoe?eiiio i?ioean?.

3. Caaaeyee aca?iiae?? aa??eiaaieo oaeoi??a ?aae?ciaaii yaeua
?ciia?aiao?e/iino?. Aia?oa io?eiaii aenia?eiaioaeuei? aeieace ?nioaaiiy
?ciia?aiao?e/ieo oi/ie ii ia?aiao?ao no?oeoo?e, na?aaeiaeua oa
oaiia?aoo?e o ?aaeoe?yo aaici?eaaeiaai?ae?a (YC6H4COL, L = Cl, Br),
aaiceea?ii?ae?a oa aaiceeaaicienoeueoiiao?a (YC6H4CH2L, L = Br,
OSO2C6H4Z) c ai?e?iaie (XC6H4NH2) a ??cieo ?ic/eiieeao (s) i?e ??cieo
oaiia?aoo?ao (O):

= 0 bs = 0

= 0 bs = 0

ao = 0

Cae?eniaii oi?eaeuei? a i?aai?/ieo ?aaeoe?yo ia?aoiaee /a?ac aeaye?
?ciia?aiao?e/i? oi/ee. I?e oeueiio niinoa??aa?oueny ?iaa?n?y
?aaeoeaiino? aeine?aeaeaieo noano?ao?a.

4. Ciaee eiao?oe??io?a ia?ieo aca?iiae?e i?ae no?oeoo?ieie oaeoi?aie
(cai?nieee X, Y ? Z) ocaiaeaeothoueny c ia?aaeaa/aieie ae?aa?aiith Ii?
I’Oa??aea-Aeaeaiena aeey SN2 i?ioean?a, ui aeaco? ia aiaeia?/iee
iaoai?ci aeine?aeaeaieo ?aaeoe?e.

5. ssaeua ?ciia?aiao?e/iino? a ?aaeoe?yo, ui i?ioiaeyoue a ai?ioiiieo
?ic/eiieeao, iia’ycaia c? ci?iith no?oeoo?e ia?ao?aeiiai noaio a iaaeao
ni?eueiiai aeey ia?ao?anii? ?aaeoe?eii? na??? SN2 iaoai?cia.
?ciia?aiao?e/i? oi/ee o?aeoothoueny ye e?euee?ni? ?iaeaene no?oeoo?e
ia?ao?aeieo noai?a, a eiao?oe??ioe ia?ieo aca?iiae?e – ye e?euee?nia
i??a ci?ie ?o no?oeoo?e.

6. ?ciia?aiao?e/i?noue o ?aaeoe?yo aaici?eoei?eae?a c ai?e?iaie a
noi?oao o?ao.-aooeeiaiai nie?oo c oei?aaicaiii ? iane?aeeii aeenaaeaino
aoaeo?a niaoeeo?/ii? nieueaaoaoe?? ai?e?i?a, ioaea aiia ia iiaea aooe
iia’ycaia c? ci?iith no?oeoo?e ia?ao?aeieo noai?a.

7. Iaoiae ia?ao?aniiai ei?aeyoe?eiiai aiae?co ? ia?niaeoeaiei noiniaii
io?eiaiiy aaaeeeai? ?ioi?iaoe?? i?i iaoai?cie ?aaeoe?e oa aeaoae?
no?oeoo?e ?o ia?ao?aeieo noai?a. Ai?iaaaeaeaiiy oeueiai iaoiaeo aeaei
ciiao c’ynoaaoe aiaeia??, iniaeeaino? oa a?aei?ii?noue iaoai?ci?a
ioeeaio?eueiiai cai?uaiiy ca o/anoth ??cieo ca i?e?iaeith
aeaeo?io?eueieo aoaeaoeaaeo oeaio??a:

a) aecia/aii oiiae oa iaae? ?aae?caoe?? ni?eueiiai aeey aaici?eueiiai,
aaiceeueiiai oa aaica?ae?eeueiiai noano?ao?a ocaiaeaeaiiai cai?uaiiy
(SN2 iaoai?ci);

a) iaa?oioiaaii iieiaeaiiy i?i aeaa oeie ia?ao?aeieo noai?a ?aaeoe?e
aaici?eoei?eae?a c a?eeai?iaie a iaaeao SN2 iaoai?cio: iiey?ieo o
i?o?iaaicai?, oei?aaicai? ? ?o noi?oao oa iaiiey?ieo oeeee?/ieo c
I-ca’yceii o noi?oao oei?aaicaio c oeeeeiaaenaiii;

a) iinooeueiaaii aeaa ia?o?ooe ioeeaio?eueiiai cai?uaiiy a
aaica?ae?eea?ii?aeao ca o/anoth aeo?aeiiai noano?aoo (SN2 iaoai?ci) ?
ooai?aii? aiane?aeie eiai eii?caoe?? u?eueii? eiiii? ia?e (SN2-IP
iaoai?ci) oa iaaiai?ai? oiiae ?o ?aae?caoe??;

a) io?eiaii aeai?, ye? na?ae/aoue i?i ooai?aiiy a eii-ia?ieo ?aaeoe?yo
oeeee?/ieo ia?ao?aeieo noai?a c I-ca’yceii i?ae ai?iia?oiith a?eeai?io
oa a?ii?ae-ai?iiii u?eueii? eiiii? ia?e aaica?ae?ee?e a?ii?aeo.

8. Aaaaoioaeoi?i? e?iaoe/i? aeine?aeaeaiiy ia?ao?anieo ?aaeoe?eieo na??e
ioeeaio?eueiiai cai?uaiiy nooo?ai ?anoe?ththoue ? iiaeeaeththoue
o?aaeeoe?ei? oyaeaiiy noiniaii ?o ?aaeoeaiino?, caaacia/othoue
iaoeiai-iaa?oioiaaia ieaioaaiiy iioeiaeueieo oiia cae?eniaiiy i?aeoe/ii
aaaeeeaeo i?ioean?a ia?aiin?a aaici?eueieo, aaiceeueieo ?
aaica?ae?eeueieo a?oii ca i?iaiiciaaieie iaoai?ciaie.

9. Caii/aoeiaaii iiaee iai?yiie o aeine?aeaeaii? iaoai?ci?a ?aaeoe?e
ioeeaio?eueiiai cai?uaiiy, iaoiaeieia?/iith iniiaith yeiai ? ia?ao?aniee
ei?aeyoe?eiee aiae?c ca’yce?a i?ae ei?aeueiaaieie aaee/eiaie.

NIENIE IIOAE?EIAAIEO I?AOeUe CA OAIITH AeENA?OAOe??

Oiaiueei E.A., Aii/a?ia A.I., Eeoaeiaiei E.I. Ia?ae?anoiia aeeyiea
caianoeoaeae ia nei?inoue ?aaeoeee a?ieeoei?eaeia n ia?ae/iuie
a?eeaieiaie a oei?aaiciea e ieo?iaaiciea // AEo?i.i?aai.oeiee. – 1977.
– O.13, aui.4. – N.761-766.

Acaeiiia aeeyiea yooaeoia no?oeoo?u a ?aaeoeeyo caiauaiiuo
aaiceea?iieaeia n ia?ae/iuie a?eeaieiaie / E.A.Oiaiueei, E.I.Eeoaeiaiei,
A.I.Ei?inoueaa, A.?.Oeoiie?iaa, I.I.Eo?aiiay // Aeiee. AI NNN?. – 1977.
– O.234, ? 6. – N.1358-1361.

Oiaiueei E.A., Eeoaeiaiei E.I., Aii/a?ia A.I. Eiee/anoaaiiue o/ao
ia?ae?anoiiai aeeyiey no?oeoo?u ia?ae/iuo a?eeaieiia e iiey?iinoe n?aaeu
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N.574-578.

Aii/a?ia A.I., Oiaiueei E.A., Eeoaeiaiei E.I. Ia?ae?anoiia aeeyiea
no?oeoo?e ?aaaaioia e iiey?iinoe n?aaeu a ?aaeoeeyo a?ieeoei?eaeia n
aieeeiii // AEo?i.i?aai.oeiee. – 1978. – O.14, aui.9. – N.1836-1841.

Ei?inoueaa A.I.., Eeoaeiaiei E.I., Oiaiueei E.A. Ia?ae?anoiia aeeyiea
yooaeoia no?oeoo?u e iiey?iinoe n?aaeu a ?aaeoeeyo aaiceea?iieaeia n
i-aooeeaieiii //Aeiee. AI NNN?. – 1978. – O. 242, ? 1. – N.121-124.

Aii/a?ia A.I., Oiaiueei E.A., Eeoaeiaiei E.I. Acaeiiaeaenoaea ia?ae/iuo
a?eeaieiia n aaicieeoei?eaeaie a ieceiiiey?iuo n?aaeao. Ia?ae?anoiay
ei??aeyoeey no?oeoo?a — n?aaea // AEo?i.i?aai.oeiee. – 1979. – O.15,
aui.8. – N.1654-1661.

Oiaiueei E.A., Aii/a?ia A.I., Eeoaeiaiei E.I. Acaeiiaeaenoaea
a?ieeoei?eaeia n 3-ooi?aieeeiii a n?aaeao ?acee/iie iiey?iinoe.
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1979. – O.15, aui.8. – N.1648-1654.

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E.A.Oiaiueei, E.I.Eeoaeiaiei, O.A.Aiaeeai? // AEo?i.i?aai.oeiee. –
1980. – O.16, aui.2. – N.347-352.

Ia?ae?anoiia aeeyiea iiey?iuo naienoa n?aaeu e no?oeoo?u noano?aoa a
?aaeoeeyo a?ieeoei?eaeia n N-iaoeeaieeeiaie / E.B.Oiaiueei,
E.I.Eeoaeiaiei, A.I.Aii/a?ia, I.E.Ei?aeeeiaa // AEo?i.i?aai.oeiee. –
1981. – O.17, aui.5. – N.965-971.

10. Eeoaeiaiei E.I., Oiaiueei E.A., Ei?inoueaa A.I. Acaeiiia aeeyiea
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with anilines in dioxane and its mixtures with dimethylsulfoxide. An
experimental verification // Organic Reactivity. – 1997. – Vol. 31, ?
1. – P. 177-180.

32. Oiaiueei E.A. Niiinoaaeaiea ?aaeoeeiiiie niiniaiinoe eieaeacieia e
ie?eaeeiia a ?aaeoeeyo n aaiceea?iieaeaie // Oai?ao. e yenia?ei. oeiey.
– 1997. – O. 33, ? 6. – N. 377-380.

Oiaiueei ?.A. Ia?ao?aniee ei?aeyoe?eiee aiae?c ?aaeoe?e ioeeaio?eueiiai
cai?uaiiy. ssaeua ?ciia?aiao?e/iino? oa no?oeoo?a ia?ao?aeieo noai?a. –
?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy aeieoi?a o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.03 – i?aai?/ia o?i?y. – ?inoeooo
o?ceei-i?aaie/ii? o?i?? oa aoaeao?i?? ?i. E.I.Eeoaeiaiea IAI Oe?a?ie,
Aeiiaoeuee, 1998.

Aeena?oaoe?th i?enay/aii ieoaiiyi ia?ao?aniiai ei?aeyoe?eiiai aiae?co
?aaeoe?e ioeeaio?eueiiai cai?uaiiy ca o/anoth aaici?eueieo, aaiceeueieo
oa aaica?ae?eeueieo noano?ao?a. A aeena?oaoe?? caii/aoeiaaii iiaee
iai?yiie o aeine?aeaeaii? iaoai?ci?a oeeo ?aaeoe?e. A?i a?oioo?oueny ia
aaaaoioaeoi?iiio aiae?c? ca’yce?a i?ae ?aaeoeai?noth nenoai noano?ao –
ioeeaio?e ? no?oeoo?ith ?aaeoaio?a, aeanoeainoyie na?aaeiaeua oa
oaiia?aoo?ith. Ia i?aenoaa? aaaaoioaeoi?ieo e?iaoe/ieo aenia?eiaio?a
io?eiaii /eneaii? aeieace oi?eaeueiiai yaeua ?ciia?aiao?e/iino?.
Ai?iaaaeaeaii iaoiaeieia?th aeei?enoaiiy eiao?oe??io?a ia?ao?anii?
aca?iiae?? oa ?ciia?aiao?e/ieo oi/ie ye e?euee?nieo ?iaeaen?a iaoai?ci?a
?aaeoe?e ? no?oeoo?e ?o ia?ao?aeieo noai?a. ?acoeueoaoe ?iaioe iathoue
cia/aiiy aeey aeine?aeaeaiiy iaoai?ci?a ?aaeoe?e oa ?ic?iaee e?euee?nii?
oai??? ?aaeoe?eii? caeaoiino?.

Eeth/ia? neiaa: ia?ao?aniee ei?aeyoe?eiee aiae?c, ioeeaio?eueia
cai?uaiiy, iaoai?ci, ?ciia?aiao?e/i?noue, eiao?oe??ioe ia?ao?anii?
aca?iiae??, no?oeoo?a ia?ao?aeiiai noaio.

Oiaiueei E.A. Ia?ae?anoiue ei??aeyoeeiiiue aiaeec ?aaeoeee
ioeeaioeeueiiai caiauaiey. ssaeaiea eciia?aiao?e/iinoe e no?oeoo?a
ia?aoiaeiuo ninoiyiee. – ?oeiienue.

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie aeieoi?a oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.03 – i?aaie/aneay oeiey. — Einoeooo
oeceei-i?aaie/aneie oeiee e oaeaoeiee ei. E.I.Eeoaeiaiei IAI Oe?aeiu,
Aeiiaoee, 1998.

Aeenna?oaoeey iinayuaia aii?inai ia?ae?anoiiai ei??aeyoeeiiiiai aiaeeca
?aaeoeee ioeeaioeeueiiai caiauaiey n o/anoeai aaicieeueiuo, aaiceeueiuo
e aaicaeae?eeueiuo noano?aoia. A aeenna?oaoeee iieiaeaii ia/aei iiaiio
iai?aaeaieth a enneaaeiaaiee iaoaieciia yoeo ?aaeoeee, aace?othueony ia
iiiaioaeoi?iii aiaeeca i?e/eii-neaaenoaaiiuo naycae iaaeaeo ?aaeoeeiiiie
niiniaiinoueth nenoai noano?ao – ioeeaioee e no?oeoo?ie ?aaaaioia,
naienoaaie ?anoai?eoaeae e oaiia?aoo?ie. Ia iniiaaiee iiiaioaeoi?iuo
eeiaoe/aneeo yenia?eiaioia iieo/aiu iiiai/eneaiiua aeieacaoaeuenoaa
oieeaeueiiai yaeaiey eciia?aiao?e/iinoe. ?ac?aaioaia iaoiaeieiaey
eniieueciaaiey eiyooeoeeaioia ia?ae?anoiuo acaeiiaeaenoaee e
eciia?aiao?e/aneeo oi/ae a ea/anoaa eiee/anoaaiiuo eiaeaenia iaoaieciia
?aaeoeee e no?oeoo?u eo ia?aoiaeiuo ninoiyiee. ?acoeueoaou ?aaiou eiatho
cia/aiea a enneaaeiaaiee iaoaieciia ?aaeoeee, a oaeaea a ?ac?aaioea
eiee/anoaaiiie oai?ee ?aaeoeeiiiie niiniaiinoe.

Eeth/aaua neiaa: ia?ae?anoiue ei??aeyoeeiiiue aiaeec, ioeeaioeeueiia
caiauaiea, iaoaieci, eciia?aiao?e/iinoue, eiyooeoeeaiou ia?ae?anoiiai
acaeiiaeaenoaey, no?oeoo?a ia?aoiaeiiai ninoiyiey.

Shpanko I.V. Cross-correlation analysis of nucleophilic substitution
reactions. Isoparametricity phenomenon and transition state structure. –
Manuscript.

Thesis for a doctor’s degree by speciality 02.00.03 – organic chemistry.
– L.M.Litvinenko Institute of Physical Organic and Coal Chemistry of
National Academy of Sciences of Ukraine, Donetsk, 1998.

The dissertation is devoted to design frontier topics that are connected
with cross-correlation analysis of the nucleophilic substitution
reactions of benzoyl, benzyl and benzhydryl substrates. A new derection
in the study of the mechanisms of these reactions is elaborated which
based on the polifactorial analysis of cause-effect relationships
between reactivity and reagent structures, solvent properties and
temperatures. On the strength of multifactorial kinetic experimentations
the numerous evidences for the existance of the unique isoparametricity
phenomenon has been obtained. The methodology of the application of
cross-interaction coefficients and isoparametrical points as
quantitative indexes of reaction mechanisms and transition state
structures was developed. The results of the work are significant for
development of novel trends in the study of reaction mechanisms and
organic reactivity.

Key words: cross-correlation analysis, nucleophilic substitution,
mechanism, isoparametricity, cross-interaction coefficients, transition
state structures.

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