Синтез, реакційна здатність та спектральні властивості похідних імінокумарину: Автореф. дис… канд. хім. наук / О.О. Карасьов, Харк. держ. ун-т. — Х.

OA?E?ANUeEEE AeA?AEAAIEE OI?AA?NEOAO

EA?ANUeIA

IEAENAIAe? IEAEN?EIAE*

OAeE 547.814+541.127+542.938

NEIOAC, ?AAEOe?EIA CAeAOI?NOUe OA NIAEO?AEUeI? AEANOEAINO? IIO?AeIEO
?I?IIEOIA?EIO

02.00.03 — i?aai?/ia o?i?y

AAOI?AOA?AO

aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy

eaiaeeaeaoa o?i?/ieo iaoe

OA?E?A — 1999

Aeena?oaoe??th ? ?oeiien.

?iaioo aeeiiaii o a?aeae?e? o?ceei-i?aai?/ii? o?i?? Iaoeiai-aeine?aeiiai
?inoeoooo o?i?? i?e Oa?e?anueeiio aea?aeaaiiio oi?aa?neoao?.

IAOEIAEE EA??AIEE:eaiaeeaeao o?i?/ieo iaoe, no. iaoe. ni?a?ia?oiee,

Aei?ioaiei Aiae??e Ieaaiae/,

caa. a?aeae?eii o?ceei-i?aai?/ii? o?i?? IAe? o?i?? i?e Oa?e?anueeiio
aea?aeaaiiio oi?aa?neoao?, i. Oa?e?aIOEOe?EI? IIIIAIOE:aeieoi? o?i?/ieo
iaoe, aeioeaio,

Aeanaiei Na?a?e Ieoaeeiae/,

aeioeaio eaoaae?e i?aai?/ii? o?i??

Oa?e?anueeiai aea?aeaaiiai oi?aa?neoaoo, i. Oa?e?a.

eaiaeeaeao o?i?/ieo iaoe, no. iaoe. ni?a?ia?oiee,

ss?aiaiei Oaae?? Aai?a?eiae/,

caa. eaai?aoi???th, Oe?IAe? oa?iaeioa?ai?? aiaeie?eiieo caoai?thaaiue
IIC Oe?a?ie, i. Oa?e?aI?IA?AeIA ONOAIIAA:Ee?anueeee aea?aeaaiee
oi?aa?neoao ?i.Oa?ana Oaa/aiea (eaoaae?a i?aai?/ii? o?i??), i. Ee?a,
i?i?noa?noai ina?oe Oe?a?ie

Caoeno a?aeaoaeaoueny «_22_» ea?oiy 1999 ?. i 17 aiae. ia can?aeaii?
niaoe?ae?ciaaii? a/aii? ?aaee Ae 64.051.14 Oa?e?anueeiai aea?aeaaiiai
oi?aa?neoaoo. (Oe?a?ia, 310077, i. Oa?e?a, iaeae. Naiaiaee, 4, aoae.
7-80)

C aeena?oaoe??th iiaeia iciaeiieoeny a Oeaio?aeuei?e iaoeia?e
a?ae?ioaoe? Oa?e?anueeiai aea?aeaaiiai oi?aa?neoaoo.

Aaoi?aoa?ao ?ic?neaii «_22_» aa?aciy 1999 ?.

A/aiee nae?aoa?

niaoe?ae?ciaaii? a/aii? ?aaee,

eaiaeeaeao o?i?/ieo iaoe, aeioeaio Eia?iiaa E.I.

CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE

Aeooaeuei?noue oaie iaoiiaeaia aaaeeea?noth i?iaeaie iiooeo i?aai?/ieo
niieoe c aenieeie eaaioiaeie aeoiaeaie oeoi?anoeaioe??, ui
canoiniaothoueny a ??cieo aaeocyo iaoee oa oaoi?ee: a aeoeaieo
na?aaeiaeuao eaca??a ia i?aai?/ieo aa?aieeao, o yeino? iioe/ieo
a?aea?ethaa/?a oa ethi?ianoeaioieo aeiaeaoe?a o ??ciiiai?oieo
caaa?aethth/eo eiiiiceoe?yo, a oaeiae a yeino? oeoi?anoeaioieo ciiae?a
oa i?oie a a?ieia?? oa iaaeeoeei?. O oeueiio ca’yceo oe?eani?yiiaaiee
iiooe iiaeo aoaeoeaieo ethi?iioi??a iio?aao? anoaiiaeaiiy aca?iica’yceo
no?oeoo?e oa niaeo?aeueii-ethi?ianoeaioieo aeanoeainoae, a oiio /ene? ia
aac? aaea a?aeiieo niieoe.

O ?iaio? aeine?aeaeo?oueny eean ?i?iieoia?ei?a oa ?o ni?yaeaieo eeneio –
nieae 2-ai?ii-1-aaicii??ee?th, ye? ?ai?oa nenoaiaoe/ii ia aea/aeeny,
iacaaaeath/e ia oa, ui na?aae ?i?iieoia?ei?a aoei ciaeaeaii niieoee c
aenieeie eaaioiaeie aeoiaeaie ethi?ianoeaioe?? ye a i?aai?/ieo
?ic/eiieeao, oae ? o aiae?.

Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie. Aeena?oaoe?eia
?iaioa ? neeaaeiaith /anoeiith ieaiiaeo aeine?aeaeaiue, ni?yiiaaieo ia
anoaiiaeaiiy aca?iica’yceo i?ae no?oeoo?ith i?aai?/ieo ethi?iioi??a oa
?o niaeo?aeueii-ethi?ianoeaioieie aeanoeainoyie, ye? i?iaiaeeeenue
i?ioyaii ?yaeo ?ie?a a IAe? o?i?? Oa?e?anueeiai aea?aeoi?aa?neoaoo a
?aieao ainiaeiaia??ii? IAe? «Neioac oa o?ceei-o?i?/i? aeine?aeaeaiiy
oioino?eeeo ethi?iioi??a — iio?aeieo eoia?eio, ea?ainoe?eeo,
?ciea?ainoe?eeo oa ia?niaeoeaa ?o aeei?enoaiiy a eaca?i?e oaoi?oe?» oa
aea?aeathaeaeaoieo IAe? «?ioi?iaoe?eia nenoaia ca aeanoeainoyie
i?aai?/ieo ethi?iioi??a oa eaca?ieo aa?aiee?a», ? aea?ae?a?no?aoe??
0194U021414 ? «Oioii?ea oa i?aeiieaeoey?i? aca?iiae?? i?aaiiethi?iioi??a
?iiii? aoaeiae», ? aea?ae?a?no?aoe?? 0197U002449.

Iaoa ?iaioe — neioac iio?aeieo ?i?iieoia?eio oa anoaiiaeaiiy
e?euee?niiai aca?iica’yceo i?ae ?o aoaeiaith oa o?ceei-o?i?/ieie
oa?aeoa?enoeeaie aeey noai?aiiy iiaeo eaca?ieo aa?aiee?a ia iniia?
niieoe oeueiai eeano.

Aeey aeinyaiaiiy aeaii? iaoe aoei iaiao?aeiei:

— neioacoaaoe nenoaiaoe/i? ?yaee 3-ai?iiea?aii?e- oa
3-(2-aaicei?aeacie?e)?i?iieoia?ei?a, a oaeiae i?iaeoeo?a ?o aca?iiae?? c
eeneioaie oa aiaeith;

— onoaiiaeoe ei?aeyoe?? ?aaeoe?eii? caeaoiino? oa niaeo?aeueieo
aeanoeainoae iaea?aeaieo niieoe ?c no?oeoo?ieie ia?aiao?aie ?o iieaeoe.

Aenia?eiaioaeuei? iaoiaee. Aeey i?iaaaeaiiy oeueiai aeine?aeaeaiiy aoei
caeo/aii iaoiaee ?aioaaiino?oeoo?iiai aiae?co, II?, ?* niaeo?ineii??,
aeaeo?iiii? aani?aoe?eii? oa oeoi?anoeaioii? niaeo?ineii??, eaca?e ia
aa?aieeao c iaea/eith oeao-eaiiith oa aeneia?iei eaca?ii,
eaaioiaio?i?/i? ?ic?aooiee a ?aieao iai?aaii??e/ieo iaoiae?a AI1 oa ?I3,
a oaeiae ?ic?aooiee o p-aeaeo?iiiiio iaaeeaeaii? Ia??a-Ia?eca?a-Iiiea.

Iaoeiaa iiaecia ?iaioe.

— Neioaciaaii iio?aei? 3-ai?iiea?aii?e- oa
3-(2-aaicei?aeacie?e)?i?iieoia?eio ? eoia?eio, a oaeiae nie?
2-ai?ii-1-aaicii??ee?th ? 2-(3-eoia?ei?e)aaicei?aeacie?th — anueiai 50
niieoe, ?c ieo 29 — aia?oa. Ia i?aenoaa? aeine?aeaeaiiy aaia?aoe?eii?
caeaoiino? 4 niieoee cai?iiiiiaaii aeey aeei?enoaiiy a yeino? eaca?ieo
aa?aiee?a o ??aeeiieo eaca?ao.

— Cai?iiiiiaaii iaeiinoaae?eiee iaoiae neioaco nieae
2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th, canoinoaaiiy yeiai
i?ecaiaeeoue aei nooo?aiai ca?eueoaiiy aeoiae?a niieoe c aeiii?ieie
cai?nieeaie.

— Aeyaeaii oa e?euee?nii ioa?aeoa?eciaaii oaooiia??th
7-a?ae?iene?i?iieoia?ei?a o noi?oao aoaiie — aiaea oa aoeaoii?o?ee —
aiaea.

— Aia?oa e?euee?nii ioa?aeoa?eciaaii niaeo?aeueii-ethi?ianoeaioi?,
eeneioii-iniiai? aeanoeaino? oa ?aaeoe?eio caeaoi?noue nieae
2-ai?ii-1-aaicii??ee?th. Anoaiiaeaii ei?aeyoe?? oeeo aeanoeainoae a?ae
aeaeo?iiiiai aieeao cai?niee?a, i?iaaaeaii aiae?c o?ce/iiai ci?noo
iaea?aeaieo caeaaeiinoae..

— Ia i?aenoaa? anoaiiaeaieo ei?aeyoe?e no?oeoo?e, ?aaeoe?eii? caeaoiino?
oa niaeo?aeueieo aeanoeainoae aeine?aeaeaieo niieoe aecia/aii +-
eiinoaioo aeey ij-eiiaeainiaaiiai 2,3,4,6,7,8-aaenaa?ae?io?iie?cei?eo a
ia?a-iieiaeaii?, yeee ia? iaea?eueoo aeaeo?iiiaeiii?io caeaoi?noue
na?aae a?aeiieo iaca?yaeaeaieo cai?niee?a.

I?aeoe/ia oe?ii?noue ?iaioe. Neioaciaaii 4 iiaeo eaca?ieo aa?aieee aeey
aeei?enoaiiy o eaca?ao c eaiiiaith oa eaca?iith (XeCl*) iaea/eith.
Oaooiia??y 7-a?ae?iene?i?iieoia?ei?a o aiaeii-i?aai?/ieo na?aaeiaeuao,
yea oa?aeoa?eco?oueny ci?iaie ye o iieiaeaii? aeiaaioaeeueiai? nioae
iiaeeiaiiy
(picscalex85010009000003b10000000200170000000000050000000902000000000400
000002010100050000000102ffffff00040000002e011800050000003102010000000500
00000b0200000000050000000c02a00160011200000026060f001a00ffffffff00001000
0000c0ffffffe0ffffff20010000800100000b00000026060f000c004d61746854797065
0000300017000000fb0280fe0000000000009001000000cc0002001054696d6573204e65
7720526f6d616e2043797200ccdd040000002d01000009000000320ad200400001000000
7e00cf0010000000fb0280fe0000000000009001000000020002001053796d626f6c0002
040000002d01010004000000f001000009000000320a40014d00010000006e00cb000a00
000026060f000a00ffffffff01000000000010000000fb021000070000000000bc020000
00cc0102022253797374656d00cc040000002d01000004000000f0010100030000000000
= 4000 5000 ni–1), oae ? o eaaioiaiio aeoiae? oeoi?anoeaioe?? ( 0.6),
aeicaiey? ?aeiiaiaeoaaoe oe? niieoee aeey e?euee?niiai aecia/aiiy aiaee
a i?aai?/ieo ?ic/eiieeao, a oaeiae o yeino? oeoi?anoeaioieo ciiae?a a
iaaeeei-a?ieia?/ieo aeine?aeaeaiiyo. 7-Ae?aoeeai?ii- oa
7-(2,3,4,6,7,8-aaenaaeae?io?iie?cei?e)?i?iieoia?eie iiaeooue aooe
aeei?enoai? ye oeoi?anoeaioi? ?iaeeeaoi?e a ae?aiacii? 4.5 – 7.5 iae.
?I.

Iniaenoee aianie aaoi?a iieyaa? a o/ano? a iinoaiiaoe? caaea/
aeine?aeaeaiiy, i?iaaaeaii? neioaoe/ieo aenia?eiaio?a, ?ic?iaoe? iiaiai
iaoiaeo neioaco nieae 2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th,
aei??thaaii? oa ?ioa?i?aoaoe?? OO oa ?* niaeo??a iaea?aeaieo niieoe,
i?iaaaeaii? eaaioiaio?i?/ieo ?ic?aooie?a, iaoaiaoe/i?e ia?iaoe? oa
ocaaaeueiaii? iaea?aeaieo ?acoeueoao?a, a oaeiae o oi?ioethaaii?
aeniiae?a.

Aaoi? aeneiaeth? iiaeyeo I.?.?oaoeiao oa E.E.Eoeaoeuee?e ca i?iaaaeaiiy
aei???a ANI ? oeoi?anoeaioieo oa?aeoa?enoee, aecia/aiiy eiinoaio
??aiiaaa ? nei?inoae a?ae?ie?co, N.I.ss?iieaiei ca o/anoue o iinoaiiaoe?
caaea/ oa iaaiai?aii? ia?aeiieo ?acoeueoao?a ?iaioe,, A.A.Oiainueeiio ca
iaaeaiiy i?ia?aie eaaioiaio?i?/ieo ?ic?aooie?a «EASY PIE» oa ??
ei?aeooaaiiy ca i?ioaiiyi aaoi?a, A.I.Aaoia?o ca i?iaaaeaiiy
?aioaaiino?oeoo?iiai aiae?co, I.A.Niaieiith ? A.A. Oa?eianueeiio ca
aei??thaaiiy aaia?aoe?eieo oa?aeoa?enoee, I.N.I?aiaiei ca i?iaaaeaiiy
aei???a II? niaeo??a.

Ioae?eaoe?? oa ai?iaaoe?y ?iaioe. Iniiai? ?acoeueoaoe ?iaioe
iioae?eiaaii o 4 noaooyo oa 1 aaoi?nueeiio na?aeioeoa? ia aeiao?ae. Ca
?acoeueoaoaie aeine?aeaeaiue c?iaeaii aeiiia?ae? ia V Ananithci?e
eiioa?aioe?? «I?aai?/i? ethi?iioi?e oa ?o canoinoaaiiy o ia?iaeiiio
ainiiaea?noa?» (Oa?e?a, 1987 ?.), I?aeia?iaei?e eiioa?aioe?? c
ethi?ianoeaioe?? (Iineaa, 22-24 eenoiiaaea 1994 ?.), I?aeia?iaeiiio
nai?ia?? c i?aeiieaeoey?ii? aca?iiae?? oa eiioi?iaoe?yi iieaeoe (Oa?e?a,
3-8 aeiaoiy 1994 ?.), XXVII Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??
(Oa?e?a, eenoiiaae 1995 ?.), Oe?a?inueei? eiioa?aioe?? «O?i?y
acioai?nieo aaoa?ioeeee?a» (Oa?e?a, 1-3 aeiaoiy 1997 ?.).

No?oeoo?a oa ianya aeena?oaoe??. Aeena?oaoe?eia ?iaioa neeaaea?oueny ?c
anooio, i’yoe ?icae?e?a, aeniiae?a, nieneo aeei?enoaieo e?oa?aoo?ieo
aeaea?ae ?c 163 iaeiaioaaiue. Ianya aeena?oaoe?? noaiiaeoue 109
noi??iie, aeeth/ath/e 17 ?enoie?a oa 21 oaaeeoeth.

IA’?EOE AeINE?AeAEAIIss

Aea?? ia’?eo?a aeine?aeaeaiiy aoei i?iaaaeaii o ?aieao iiooeo niieoe,
ye? iathoue ?ioaineaio ethi?ianoeaioe?th o ?ic/eiao aeey aeei?enoaiiy ?o
a aeoeaieo na?aaeiaeuao ??aeeiieo eaca??a oa ioe?iee ia?niaeoea
canoinoaaiiy aeey oeueiai iio?aeieo ?i?iieoia?eio. Iaie aoei ia?aii oae?
niieoee:

Ia i?eeeaae? niieoee VII iieacaii ioia?aoe?th aoii?a 1-aaicii??aiiaiai
oeeeeo.

Aeey ioe?iee aieeao aeoeaioi?ii? caeaoiino? cai?nieea o iieiaeaii? 3 oa
aieeao iaoeethaaiiy ai?iia?oie ia no?ee?noue nieae
2-ai?ii-1-aaicii??ee?th aei a?ae?ie?co, aoei oaeiae neioaciaaii oae?
niieoee:

INIIAIEE CI?NO ?IAIOE.

Iaoiaee neioaco, no?oeoo?a oa ?aaeoe?? iio?aeieo ?i?iieoia?eio

A e?oiaeyae? i?eaiaeyoueny a?aeii? iaoiaee neioaco ?i?iieoia?ei?a oa
nieae 2-ai?ii-1-aaicii??ee?th, ?o ?aaeoe?? c aeaeo?io?eaie oa
ioeeaio?eaie. Ia i?aenoaa? iaaaaeaieo aeaieo iieacaii, ui aeey
aeine?aeaeaiiy iaoai?ci?a ?aaeoe?e oeeo niieoe ? iaiao?aeiei o?aooaaiiy
?o eeneioii-iniiaieo aeanoeainoae.

Neioac oa aoaeiaa ?i?iieoia?ei?a oa nieae 2-ai?ii-1-aaicii??ee?th

Neioac ia?oei?ao?a 2-ai?ii-3-ai?iiea?aii?e-1-aaicii??ee?th (Ia-a)
cae?eniaii aca?iiae??th iio?aeieo nae?oeeeiaiai aeueaeaa?aeo c
oe?aiiaoeaoai?aeii c ooai?aiiyi 3-ai?iiea?aii?e?i?iieoia?ei?a (IVa-a) ?
ia?iaeith inoaii?o 70%-iith HClO4 :

Aeoiaee ?i?iieoia?ei?a, iaea?aeaieo ca oe??th ?aaeoe??th, neeaaeathoue
15 – 85%. Aeey neioaco ia?oei?ao?a
2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th aoei cai?iiiiiaaii
i?ea?iaeueio iaoiaeeeo — aca?iiae?th iio?aeieo nae?oeeeiaiai
aeueaeaa?aeo c ia?oei?aoii (aai oei?eaeii)
2-oe?aiiiaoeeaaicei?aeacie?th:

Aeei?enoaiiy oe??? iaoiaeeee i?ecaiaeeoue aei nooo?aiai ca?eueoaiiy
aeoiaeo ( 70%) nieae 2-ai?ii-1-aaicii??ee?th.

Nie? 2-iaoeeai?ii-1-aaicii??ee?th aoei iaea?aeaii ia?aai?ithaaiiyi
3-ai?iiea?aii?e?i?iieoia?eio oa nieae
3-(2-aaicei?aeacie?e)-7-R-1-aaicii??ee?th i?e aca?iiae?? c
a?ae?ioei?eaeii iaoeeai?io.

A ?* niaeo?ao ?i?iieoia?ei?a (IV,V), a oaaeaoeao KBr, aeyaeaii nioao
aaeaioieo eieeaaiue ca’yceo N=N (1644-1686 ni–1). Oaeiae, a iaeano?
2800-3200 ni–1 niinoa??aa?oueny oe?iea no?oeoo?iaaia nioaa eieeaaiue
anioe?eiaaii? a?oie N-H aaicei?aeacieo. I?e oeueiio ciaeaeaii eeoa
neaaea iiaeeiaiiy, iaoiiaeaia aaeaioieie eieeaaiiyie ca’yce?a N-H
?i?iia?oie (3100-3400 ni–1). A ?* niaeo?ao nieae 2-ai?ii-1-aaicii??ee?th
(I,II,VIII-XI) aeyaeaii «?iii??ao» nioao ca?aaeiuei? ?ioaineaiino? i?e
1663-1686 ni–1 oa ?ioaineaio nioao iiaeeiaiiy ia?oei?ao-?iio i?e 1100
ni–1. A ?* niaeo?ao eoia?ei?a (VI,VII) aeyaeaii ?ioaineaio nioao
ea?aii?eueii? a?oie (1690-1710 ni–1) oa nioao aaeaioieo eieeaaiue
iiey?eciaaiiai iiaea?eiiai ca’yceo (1550-1600 ni–1). O aeniei/anoioi?e
iaeano? ciaeaeaii iioe?aio nioao aaeaioieo eieeaaiue ca’yceo N-H a
iaeano? 3320-3350 ni–1.

I?e i?iaaaeaii? neioaco nieae
2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th iaie aoei anoaiiaeaii, ui
niieoea IIae a caeaaeiino? a?ae niiniao neioaco iiaea aooe aeae?eaia o
aeaeyae? e?enoae?a c a?ae??ciyth/eieny o?ce/ieie aeanoeainoyie, oiae? ye
II?, OO niaeo?e oa niaeo?e oeoi?anoeaioe?? ?o ?ic/ei?a aeyaeeenue
?aeaioe/ieie. I?e ia?ae?enoae?caoe?? ?a/iaeie IIae-1 ?c i?iiaiieo-2 aoei
iaea?aeaii e?enoaee, ?aeaioe/i? oi?i? IIae-2.

Oaaeeoey 1

O?ce/i? aeanoeaino? niieoe IIae, neioaciaaieo ??cieie iaoiaeaie.

?Iaoiae neioacoAeo?aeO.ie.,N, ni–1 (e)?* a EAr, wmetafile8?
??±???????????? ???????????yyy????.????1??????
???????  `???&??yyyy?????Ayyyayyy ????? ???&?
?MathType??0????u?th??????(62500)3100-34007.2-7.6 (i., a?ii.), 8.65
(n., H4)IIae-2A7027920000

(62500)32607.2-7.6 (i., a?ii.), 8.65 (n., H4)Aeey c’ynoaaiiy i?e/ei
icia/aieo a?aei?iiinoae aoei i?iaaaeaii ?aioaaiino?oeoo?ia
aeine?aeaeaiiy c?ace?a iaio aeae?a e?enoae?a. Aoei anoaiiaeaii, ui
iieaeoea ?i?iieoia?eio a e?enoae? IIae-2 ? i?ioiiiaaiith, a e?enoae
IIae-1 yaey? niaith noia?iiceoe?th i?ioiiiaaii? oa iai?ioiiiaaii?
iieaeoe. Aoii N(1) aeyaey?oueny ?acoii?yaeaeaiei ca aeaiia
??aiieiia??ieie iiceoe?yie; ?io? aaiiao?e/i? oa?aeoa?enoeee

iieaeoe a iaio no?oeoo?ao ? aeecueeeie. O no?oeoo?? IIae-2 ai?iiii ?
cae/aeiee ia?oei?ao-?ii c a?aenoaiyie Cl–O a?ae 1.402(6) aei 1.438(5) A
oa aaeaioieie eooaie a?ae 108.0(3) aei 112.3(3). A no?oeoo?? IIae-1
ai?ii ia? a?eueo neeaaeio aoaeiao. A?i i?noeoue aeaa ia?oei?ao-?iie,
i?ae yeeie ciaoiaeeoueny i?ioii. Aeinoaoiuei iaea a?aenoaiue O(2)–O(6) —
2.875 A aeaco? ia iayai?noue o?ueiooeaio?iaiai aiaeiaaiai ca’yceo
O(2)···I···O(6). Oaeei /eiii, ai?iiii o no?oeoo?? IIae-1 aenooia?
a?ae?iaeeia?oei?ao-?ii [H(ClO4)2]–, ooai?aiiy yeiai o e?enoaeao ?ai?o ia
niinoa??aaeiny.

?en. 1. Iaeeaaeaiiy i?ioiiiaaii? oa iaeo?aeueii? iieaeoe o e?enoae?
IIae-1. O o?aaiaio? N1-N1-I1N1 aa?oi? cia/aiiy a?aeiia?aeathoue
i?ioiiiaai?e oi?i?, ieaei? — iaeo?aeuei?e.

I?ioiioaaiiy iieaeoee ii ?i?iia?oi? i?ecaiaeeoue aei oaeiaaeaiiy ca’yceo
C(1)-N(1), ui aeaco? ia ci?io ?? e?aoiino?, a oaeiae ia ci?io aeiaaeeie
ca’yce?a o i??aiiaiio aaoa?ioeeee?, ia yeiio eieae?ciaaii ca?yae
i?ioiiiaaii? iieaeoee: ca’ycie C(2)-C(3) noa? aeiaoei, a ca’ycie
O(1)-C(1) — i?ei?oii ei?iooei, ai?ae o iieaeoe?
3-(2-aaicei?aeacie?e)-7-ae?aoeeai?iieoia?eio. A iaio no?oeoo?ao
niinoa??aa?oueny aioo??oiueiiieaeoey?iee aiaeiaaee ca’ycie
H(1,N1)···N(4), ui c’?aeio? aaicei?aeacieueiee oa aaicii??aiiaee
o?aaiaioe, oa i?ecaiaeeoue aei cia/iiai nieiuaiiy iieaeoee.

Aeine?aeaeaiiy ?aaeoe?eii? caeaoiino? iio?aeieo ?i?iieoia?eio

Nie? I-III aeia?a ?ic/eiythoueny o iiey?ieo ai?ioiiieo ?ic/eiieeao,
nie?oao oa aiaeii-nie?oiaeo noi?oao. Aeey aea/aiiy i?ioie?oe/ieo
??aiiaaa oa ?aaeoe?? a?ae?ie?co aeine?aeaeoaaieo niieoe aoei aea?aii a
yeino? noaiaea?oiiai ?ic/eiieea noi?o aiaea-aoaiie, yea i?noeoue 42.43%
aoaiieo (50% ia. i?e 20N). Aea?? oe??? nenoaie iaoiiaeaiee aeinoaoiuei
aeia?ith ?ic/eii?noth aeine?aeaeoaaieo niieoe, a oaeiae oei, ui a
iiae?aieo

nenoaiao aecia/aiiy ?I na?aaeiaeua ? iiaeeeaei c aeinoaoi?i nooiaiai
aeinoia??iino? iaoiaeii iioaioe?iiao??? ?c neeyiei aeaeo?iaeii.

Oaaeeoey 2

Cia/aiiy a?ae’?iieo eiaa?eoi?a eiinoaio eeneioii? aeennioe?aoe??
iiiieao?ii?a (I) — pK1, iiiieao?ii?a (II) — pK1, iiiieao?ii?a (III) —
pK3 oa aeeeao?ii?a (II2+) — pK2 a 50 ia.% aoaiie? i?e 20 N.

?K
iRIIIIIIII2+H(a)4.930.015.310.023.200.01(–0.21)7–OCH3(a)5.290.015.760.01
3.600.03(–0.04)7–OH(a)5.570.016.120.023.690.01(0.10)7–Et2N(a)6.840.027.1
50.014.320.010.500.027–Quin.(ae)7.500.017.820.014.770.010.760.026–Br(a)4
.270.034.660.023.020.03(–0.47)I?ei?oea. O aeoaeeao i?ecaaaeai? ioe?ii/i?
cia/aiiy, ia/eneai? ia i?aenoaa? aca?iii? ei?aeyoe?? i?ae pK2 oa pK1.

Ia i?aenoaa? aiae?co aaee/ei ?Ea (oaae. 2.) oa ci?i o niaeo?ao i?e
aa??thaaii? ?I iiaea aooe cai?iiiiiaaia caaaeueia noaia i?ioie?oe/ieo
??aiiaaa oa ?aaeoe?? a?ae?ie?co aeine?aeaeoaaieo niieoe.

Noaia 1

Cia/aiiy ?Ea, ui oa?aeoa?ecothoue eeneioi?noue a?ae?ieneiio?aeieo
?i?iieoia?eio oa eoia?eio (Oaae. 3) aeicaieythoue c?iaeoe aeniiaie, ui
a?ae?ieneeueiee i?ioii o eoia?eiao ? a?eueo ?ooeeaei, ai?ae o
a?aeiia?aeieo ?i?iieoia?eiao (D?Ea ~ 0.6). Oea iia’ycaii c aeae?eueea
a?eueo aenieith aeaeo?iiiaeoeaioi?iith caeaoi?noth ea?aii?eueii? a?oie o
ii??aiyii? c ?i?iia?oiith. Cia/ii iaioa ia eeneioi?noue a?ae?ienea?oie
ye o ?i?iieoia?eiao, oae ? o eoia?eiao aieeaa? ci?ia ai?aeii? a?oie ia
iaio aeoeaioi?iee aaicei?aeacieueiee o?aaiaio (D?Ea ~ 0.25). Oea
iiaea aooe iaoiiaeaii ye iai oith ??cieoeath a aeoeaioi?i?e caeaoiino?
oeeo a?oi, oae ? iaioith i?iaiaeei?noth aeaeo?iiiiai aieeao cai?niee?a
ii eaioethao aoii?a N3 — N7, o ii??aiyii? c eaioethaii aoii?a N2 — N7.

Oaaeeoey 3

Cia/aiiy a?ae’?iieo eiaa?eoi?a eiinoaio eeneioii? aeenioe?aoe?? (?Ea)
7-a?ae?ienecai?uaieo ?i?iieoia?ei?a (IVa, Va), eoia?ei?a (VIa, VIIa) oa
nieae 2-ai?ii-1-aaicii??ee?th VIII-XI.

Niieoea?EaNiieoea?EaIVa7.96 0.01VIII3.0 0.1Va8.18 0.01IX4.95
0.02VIa7.58 0.01X5.36 0.01VIIa7.25 0.01XI7.11 0.01Cia/aiiy pKa aeey
eao?iio 2-ai?ii-3-oe?aii-1-aaicii??ee?th VIII ? cia/ii ieae/eie o
ii??aiyii? ?c niieoeaie Ia oa IIa (Oaae 3.). Ia iaoo aeoieo, oea
iia’ycaii ?c a?eueoith aeaeo?iiiaeoeaioi?iith caeaoi?noth i?o?eeueii?
a?oie ii??aiyii c aaicei?aeacieueiith oa ai?aeiith a?oiaie, a oaeiae ? c
iaiiaeeea?noth ooai?aiiy aioo??oiueiiieaeoey?iiai aiaeiaaiai ca’yceo a
niieooe? VIII. Ni?anoaaeaiiy cia/aiue pKa nieae IX — XI c
iaiaoeeueiaaieie aiaeiaaie (Ia, IIa oa IIa) na?ae/eoue, ui iaoeethaaiiy
ai?iia?oie a nieyo 2-ai?ii-1-aaicii??ee?th ia i?ecaiaeeoue aei nooo?aeo
ci?i N-H eeneioiino? oeeo niieoe.

Aeey niieoe (Ia-a,a) — (IIIa-a,a) onoaiiaeaii aeia?o ei?aeyoe?th
cia/aiue lgKa c +-eiinoaioaie cai?niee?a R: (I: 0.99, r 0.973, II:
0.93, r 0.977, III: 0.51, r 0.991). Iaei??th c iniaeeainoae, ye?
oa?aeoa?ecothoue iaae?ei?noue oeeo ei?aeyoe?ei?o caeaaeiinoae, ? oe?ieee
ae?aiacii ci?i +-eiinoaio (+ 2.46). Niieoee c
2,3,4,6,7,8-aaenaa?ae?io?iie?ceiiaei cai?nieeii (ae) i?e ?ic?aooaaii?
ia?aiao??a oe??? ei?aeyoe?eii? caeaaeiino? ia a?aoiaoaaeinue, ine?eueee
a e?oa?aoo?? aei inoaiiueiai /ano aeai? uiaei +-eiinoaioe oeueiai
cai?nieea aoee a?aenooi?ie. ?acii c oeei, iayai?noue o?ueio iacaeaaeieo
e?i?eieo ei?aeyoe?e aeicaieeea iai ioe?ieoe aaee/eio + aeey
ij-eiiaeainiaaii? 2,3,4,6,7,8-aaenaa?ae?io?iie?ceiiai? a?oie (–2.9).

C o?aooaaiiyi aeaieo uiaei iaoai?cio oa eiinoaio i?ioie?oe/ieo ??aiiaaa,
iiaeia ioe?ieoe a?aeiinio no?ee?noue aei a?ae?ie?co eiaeii? ?c
i?ioie?oe/ieo oi?i, ye? ooai?ththoueny o ?ic/ei?. Aeine?aeaeaiiy
?aaeoe?? a?ae?ie?co a ?yaeo niieoe (IX) — (XI) iieaco?, ui, a
caeaaeiinoe a?ae cai?nieea a iieiaeaii? 3, aieea iaoeethaaiiy ai?iia?oie
ia no?ee?noue eao?iio 2-ai?ii-1-aaicii??ee?th ? ??ciei. Aeey ia?e niieoe
c ai?aeiei cai?nieeii (Ia oa IX) eiinoaioa a?ae?ie?co aiane?aeie
iaoeethaaiiy cieaeaia i?eaeecii ia ii?yaeie (2.16 10-4 oa 2.3 10-5),
oiae? ye aeey ia?e niieoe c aaicei?aeacieueiei cai?nieeii (IIa oa X) —
i?eaeecii a 5 ?ac?a (1.65 10-4 oa 3.47 10-5), a aeey a?aeiia?aeieo ?i
aeeeao?ii?a — a 16 ?ac?a (2.17 10-3 oa 1.35 10-4).

Ei?aeyoe?y cia/aiue lgkI oa lgkII (Noaia 1), yea anoaiiaeaia naia c
+-eiinoaioaie cai?niee?a o iieiaeaiiyo 6 oa 7 ( = – 1.1, r = 0.994, n =
6 ? = – 0.73, r = 0.994, n = 6 a?aeiia?aeii), a oaeiae aeecuee?
cia/aiiy -eiinoaio, ui oa?aeoa?ecothoue i?ioeane eeneioii-iniiaii?
??aiiaaae oa a?ae?ie?co nieae II, aeicaieythoue i?eionoeoe, ui o
noaae??, yea aecia/a? oaeaee?noue ?aaeoe?? a?ae?ie?co, aa?a o/anoue
eao?ii 2-ai?ii-1-aaicii??ee?th.

Ioaea, iiaeia c?iaeoe aeniiaie, ui noaae??th, yea aecia/a? oaeaee?noue
a?ae?ie?co, ? i?e?aeiaiiy iieaeoee aiaee aei aoiio ea?aiio a iieiaeaii?
2 eao?iio 2-ai?ii-1-aaicii??ee?th c ooai?aiiyi oao?aaae?e/iiai
?ioa?iaae?aoo (OE):

Noaia 2

Oaooiia??y iio?aeieo 7-a?ae?iene?i?iieoia?eio

I?e i?iaaaeaii? eeneioii-iniiaiiai oeo?oaaiiy 7-a?ae?ieneiio?aeieo nieae
aaicii??ee?th (Ia oa IIa) o aiaeii-nie?oiaiio ?ic/ei? aoei aeyaeaii, ui
niaeo?e iiaeeiaiiy iaeo?aeueieo oi?i nooo?ai a?ae??ciythoueny ye a?ae
niaeo??a a?aeiia?aeieo 7-a?ae?iene?i?iieoia?ei?a (IVa oa Va) a
aoeaoii?o?ee?, oae ? a?ae niaeo??a 7-iaoiene?i?iieoia?ei?a (IVa oa Va) o
aiaeii-nie?oiaiio ?ic/ei?.

?en. 2. Aeaeo?iii? niaeo?e iiaeeiaiiy i?ioie?oe/ieo oi?i niieoee (Va) o
ii??aiyii? ?c niaeo?ii niieoee (Va) a 50 ia.%-ii? aiaeii-aoaiieueii?
noi?o?. 1- oi?ia (Va), 2 — (IIa), 3 — ai?ii (V-a), 4 — noi?o oaooiia??a
(Va) oa (Vo), yea ooai?th?oueny i?e ?ic/eiaii? niieoee (Va), 5 — (Vo)
(niaeo? ?ic/eio niieoee (Va) o 5 ia.%-ii? aiaeii-aoaiieueii? noi?o?).

O ca’yceo c oei, ui o aiaeii-nie?oiaiio na?aaeiaeu? (50% ia.) noi?o
i?ioie?oe/ieo oi?i, ye? ooai?ththoueny, oeo?o?oueny ye ?aeeia /anoea,
oiaoi ni?aa?aeiioaiiy i?ae ieie ia caeaaeeoue a?ae ?I, iiaeia c?iaeoe
aeniiaie, ui oeae aoaeo i?e ci?i? eiioeaio?aoe?? aiaee a i?aai?/iiio
?ic/eiieeo iaoiiaeaii anoaiiaeaiiyi oaooiia?ii? ??aiiaaae i?ae oi?iaie
(Va) oa (Vo) (Noaia 3).

?en. 3. Aeaeo?iii? niaeo?e iiaeeiaiiy niieoee (Va) o
aiaeii-aoeaoii?o?eeueieo ?ic/eiao c ??ciei ai?noii aiaee, iieue/e : 1 —
0; 2 — 4.70; 3 — 10.87; 4 — 17.05; 5 — 23.22; 6 — 32.39; 7 — 41.55; 8 —
50.72. Aeiaaeeia iiaeeiath/iai oa?o 1 ni, ii/aoeiaa eiioeaio?aoe?y
1.5410-5 iieue/e.

Aoei oaeiae onoaiiaeaii, ui oaooiia? (Vo) ia ooai?th?oueny a aacaiaeieo
ai?ioiiieo ?ic/eiieeao (aoeaoii?o?ee, ae?ienai), a aacaiaeieo nie?oao
a?i aeyaey? naaa o?eueee o niaeo?ao ethi?ianoeaioe??, eiee ye o aiae?
??aiiaaaa i?aeoe/ii iiai?noth ci?uaia o a?e eiai ooai?aiiy. Oaeei /eiii,
iiaeia c?iaeoe aeniiaie, ui aeey 7-a?ae?iene?i?iieoia?ei?a (IVa) oa (Va)
a iaeano? 11>?I>2 ?aae?co?oueny ianooiia nenoaia ??aiiaaa:

Noaia 3

Oaooiia? Vo oa?aeoa?eco?oueny iayai?noth iaaaoeaii? nieueaaoio?ii??, ui
i?ecaiaeeoue aei «?icieaaiiy» ?ciaanoe/ii? oi/ee a ANI
aiaeii-aoeaoii?o?eeueieo ?ic/ei?a ci?iii-

ai neeaaeo niieoee Va (?en. 3.). Oea aeaco? ia ciaioaiiy aeeiieueiiai
iiiaioo oe??? niieoee i?e caoaeaeaii?, a oaeiae ia a?aeiinii aeniea
cia/aiiy aeeiieueiiai iiiaioo a iniiaiiio noai?. ?ic?aooiie aeaeo?iiii?
aoaeiae aeey iioei?ciaaii? aaiiao??? oaooiia??a Va oa Vo iaoiaeii AI1
iieacaa, ui ?o aeeiieuei? iiiaioe neeaaeathoue 3.4 D oa 6.1 D, a oaieioe
ooai?aiiy 55.3 eeae/iieue oa 63.5 eeae/iieue a?aeiia?aeii. Oaeei /eiii,
iaea?aeai? ?ic?aooieia? aeai? ocaiaeaeothoueny c aeniiaeii i?i aenieo
iiey?i?noue oaooiia?a o, a oaeiae aeacothoue ia cia/ii a?eueoo
no?ee?noue (I = 8.2 eeae/iieue) oi?ie Va o a?aenooiino? ?ic/eiieea.
Aeei?enoiaoth/e iaoiae aaeaioieo noai, iiaeia cia?aceoe no?oeoo?i?
oi?ioee niieoe IVo oa Vo o aeaeyae? noia?iiceoe?? aeaio a?ai?/ieo
?aciiainieo no?oeoo?:

Ia i?aenoaa? iaaaaeaieo aeua aeaieo, iiaeia c?iaeoe aeniiaie, ui aianie
oea?ooa??iiii? a?iiaoe/ii? no?oeoo?e ? i?aaaaeath/ei, oiio aeey
cia?aaeaiiy iieaeoe aenieiiiey?ieo oaooiia??a IVo oa Vo aeioe?eueiei ?
aeei?enoaiiy oea?ooa??iiii? no?oeoo?ii? oi?ioee.

Caeaaei?noue niaeo?aeueieo aeanoeainoae aeine?aeaeaieo niieoe a?ae
+-eiinoaio cai?niee?a o iieiaeaii? 7

I?e ni?anoaaeaii? aeaeo?iiieo niaeo??a iiaeeiaiiy aeine?aeaeoaaieo
niieoe aoei anoaiiaeaii, ui aeey oaeeueiaeo /enae iaeneioi?a
aeiaaioaeeueiaeo nioa iiaeeiaiiy a on?o na??yo niieoe niinoa??aa?oueny
e?i?eia ei?aeyoe?y c +-eiinoaioaie aeiii?ieo cai?niee?a a iieiaeaii? 7.
O?aoiaoth/e oa, ui aia?a?y aeaeo?iiiiai ia?aoiaeo, yeo ?enia?eiaioaeueii
ioe?iththoue ii iieiaeaiith iaeneioio aeiaaioaeeueiai? nioae iiaeeiaiiy,
??aia ci?i? a?eueii? aia?a?? iieaeoee i?e ia?aoiae? a caoaeaeaiee noai,
iiaeia aaanoe oiiaio eiinoaioo EANI, ui oa?aeoa?eco? i?ioean iiaeeiaiiy
na?oea. C aiae?co iaea?aeaieo caeaaeiinoae (oaae. 4) aeo?ea?, ui aeey
aeine?aeaeaieo niieoe aaee/eia ci?ie aia?a?? aeiaaioaeeueiaiai ia?aoiaeo
a ia?oee caoaeaeaiee O?aie-Eiiaeii?anueeee noai ? o 4-6 ?ac?a a?eueo
/ooeeaith aei aieeao cai?nieea, /ei aaee/eia ci?ie aia?a?? iieaeoee i?e
aeenioe?aoe?? eao?ii?a (I)-(III).

Ii??aiyiiy eiinoaio + o ??cieo na??yo iieaco?, ui ?c ca?eueoaiiyi
aeoeaioi?ieo aeanoeainoae aaicii??aiiaiai oeeeeo /ooeea?noue iieiaeaiiy
nioae iiaeeiaiiy aei aieeao cai?nieea c?inoa?.

Oaaeeoey 4

Ia?aiao?e ei?aeyoe?eieo caeaaeiinoae lgKANI = rs+

r,
I(a-ae)II(a-ae)III(a-ae)IV(a-ae)V(a-ae)VI(a-ae)VII(a-ae)r0.9770.9740.980
0.9750.9600.9740.9846.35.25.95.24.24.75.5I?e oeueiio, yeui ci?ia aia?a??
aeiaaioaeeueiaiai ia?aoiaeo iaoiiaeaia o?euee? ci?iith aianeo noaio c
IC, oi ia? niinoa??aaoeny e?i?eia ei?aeyoe?y aia?a?? aeaeo?iiiiai
ia?aoiaeo c aaee/eiith IC.

O yeino? iiaeaeueieo niieoe aeey aeine?aeaeaiiy ia?aiino ca?yaeo i?e
iioe/iiio caoaeaeaii? aoei ia?aii ?yae ,-iaiane/aieo eaoii?a — iio?aeieo
aeeaaicioeioaio, ea?aacieo oa N-iaoeeea?aacieo, ye? oaeiae i?noyoue
oai?ei?iiaiiiiaee o?aaiaio (A) ?c cai?nieeii a i-iieiaeaii?:

Caaaeyee i?eaeecii iaeiaeiai? aeiaaeei? -nenoai o?aaiaio?a A ? A,
niinoa??aa?oueny aca?iiae?y i?ae o?aaiaioaie, yea i?ecaiaeeoue aei
aeieeiaiiy o ANI ia?aoiae?a «caaaeueiiiieaeoey?iiai oeio». Iaeiae,
oaeiae aoei anoaiiaeaii, ui a ANI oeeo niieoe niinoa??aathoueny aeaa
oeie nioa, ui ii-??ciiio ?aaaothoue ye ia aaaaeaiiy a aaicaiiaa yae?i
o?aaiaioo A cai?niee?a ??cii? aeaeo?iiii? i?e?iaee (R), oae ? ia ci?io
aeaeo?iiiaeiii?ii? caeaoiino? aaoa?iaoiio O a?oai?eaiiaiai oeeeeo.
Aiae?c aeaieo eaaioiaio?i?/ieo ?ic?aooie?a, ui aoee i?iaaaeai? iaoiaeii
III EA ?c aeei?enoaiiyi /enae i?aeo?aaiaioiiai ia?aiino ca?yaeo oa /enae
eieae?caoe?? caoaeaeaiiy ia o?aaiaioao, iieacaa, ui ia?ao?ae, yeee
noi?iaiaeaeo?oueny ia?aiinii ca?yaeo ?c cai?nieea R ia ea?aii?eueio
a?oio, ? iaeiieiio?ao?aoe?eiei o?eueee i?e R = N(CH3)2. Oiio oi?iaeueii
o?eueee aeey niieoe c oeei cai?nieeii aeiaaioaeeueiaee aeaeo?iiiee
ia?ao?ae iiaeia aaaaeaoe eeane/iei ia?aoiaeii ?c AIC. Iacaaaeath/e ia
oea, aeey oaeeueiaeo /enae iaeneioi?a nioa, ui aoee aeae?eai? a?ao?/ii c
aenia?eiaioaeueieo niaeo??a, ye? caciathoue aeiaaioaeeueiaee cnoa i?e
ca?eueoaii? aeaeo?iiiaeiii?ii? caeaoiino? cai?nieea R, niinoa??aa?oueny
oi?ioa e?i?eia ei?aeyoe?y c +-eiinoaioaie cai?niee?a R: r = 0.996, =
8.29, n = 4 (X = S); r = 0.999, = 8.08, n = 4 (X = NH); r = 0.993, =
8.81, n = 4 (X = NCH3). Oaeei /eiii, aeey oa?aeoa?enoeee aieeao
cai?nieea ia ANI ia ? iaia’yceiaei aeei?enoaiiy nioae IC. E??i oiai,
nioaa iiaeeiaiiy, yea ? iaea?eueo /ooeeaith aei aieeao cai?nieea iiaea ?
ia aooe aeiaaioaeeueiaith. I?e oeueiio aeinoaoiuei aeei?enooaaoe
a?ao?/ia ?icae?eaiiy oa iaae?eio ?aeaioeo?eaoe?th i?e?iaee aeaiiai
aeaeo?iiiiai ia?aoiaeo c aeei?enoaiiyi eaaioiaio?i?/ieo ?ic?aooie?a.

Iacaaaeath/e ia a?aeiinii aenie? eiao?oe?aioe ei?aeyoe?? (oaae. 4),
cia/aiiy oaeeueiaeo /enae iaeneioi?a aeey niieoe ?c o?iie?ceiiaei
cai?nieeii aeey on?o na??e nenoaiaoe/ii a?aeoeeythoueny a?ae
ei?aeyoe?eii? i?yii?. Aaaaeath/e, ui oe? a?aeoeeaiiy iaoiiaeai?
aeanoeainoyie caoaeaeaiiai noaio, ia i?aenoaa? iaea?aeaieo aeaieo c
aeei?enoaiiyi oeeeeo Ouei?noa?o, iaie aoei ioe?iaii eiinoaioe
aeenioe?aoe?? eao?ii?a (I) — (III) o caoaeaeaiiio O?aie-Eiiaeii?anueeiio
noai? c iaoith aeine?aeaeaiiy caeaaeiino? cia/aiue eiaa?eoi?a oeeo
eiinoaio a?ae aeaeo?iiiiai aieeao cai?niee?a.

O caoaeaeaiiio noai? caeaaei?noue pKa* a?ae +-eiinoaio cai?niee?a oaeiae
iiaeia ai?ieneioaaoe i?yiith e?i??th: (I(a-ae): r = 0.959, = 1.8;
II(a-ae): r = 0.997, = 1.7; III(a-ae): r = 0.819, = 1.3), iaeiae,
iecueeee eiao?oe?aio ei?aeyoe?? aeey niieoe III(a-ae) aeaco?, ui oaea
iaaeeaeaiiy ? iacaaeia?eueiei. Acaaae?, oey caeaaei?noue ia?
e?eaie?i?eiee oa?aeoa? (?en. 4.).

Iaea?aeai? cia/aiiy na?ae/aoue, ui o caoaeaeaiiio noai? i?ioean
aeenioe?aoe?? eao?ii?a (I)-(III) ? i?eaeecii o 2 ?ace a?eueo /ooeeaei
aei aieeao cai?nieea o ii??aiyii? c aeenioe?aoee?th a iniiaiiio noai?.
Oeae oaeo a?aeaeca?eaeth? cia/ia ca?eueoaiiy iiey?eciaiino?
aeine?aeaeoaaieo niieoe i?e caoaeaeaii?. Caeaaeiino? pKa—+ oaeiae
iathoue aeae e?eaeo, nooi?iue e?eaecie yeeo c?inoa? i?e ca?eueoaii?
aeoeaioi?ieo aeanoeainoae cai?nieea o iieiaeaii? 3. Iaeiae, aeey niieoe
(IIa)-(IIae) c aaicei?aeacieueiei cai?nieeii, yeee ? neaaeei
aeoeaioi?ii, caeaaei?noue pKa—+ caaeia?eueii iieno?oueny i?yiith e?i??th
(r = 0.980, = 0.83).

Oaaeeoey 5

Ci?ia eeneioiino? eao?ii?a I-III i?e caoaeaeaii? (pKa), oa ?o
eeneioi?noue o caoaeaeaiiio O?aie-Eiiaeii?anueeiio noai? (pKa*).

IIIIIIRpKapKa*pKapKa*pKapKa*H(a)1.16.01.77.0–
0.23.0OCH3(a)3.08.32.78.51.75.3OH(a)2.48.02.78.81.65.3Et2N(a)3.810.6
3.610.82.87.1Quin(ae)3.711.34.212.02.16.9

Ine?eueee aeey niieoe c i?yiei iiey?iei ni?yaeaiiyi +-eiinoaioe
oa?aeoa?ecothoue ci?io aaee/eie -aeaeo?iiiiai ca?yaeo i?ae aieeaii
cai?nieea ye ia ?aaeoe?eiiio oeaio??, oae ? ia naiiio cai?nieeo, iaie
aoei i?iaaaeaii ?ic?aooiee -aeaeo?iiieo oa?aeoa?enoee a iniiaiiio oa
ia?oiio caoaeaeaiiio noaiao iaoiaeii Ia??a-Ia?eca?a-Iiiea. I?e oeeo
?ic?aooieao aoei aeei?enoaii ianooiiee ?yae cai?niee?a o iieiaeaii? 7:
H, OCH3, OH, H2N, Me2N, Et2N, 2,3,4,6,7,8-aaenaa?ae?io?iie?cei?e
(Quin.). Aiae?c aeaieo ?ic?aooie?a iieaco?, ui niinoa??aa?oueny oi?ioa
e?i?eia ei?aeyoe?y aaee/ei -ca?yae?a ia aoiiao cai?niee?a a iniiaiiio
noai? c +-eiinoaioaie. Aeei?enoiaoth/e oe? caeaaeiino?, ye? aoee
iaea?aeai? aeey cai?niee?a a-ae, iaoiaeii aeno?aiieyoe?? aoei ioe?iaii
+-eiinoaioo aeey 2,3,4,6,7,8-aaenaa?ae?io?iie?ceiiai? a?oie. I?ney
ona?aaeiaiiy ii naie na??yo aoei iaea?aeaii cia/aiiy + = –2.82, ui ?
aeecueeei aei + = –2.9, iaea?aeaiiio iaie ia i?aenoaa?
aenia?eiaioaeueieo aeaieo.

Aeine?aeaeaiiy aaia?aoe?eii? caeaoiino? neioaciaaieo ?a/iaei iieacaei,
ui niieoee IIa oa IIae aaia?othoue eaca?ia aei?ii?ithaaiiy i?e eaiiia?e
iaea/oe? (oaae. 6.). Oe? eaca?i? aa?aieee oa?aeoa?ecothoueny oaeiae
cia/ii a?eueo aenieith oioino?ee?noth, ii??aiyii c e?aueie eaca?ieie
aa?aieeaie oeueiai ae niaeo?aeueiiai ae?aiaciio — eoia?eiii 153 oa
?iaeai?iii AE.

Oaaeeoey 6

Aaia?aoe?ei? oa?aeoa?enoeee nieae 2-ai?ii-1-aaicii??ee?th IIa, IIae.

NiieoeaEiioeaio?aoe?y, iieue/eEEAe, %Niaeo?aeueiee ae?aiacii
aaia?aoe??*Oioino?ee?noue, N1/2IIa 1.610-40.65550 – 56010IIae
1.810-41.10568 – 5788Eoia?ei 1531.910-40.43545 – 5734?iaeai?i
AE1.010-41.00585 – 6003*I?ei?oea. N1/2 — /enei ?iioeuen?a, i?ney yeiai
aia?a?y aaia?aoe?? cieaeo?oueny oaea?/e.

I?e iaea/oe? aeneia?iei eaca?ii (OaCl*, iae.= 308 ii) niieoee IIa oa
IIae oaeiae aoaeoeaii aaia?othoue eaca?ia aei?ii?ithaaiiy (?en. 5.).

?en. 5. Niaeo?e aaia?aoe?? aoaiieueieo ?ic/ei?a niieoe IIa (1) oa IIae
(2) ii??aiyii c aoaeiiii — ?iaeai?iii AE (3), i?e iaea/oe? aeneia?iei
(XeCl*) eaca?ii.

AENIIAEE

1. I?iaaaeaii neioac a?aeiinii iaeiaea/aieo eean?a aaoa?ioeeee?/ieo
niieoe — ?i?iieoia?ei?a oa nieae 2-ai?ii-1-aaicii??ee?th. Anoaiiaeaii
ni?aa?aeiioaiiy, ye? e?euee?nii iienothoue aieea cai?niee?a ia
?aaeoe?eio caeaoi?noue oa niaeo?aeuei? aeanoeaino? ?i?iieoia?ei?a oa
nieae 2-ai?ii-1-aaicii??ee?th. Na?aae iaea?aeaieo nieae
2-ai?ii-1-aaicii??ee?th ciaeaeaii aoaeoeai? eaca?i? aa?aieee.

2. Cai?iiiiiaaii iaeiinoaae?eiee iaoiae neioaco nieae
2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th, yeee iniiaaii ia
aca?iiae?? iio?aeieo nae?oeeeiaiai aeueaeaa?aeo c nieyie
2-oe?aiiiaoeeaaicei?aeacie?th. Iaoiae ia iio?aao? aeei?enoaiiy
eaoae?caoi?o oa i?ecaiaeeoue aei aenieeo ( 70%) aeoiae?a oe?eueiaeo
niieoe.

3. Iaea?aeaii aoaeoeai? eaca?i? aa?aieee aeey eaiiiai? oa eaca?ii?
(XeCl*) iaea/ee, aia?a?y aaia?aoe?? oa oioino?ee?noue yeeo i?e eaiiia?e
iaea/oe? o 2.5 ?ace ia?aaeuo? aiaeia?/i? oa?aeoa?enoeee e?auiai c
eaca?ieo aa?aiee?a, aeei?enoo?ieo o aeai?e niaeo?aeuei?e iaeano? —
eoia?eio 153
(4-o?eooi?iaoeeeoia?eii-[6,7,8-ij]-2,3,4,6,7,8-aaenaa?ae?io?iie?ceio).

4. Ia i?aenoaa? anoaiiaeaieo e?i?eieo ei?aeyoe?e eiaa?eoi?a eiinoaio
??aiiaaa oa oaeaeeinoae a?ae?ie?co c +-eiinoaioaie cai?niee?a
cai?iiiiiaaii iaoai?cie i?ioie?oe/ieo aca?iiae?e a ?yaeo
3,7-aeecai?uaieo eoia?ei?a oa ?i?iieoia?ei?a, ye? i?noyoue aeae?eueea
?aaeoe?eieo oeaio??a, a oaeiae iaoai?ci a?ae?ie?co iio?aeieo
?i?iieoia?eio o aiaeii-nie?oiaeo na?aaeiaeuao.

5. Aeyaeaii oa e?euee?nii ioa?aeoa?eciaaii oaooiia??th
7-a?ae?iene?i?iieoia?ei?a o noi?oao aoaiie — aiaea oa aoeaoii?o?ee —
aiaea. Cai?iiiiiaaii aeei?enoiaoaaoe oe? niieoee aeey niaeo?aeueiiai
aecia/aiiy yeino? inooee i?aai?/ieo ?ic/eiiee?a oa nooiaiy
a?ae?aoiaaiinoe ee?oeiieo iaia?ai o iaaeeei-a?ieia?/ieo aeine?aeaeaiiyo.

6. Ia i?aenoaa? anoaiiaeaieo e?i?eieo ei?aeyoe?e eiaa?eoi?a eiinoaio
i?ioie?oe/ieo ??aiiaaa c +-eiinoaioaie cai?niee?a, ye?
aeei?enoiaothoueny o ??aiyii? Aaiiaoa, aecia/aii +-eiinoaioo aeey
ij-eiiaeainiaaiiai 2,3,4,6,7,8-aaenaa?ae?io?iie?cei?eo a iiieiaeaii? (–
2.9), ui aeicaiey? nooo?ai (ia 0.8 iae.) iioe?eoe ?nioth/o oeaeo +-
eiinoaio aeey iaca?yaeaeaieo cai?niee?a.

Iniiai? ?acoeueoaoe aeena?oaoe?? iioae?eiaaii:

1. Yeaeo?iiiua niaeo?u iiaeiuaiey iai?aaeaeueiuo eaoiiia, i?iecaiaeiuo
aeeaaicioeioaia e ea?aaciea / N.I. Eiaaeaiei, A.I. Ieeeo/aiei, A.A.
Ea?an?a, A.O. Eaa?ooei // Oe?aeineee oeie/aneee aeo?iae. — 1986. — O.
52. — ? 8. — C. 866-872.

2. Neioac, i?ioieeoe/aneea ?aaiiaaney e onoie/eainoue nieae
2-aieii-3-(2-aaiceieaeacieee)-1-aaiciie?eeey a aiaeii-nie?oiaie n?aaea /
A.A. Ea?an?a, E.E. Eoeaoeeay, I.E. ?oaoeia, A.E. AEeeie, N.I.
ss?iieaiei, I.A. Iiiiia??a // AEo?iae iauae oeiee. — 1995. — O. 65. —
Aei. 9. — C. 1547-1557.

3. Oaooiia?ey e niaeo?aeueii-ethieianoeaioiua naienoaa i?iecaiaeiuo
2-eieii-7-aeae?ieneeoia?eia / A.E. Aiae?aaaa, A.I.Aei?ioaiei, A.A.
Ea?an?a, A.E. Iiaeeia // Eioi?iaoeeiiiea oaoiieiaee: iaoea, oaoieea,
oaoiieiaey, ia?aciaaiea, caei?iauea: Na. iao/. o?. Oa?uee. Ain.
Iieeoaoi. Oiea. Aui. 6. — *. 3. — Oa?ueeia. — 1998. — N. 241-244.

4. Ea?an?a A.A. Eaaioiai-oeie/aneee ?an/?o yeaeo?iiiaeiii?iie
niiniaiinoe caianoeoaeae, iaoiaeyueony o i?yiii iiey?iii nii?yaeaiee n
?aaeoeeiiiui oeaio?ii. // Eioi?iaoeeiiiea oaoiieiaee: iaoea, oaoieea,
oaoiieiaey, ia?aciaaiea, caei?iauea: Na. iao/. o?. Oa?uee. Ain.
Iieeoaoi. Oiea. Aui. 6. — *. 3. — Oa?ueeia. — 1998. — N. 296-298.

5. A. n. NNN? ? 1533607, H 01 S 3/213, C09 B 57/00. Aeoeaiay n?aaea
aeey eaca?a e niinia aa iieo/aiey / N.A. Aaoeua, A.A. Ea?an?a, A.A.
Iinoiaieeia, A.I. Ieeeo/aiei, A.E. Iiaeeia, A.A. Oa?eianeee (NNN?). — ?
4342188/25; Cayaeaii

14.12.87; Iioae. 27.03.95, Athe ? 9. — 4 n.

6. Neioac, i?ioie?oe/ia aeenioe?aoe?y oa noaa?euei?noue 3,7-cai?uaieo
nieae 2-(R-ai?ii)-1-aaicii??ee?th / I.I. Ea?anueia, E.E. Eoeaoeueea,
I.E. ?oaoeia, N.I. ss?iieaiei, I.I. Iiiiia?ueia // Oac. aeii. XVII
Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??, i. Oa?e?a, eenoiiaae 1995.
*.1. N. 130.

7. Ea?anueia I.I., Eoeaoeueea E.E., ?oaoeia I.E.
Niaeo?aeueii-ethi?ianoeaioi? oa eeneioii-iniiai? aeanoeaino?
3-(2-aaicei?aeacie?e)eoia?ei?a. // Oac. aeii. Oe?a?inueei? eiioa?aioe??
«O?i?y acioai?nieo aaoa?ioeeee?a» i. Oa?e?a, 1-3 aeiaoiy 1997 ?. N. 96.

AIIOAOe?ss

Ea?anueia I.I. Neioac, ?aaeoe?eia caeaoi?noue oa niaeo?aeuei?
aeanoeaino? iio?aeieo ?i?iieoia?eio. — ?oeiien.

Aeena?oaoe?y ia caeiaoooy a/aiiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.03. — i?aai?/ia o?i?y. — Oa?e?anueeee aea?aeaaiee
oi?aa?neoao, Oa?e?a, 1999.

Neioaciaaii nenoaiaoe/i? ?yaee 3-ai?iiea?aii?e- oa
3-(2-aaicei?aeacie?e)?i?iieoia?ei?a oa -eoia?ei?a, a oaeiae ?o
ia?oei?ao?a. Cai?iiiiiaaii iaeiinoaae?eiee iaoiae neioaco nieae
2-ai?ii-3-(2-aaicei?aeacie?e)-1-aaicii??ee?th, yeee i?ecaiaeeoue aei
i?aeaeuaiiy aeoiae?a i?iaeoeo?a. Iaea?aeaii aoaeoeai? eaca?i? aa?aieee
aeey eaiiiai? oa eaca?ii? (XeCl*) iaea/ee. Aeyaeaii oa e?euee?nii
ioa?aeoa?eciaaii oaooiia??th 7-a?ae?iene?i?iieoia?ei?a. Aecia/aii
eiinoaioe eeneioii-iniiaieo ??aiiaaa o aiaeii-nie?oiaiio na?aaeiaeu? a
iniiaiiio oa o caoaeaeaiiio noai?. Ca aeiiiiiaith anoaiiaeaieo e?i?eieo
ei?aeyoe?e lgKa — +-eiinoaioe cai?niee?a aecia/aia +-eiinoaioa
ij-eiiaeainiaaiiai 2,3,4,6,7,8-aaenaa?ae?io?iie?cei?eo o ia?a-iieiaeaii?
(–2.9). Anoaiiaeaii, ui i?e a?aeiinii iaeeo aaee/eiao
aioo??oiueiiieaeoey?iiai ia?aiino ca?yaeo (AIC) o caoaeaeaiiio noai?
caeaaei?noue pKa a?ae +-eiinoaio aeia?a ai?ieneio?oueny i?yiith e?i?ath.
C? c?inoaiiyi aaee/eie AIC c?inoa? e?eaecia oe??? caeaaeiino?.

Eeth/ia? neiaa: ?i?iieoia?ei, nie? 2-ai?ii-1-aaicii??ee?th, eaca?iee
aa?aiee, oaooiia??y, +-eiinoaioa, aioo?ioiueiiieaeoey?iee ia?aiin
ca?yaeo.

ABSTRACT

Karasyov A.A. Synthesis, reactivity and spectral properties of
iminocoumarin derivatives. — Manuscript.

Thesis for a candidate of science in chemistry by speciality 02.00.03 –
organic chemistry. — Kharkiv State University, Kharkiv, 1999.

Systematic series of 3-carbamoyl-, 3-(2-benzimidazolyl)iminocoumarins,
-coumarins and 2-amino-1-benzopyrylium salts were synthesized. New
one-step high yield synthesis of
2-amino-3-(2-benzimidazolyl)-1-benzopyrylium salts with were proposed.
New effective laser dyes for flash-lamp and eximer (XeCl*) pumping were
found within synthesized compounds. Tautomerizm of
7-hydroxyiminocoumarins were found out and quantitatively
charachterized. Acid-base equilibrium constants were obtained for
studied compounds in water-alcohol medium for the ground and first
excited singlet states. Using linear correlations between lgKa and
+-constants of substituents, +-constant for ij-condenced
2,3,4,6,7,8-hexahydroquinolizine in para-position was obtained (2.9). It
has been noted that correlation of +-constants within lgKa values for
excited state is linear if the amount of charge transfer is small.

Key words: iminocoumarin, 2-amino-1-benzopyrylium salts, laser dye,
tautomerizm, +constant, intramolecular charge transfer.

AIIIOAOeEss

Ea?an?a A.A. Neioac, ?aaeoeeiiiay niiniaiinoue e niaeo?aeueiua naienoaa
i?iecaiaeiuo eieiieoia?eia. — ?oeiienue.

Aeenna?oaoeey ia nieneaiea o/?iie noaiaie eaiaeeaeaoa oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.03. — i?aaie/aneay oeiey. — Oa?ueeianeee
ainoaea?noaaiiee oieaa?neoao, Oa?ueeia, 1999.

?aaioa iinayuaia onoaiiaeaieth niioiioaiee, eiee/anoaaiii iienuaathueo
aeeyiea caianoeoaeae ia ?aaeoeeiiioth niiniaiinoue e niaeo?aeueiua
naienoaa eieiieoia?eiia, eoia?eiia e nieae 2-aieii-1-aaiciie?eeey.

A ea/anoaa iauaeoia enneaaeiaaiey auee neioace?iaaiu 3-ea?aaiiee- e
3-(2-aaiceieaeacieee)eieiieoia?eiu, a oaeaea i?iaeoeou eo
acaeiiaeaenoaey n eeneioaie e aiaeie (niee 2-aieii-1-aaiciie?eeey,
2-(3-eoia?eiee)aaiceieaeacieey e niioaaonoaothuea eoia?eiu n
caianoeoaeyie R = 6-Br, H, 7-OCH3, 7-OH, 7(C2H5)2N,
[6,7,8-ij]-2,3,4,6,7,8-aaenaaeae?ioeiieeceiee). Aeey neioaca nieae
2-aieii-3-(2-aaiceieaeacieee)-1-aaiciie?eeey i?aaeeiaeai iiaue
iaeiinoaaeeeiue iaoiae neioaca, iniiaaiue ia acaeiiaeaenoaee
i?iecaiaeiuo naeeoeeeiaiai aeueaeaaeaea n ia?oei?aoii
2-oeeaiiiaoeeaaiceieaeacieey aac i?eiaiaiey eaoaeecaoi?a e i?eaiaeyuee e
nouanoaaiiiio oaaee/aieth auoiaeia (a 3-4 ?aca) niaaeeiaiee n aeiii?iuie
caianoeoaeyie a iieiaeaiee 7. Noiia?iua auoiaeu niioaaonoaothueo
3-(2-aaiceieaeacieee)eieiieoia?eiia

e -eoia?eiia, iieo/aiiuo ec nieae 2-aieii-1-aaiciie?eeey, ieacuaathony
oaeaea auoa, /ai i?e eniieueciaaiee iauai?eiyoie iaoiaeeee neioaca ii
Ei?aaiaaaeth. N eniieueciaaieai EE-niaeo?ineiiee e ?aioaaiino?oeoo?iiai
aiaeeca iieacaii, /oi a enneaaeoaiuo niaaeeiaieyo aaiceieaeacieueiue
o?aaiaio eaaeeo a ieineinoe aaiciie?aiiaiai oeeeea aneaaenaea
ia?aciaaiey aioo?eiieaeoey?iie aiaei?iiie nayce.

I?e yoii onoaiiaeaii, /oi iieaeoeu ia?oei?aoa
2-aieii-3-(2-aaiceieaeacieee)-1-aaiciie?aii-[6,7,8-ij]-2,3,4,6,7,8-aaena
aeae?ioeiieeceiey iiaoo nouanoaiaaoue a aeaea aeaoo e?enoaeee/aneeo
iiaeeoeeaoeee. A iaeiie ec ieo iieaeoea nouanoaoao a aeaea noia?iiceoeee
eaoeiia e iaeo?aeueiie oi?iu (eieiieoia?eia), a i?ioeaieiiii yaeyaony
aeae?iaeeia?oei?ao-eii H(ClO4)2–, nouanoaiaaiea eioi?iai a e?enoaeeao
iaia?oaeaii aia?aua.

Ia iniiaaiee aiaeeca ecia?aiiuo eiinoaio i?ioieeoe/aneeo ?aaiiaanee e
nei?inoae aeae?ieeca i?aaeeiaeaiu iaoaieciu aeae?ieeca eieiieoia?eiia a
eeneie e uaei/iie n?aaeao. Onoaiiaeaiu eeiaeiua ei??aeyoeee eiaa?eoiia
eiinoaio ?aaiiaanee e nei?inoae aeae?ieeca n +-eiinoaioaie caianoeoaeae.
N eniieueciaaieai onoaiiaeaiiuo ei??aeyoeee eiaa?eoiia eiinoaio
i?ioieeoe/aneeo ?aaiiaanee o?ao iacaaeneiuo ?aaeoeeiiiuo na?ee auea
ii?aaeaeaia +-eiinoaioa aeey ij-eiiaeaine?iaaiiiai
2,3,4,6,7,8-aaenaaeae?ioeiieeceieea a ia?a-iieiaeaiee. Iieo/aiiia
cia/aiea (–2.9) iicaieyao nouanoaaiii ?anoe?eoue oeaeo +-eiinoaio
iaca?yaeaiiuo caianoeoaeae aeey eniieueciaaiey a ei??aeyoeeiiiii
aiaeeca.

Iaia?oaeaia e eiee/anoaaiii ioa?aeoa?eciaaia oaooiia?ey
7-aeae?ieneeieiieoia?eiia, aicieeathuay i?e aeiaaaeaiee aiaeu a
i?aaie/aneee ?anoai?eoaeue (yoaiie, aoeaoiieo?ee) e iaaethaeaaiay ii
niaeo?ai iiaeiuaiey aneaaenoaea cia/eoaeueiiai ?acee/ey a iieiaeaiee
aeeeiiiaieiiauo iiein oaooiia?ia (~ 5000 ni–1) e ii oaaee/aieth
eaaioiaiai auoiaea ethieianoeaioeee (io 0.2 aei 0.8). Oeacaiiua
niaeo?aeueiua eciaiaiey iicaieytho ?aeiiaiaeiaaoue
7-aeae?ieneeieiieoia?eiu aeey ?ac?aaioee ia eo iniiaa oeoi?anoeaioiuo
naini?iuo nenoai ii?aaeaeaiey ea/anoaa inooee ?anoai?eoaeae e
eniieueciaaiey a iaaeeei-aeieiae/aneeo enneaaeiaaieyo a ea/anoaa
niaeo?aeueiuo ciiaeia, /oanoaeoaeueiuo e noaiaie aeae?aoe?iaaiiinoe
eeaoi/iuo iaia?ai. Ia iniiaaiee aeaiiuo eaaioiaioeie/aneeo ?an/?oia,
i?iaaaeaiiuo n eniieueciaaieai iieoyiie?e/aneiai iaoiaea AI1, naeaeai
auaiae i oeaeooa?eiiiii yeaeo?iiiii no?iaiee aieaa iiey?iiai oaooiia?a.

Aeey naie ?aaeoeeiiiuo na?ee enneaaeoaiuo niaaeeiaiee onoaiiaeaiu
eeiaeiua ei??aeyoeee iaeneioiia aeeeiiiaieiiauo iiein iiaeiuaiey n
+-eiinoaioaie caianoeoaeae a iieiaeaiee 7. N eniieueciaaieai iaoiaea
aaeaioiuo noai e i?eaea/aieai iiaeaee aioo?eiieaeoey?iiai ia?aiina
ca?yaea aeaii iainiiaaiea ei??aeoiinoe eniieueciaaiey +-eiinoaio aeey
ei??aeyoeeiiiiai aiaeeca n oa?aeoa?enoeeaie yeaeo?iiiuo ia?aoiaeia. Ia
i?eia?a YNI iiaeaeueiuo niaaeeiaiee — i?iecaiaeiuo oaeeiia, iniiaiui
o?iiioi?ii eioi?uo, eae e a eoia?eiao yaeyaony caiau?iiue
oaieei?iiaiiiiaue o?aaiaio, iieacaii, /oi n i?eaea/aieai aeaiiuo
eaaioiaioeie/aneeo ?an/aoia iaoiaeii III aiciiaeii aeinoaoi/ii
iaae?aeiia a?aoe/aneia auaeaeaiea iaeaieaa /oanoaeoaeueiie e aeeyieth
caianoeoaey iieinu iiaeiuaiey a YNI, aeaaea anee iia e ia yaeyaony
aeeeiiiaieiiaie. Iieacaii, /oi aeey ?anniao?eaaaiuo niaaeeiaiee oaeaea
iaaethaeaaony eeiaeiay ei??aeyoeey +-eiinoaio caianoeoaeae n iaeneioiaie
iiein iiaeiuaiey, iaeaieaa /oanoaeoaeueiuo e aeeyieth caianoeoaey.
I?aaeeiaeaii ii?aaeaeaiea +-eiinoaiou caianoeoaey eae aaee/eiu,
oa?aeoa?ecothuae noaiaiue ia?aiina ca?yaea n caianoeoaey ia inoaeueioth
/anoue iieaeoeu i?e enneaaeoaiii i?ioeanna.

N eniieueciaaieai oeeeea O??noa?a ii?aaeaeaiu eiinoaiou eeneioiie
aeennioeeaoeee o??o na?ee enneaaeoaiuo eaoeiiia a aicaoaeae?iiii
ninoiyiee. Iieacaii, /oi caaeneiinoue lgKa a aicaoaeae?iiii ninoiyiee io
+-eiinoaio a iauai neo/aa eiaao e?eaieeiaeiue oa?aeoa?, iaeiaei, aeey
eaoeiiia 2-aieii-1-aaiciie?eeey n aaiceieaeacieueiui caianoeoaeai,
yaeythueiny neaaui yeaeo?iiiaeoeaioi?ii, aeaiiay caaeneiinoue oi?ioi
iienuaaaony i?yiie eeieae (r = 0.997, n = 6, = – 1.7).

Onoaiiaeaiu eeiaeiua ei??aeyoeee -yeaeo?iiiuo ca?yaeia ia aoiiao
caianoeoaeae n +-eiinoaioaie yoeo aea caianoeoaeae. N eniieueciaaieai
yoeo caaeneiinoae auea ioeaiaia «oai?aoe/aneay» +-eiinoaioa aeey
ij-eiiaeaine?iaaiiiai 2,3,4,6,7,8-aaenaaeae?ioeiieeceieea. Iieo/aiiia
cia/aiea (– 2.82) ieacaeinue aeeceei e – 2.9, iieo/aiiiio iaie ia iniiaa
yenia?eiaioaeueiuo aeaiiuo.

Eeth/aaua neiaa: eieiieoia?ei, niee 2-aieii-1-aaiciie?eeey, eaca?iue
e?aneoaeue, oaooiia?ey, +-eiinoaioa, aioo?eiieaeoey?iue ia?aiin ca?yaea.

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