Ionic liquids on the basis of 2,3,4,6,7,8,9,10-octahydropyrimido-[1,2-a] azepine (1,8-diazabicyclo[5.4.0]undec-7-ene)

Article abstract of DOI:10.1134/S1070428006070256

New ionic liquids containing alkyl and polyfluoroalkyl substituents and various anions were synthesized from 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a] azepinium ion (1,8-diazabicyclo[5.4.0]undec-7-en-8-ium). Their NMR spectra and miscibility with water and organic solvents were studied. Pleiades Publishing, Inc., 2006.

Full text of DOI:10.1134/S1070428006070256

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ꢉꢌ+ꢆꢄꢂꢌ+ꢏꢆꢄꢈꢎꢂꢇꢄPꢄꢍꢇ+ꢆꢄꢇꢌ+ꢏꢎꢄ &ꢄ105ꢄVSHFWUXPꢄ
ꢍ&'&Oꢏꢆꢄ ꢆꢄSSPꢓꢄꢀꢈꢎꢉꢇꢄꢍ&+ꢏꢆꢄꢀꢋꢎꢃꢅꢄꢍ&ꢏꢆꢄꢇꢇꢎꢊꢅꢄꢍ&ꢏꢆꢄ
ꢇꢅꢎꢊꢃꢄꢍ&ꢏꢆꢄꢇꢊꢎꢋꢋꢄꢍ&ꢏꢆꢄꢇꢃꢎꢇꢀꢄꢍ& ꢏꢆꢄꢉꢂꢎꢇꢇꢄꢍ&ꢏꢆꢄꢉꢃꢎꢊꢋꢄ
ꢍ&ꢏꢆꢄꢉꢃꢎꢋꢂꢄꢍ&+&+ꢏꢆꢄꢅꢉꢎꢋꢋꢄꢍ&ꢏꢆꢄꢀꢇꢁꢎꢈꢇꢄTꢄꢍ&)ꢆꢄ- ꢄ ꢄ
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ꢍ& ꢏꢆꢄꢈꢁꢎꢁꢃꢄꢍ&+ &+ &+ ꢏꢆꢄꢉꢂꢎꢂꢈꢄꢍ& ꢏꢆꢄꢉꢃꢎꢂꢅꢄꢍ& ꢏꢆꢄ
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ꢇꢎꢋꢅꢄPꢄꢍꢇ+ꢆꢄꢀꢁꢌ+ꢏꢆꢄꢈꢎꢊꢀꢄWꢄꢍꢇ+ꢆꢄꢉꢌ+ꢄRUꢄꢂꢌ+ꢆꢄ-ꢄ ꢄꢄ
ꢅꢎꢂꢄ+]ꢏꢆꢄꢈꢎꢊꢊꢄWꢄꢍꢇ+ꢆꢄꢂꢌ+ꢄRUꢄꢉꢌ+ꢆꢄ-ꢄ ꢄꢅꢎꢂꢄ+]ꢏꢆꢄꢈꢎꢃꢇꢄEUꢎVꢄ
ꢍꢇ+ꢆꢄꢇꢌ+ꢏꢆꢄꢉꢎꢃꢋꢄVꢄꢍꢇ+ꢆꢄ3K&+ ꢏꢆꢄꢊꢎꢇꢀꢄGꢄꢍꢇ+ꢆꢄRꢌ+ꢏꢆꢄꢄ
ꢊꢎꢈꢂꢄPꢄꢍꢈ+ꢆꢄSꢌ+ꢆꢄPꢌ+ꢏꢎꢄ &ꢄ105ꢄVSHFWUXPꢄꢍ&'&Oꢏꢆꢄ
ꢆꢄSSPꢓꢄꢀꢋꢎꢋꢋꢄꢍ&ꢏꢆꢄꢇꢇꢎꢈꢉꢄꢍ&ꢏꢆꢄꢇꢅꢎꢊꢃꢄꢍ&ꢏꢆꢄꢇꢃꢎꢁꢈꢄꢍ&ꢏꢆꢄ
ꢇꢃꢎꢋꢊꢄꢍ& ꢏꢆꢄꢉꢊꢎꢂꢀꢄꢍ&ꢏꢆꢄꢉꢋꢎꢈꢁꢄꢍ&ꢏꢆꢄꢅꢅꢎꢉꢉꢄꢍ&ꢏꢆꢄꢅꢂꢎꢊꢈꢄ
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ꢇꢃꢎꢉꢁꢄꢍ& ꢏꢆꢄꢈꢁꢎꢂꢂꢄꢍ&+ &+ &+ ꢏꢆꢄꢉꢊꢎꢈꢀꢄꢍ& ꢏꢆꢄꢉꢋꢎꢈꢇꢄ
ꢍ& ꢏꢆꢄꢅꢈꢎꢋꢈꢄꢍ&+ &+ &+ &+ ꢏꢆꢄꢅꢅꢎꢈꢈꢄꢍ& ꢏꢆꢄꢀꢂꢂꢎꢈꢂꢄ
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Oꢄꢀꢉꢎꢉꢃꢐꢄ1ꢄꢀꢀꢎꢉꢉꢎꢀ
ꢀꢈꢈꢎꢋꢊꢄꢍ&ꢏꢆꢄꢀꢂꢊꢎꢀꢉꢄꢍ& 1ꢏꢎꢄꢀ
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SSPꢓꢄꢀꢎꢅꢈꢄVꢄꢍꢇ+ꢆꢄꢃꢌ+ꢏꢆꢄꢀꢎꢂꢃꢄVꢄꢍꢉ+ꢆꢄꢊꢌ+ꢆꢄꢋꢌ+ꢏꢆꢄꢇꢎꢁꢋꢄPꢄ
ꢎꢊꢉꢄWꢄꢍꢈ+ꢆꢄ&+ꢆꢄ-ꢄ ꢄꢊꢎꢈꢄ+]ꢏꢆꢄꢀꢎꢀꢈꢄPꢄꢍꢇ+ꢆꢄ&+ &+ꢏꢆꢄ
ꢎꢈꢂꢄPꢄꢍꢇ+ꢆꢄ&+ &+ &+ ꢏꢆꢄꢀꢎꢅꢇꢄPꢄꢍꢂ+ꢆꢄꢊꢌ+ꢆꢄꢃꢌ+ꢆꢄꢄ ꢍꢇ+ꢆꢄꢈꢌ+ꢏꢆꢄꢇꢎꢊꢊꢄPꢄꢍꢇ+ꢆꢄꢀꢁꢌ+ꢏꢆꢄꢈꢎꢅꢀꢄWꢄꢍꢇ+ꢆꢄꢉꢌ+ꢄRUꢄꢂꢌ+ꢆꢄ
ꢋꢌ+ꢏꢆꢄꢀꢎꢃꢃꢄTXLQWꢄꢍꢇ+ꢆꢄꢈꢌ+ꢆꢄ-ꢄ ꢄꢅꢎꢋꢄ+]ꢏꢆꢄꢇꢎꢀꢉꢄVꢄꢍꢈ+ꢆꢄ -ꢄ ꢄꢅꢎꢂꢄ+]ꢏꢆꢄꢈꢎꢅꢊꢄWꢄꢍꢇ+ꢆꢄꢂꢌ+ꢄRUꢄꢉꢌ+ꢆꢄ-ꢄ ꢄꢅꢎꢊꢄ+]ꢏꢆꢄꢄ
&
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&
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ꢊꢎꢋꢄ+]ꢏꢆꢄꢊꢎꢅꢊꢄGꢄꢍꢇ+ꢆꢄRꢌ+ꢆꢄ-ꢄ ꢄꢃꢎꢁꢄ+]ꢏꢎꢄ &ꢄ105ꢄVSHFꢌꢄ VSHFWUXPꢄꢍ&'&O ꢏꢆꢄ ꢆꢄSSPꢓꢄꢀꢋꢎꢊꢊꢄꢍ& ꢏꢆꢄꢇꢇꢎꢈꢋꢄꢍ& ꢏꢆꢄ
5
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ꢀꢁꢊꢈꢄ
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ꢀ
ꢈꢉꢎꢈꢉꢄꢍ& ꢏꢆꢄꢀꢂꢊꢎꢇꢇꢄꢍ& 1ꢏꢎꢄ )ꢄ105ꢄVSHFWUXPꢄ -ꢄ ꢄꢂꢎꢂꢄ+]ꢏꢆꢄꢃꢎꢉꢊꢄWꢄꢍꢀ+ꢆꢄꢉꢌ+ꢆꢄ-ꢄ ꢄꢊꢎꢊꢄ+]ꢏꢆꢄꢋꢎꢊꢇꢄGꢄꢍꢇ+ꢆꢄ
ꢍ&'&Oꢏꢓꢄ ꢄ±ꢊꢃꢎꢈꢈꢄSSPꢎꢄ
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SSPꢓꢄꢀꢈꢎꢉꢅꢄꢍ&+ꢏꢆꢄꢀꢋꢎꢇꢃꢄꢍ&+&+ꢏꢆꢄꢈꢈꢎꢃꢋꢄꢍ&+&+ꢌ
ꢉꢋꢌꢁꢂꢁꢂꢃꢂꢃꢋ7HWUDIOXRURSURS\Oꢏꢋꢁꢂꢃꢂꢄꢂꢅꢂꢆꢂꢇꢂꢈꢂꢉꢊꢋ
RFWDK\GURS\ULPLGR>ꢉꢂꢁꢋD@D]HSLQꢋꢉꢋLXPꢀ SꢋWROXHQHꢋ
VXOIRQDWHꢀꢌ;ꢏꢄZDVꢄV\QWKHVL]HGꢄDVꢄGHVFULEHGꢄDERYHꢄIRUꢄ
VDOWꢄ,,ꢄIURPꢄFRPSRXQGꢄ,DꢄDQGꢄꢇꢆꢇꢆꢈꢆꢈꢌWHWUDIOXRURSURS\Oꢄ
&
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ꢀꢉꢅꢎꢉꢃꢄꢍ&ꢆꢄ&ꢏꢎꢄ
ꢉꢋ%XW\OS\ULGLQLXPꢀEURPLGHꢀꢌ;,,,ꢏꢄZDVꢄV\QWKHꢌ
SꢌWROXHQHVXOIRQDWHꢐꢄWKHꢄUHDFWLRQꢄPL[WXUHꢄZDVꢄVWLUUHGꢄꢄ VL]HGꢄDVꢄGHVFULEHGꢄDERYHꢄIRUꢄVDOWꢄ,,,ꢄIURPꢄS\ULGLQHꢄꢄ
IRUꢄꢉꢅꢄPLQꢄDWꢄꢂꢁƒ&ꢎꢄQ ꢄ ꢄꢀꢎꢅꢁꢁꢋꢎꢄ +ꢄ105ꢄVSHFWUXPꢄ DQGꢄH[FHVVꢄꢀꢌERURPREXWDQHꢎꢄ<LHOGꢄꢋꢉꢒꢆꢄPSꢄꢋꢋƒ&ꢎꢄꢄ
ꢍ&'&Oꢏꢆꢄ ꢆꢄSSPꢓꢄꢀꢎꢉꢃꢄPꢄꢍꢇ+ꢆꢄꢃꢌ+ꢏꢆꢄꢀꢎꢅꢅꢄPꢄꢍꢉ+ꢆꢄꢊꢌ+ꢆꢄ +ꢄ105ꢄVSHFWUXPꢄꢍ&'&1ꢏꢆꢄ ꢆꢄSSPꢓꢄꢁꢎꢋꢈꢄWꢄꢍꢈ+ꢆꢄ&+ ꢆꢄ
ꢋꢌ+ꢏꢆꢄꢀꢎꢊꢀꢄTXLQWꢄꢍꢇ+ꢆꢄꢈꢌ+ꢏꢆꢄꢇꢎꢈꢂꢄVꢄꢍꢈ+ꢆꢄ&+ ꢏꢆꢄꢈꢎꢀꢅꢄPꢄ -ꢄ ꢄꢊꢎꢈꢄ+]ꢏꢆꢄꢀꢎꢈꢅꢄPꢄꢍꢇ+ꢆꢄ&+ &+ ꢏꢆꢄꢉꢎꢊꢇꢄPꢄꢍꢇ+ꢆꢄ
ꢍꢃ+ꢆꢄꢇꢌ+ꢆꢄꢉꢌ+ꢆꢄꢂꢌ+ꢆꢄꢀꢁꢌ+ꢏꢆꢄꢉꢎꢇꢈꢄWꢎWꢄꢍꢇ+ꢆꢄ&+&)ꢆꢄ-ꢄ ꢄ 1&+ ꢏꢆꢄꢃꢎꢁꢃꢄWꢄꢍꢇ+ꢆꢄꢈꢌ+ꢆꢄꢅꢌ+ꢆꢄ-ꢄ ꢄꢂꢎꢇꢄ+]ꢏꢆꢄꢃꢎꢅꢅꢄWꢄꢄ
ꢀ
ꢇꢎꢇꢆꢄꢀꢎꢀꢄ+]ꢏꢆꢄꢅꢎꢊꢊꢄWꢎWꢄꢍꢀ+ꢆꢄ&+)ꢆꢄ-ꢄ ꢄꢅꢇꢎꢋꢆꢄꢉꢎꢇꢄ+]ꢏꢆꢄ ꢍꢀ+ꢆꢄꢉꢌ+ꢆꢄ-ꢄ ꢄꢊꢎꢅꢄ+]ꢏꢆꢄꢋꢎꢀꢉꢄPꢄꢍꢇ+ꢆꢄꢇꢌ+ꢆꢄꢂꢌ+ꢏꢐꢄWKHꢄ
ꢊꢎꢇꢃꢄGꢄꢍꢇ+ꢆꢄPꢌ+ꢆꢄ-ꢄ ꢄꢃꢎꢈꢄ+]ꢏꢆꢄꢊꢎꢂꢋꢄGꢄꢍRꢌ+ꢆꢄ-ꢄ ꢄꢃꢎꢈꢄ+]ꢏꢎꢄ &+ &+ &+ ꢄVLJQDOꢄZDVꢄREVFXUHGꢄE\ꢄWKHꢄVLJQDOꢄIURPꢄ
WKHꢄUHVLGXDOꢄSURWRQVꢄLQꢄWKHꢄVROYHQWꢎꢄ &ꢄ105ꢄVSHFWUXPꢄ
&
ꢄ105ꢄVSHFWUXPꢄꢍ&'&O ꢏꢆꢄ ꢆꢄSSPꢓꢄꢇꢀꢎꢉꢇꢄꢍ& ꢏꢆꢄ
ꢇꢀꢎꢃꢊꢄꢍ&+ꢏꢆꢄꢇꢅꢎꢅꢇꢄꢍ&ꢏꢆꢄꢇꢃꢎꢁꢂꢄꢍ&ꢏꢆꢄꢇꢋꢎꢉꢁꢄꢍ&ꢏꢆꢄꢈꢂꢎꢈꢋꢄ ꢍ&' &1ꢏꢆꢄ ꢆꢄSSPꢓꢄꢀꢈꢎꢂꢁꢄꢍ&+ ꢏꢆꢄꢀꢋꢎꢊꢁꢄꢍ&+ &+ ꢏꢆꢄ
ꢍ& ꢏꢆꢄꢉꢈꢎꢀꢀꢄꢍ& ꢏꢆꢄꢉꢃꢎꢀꢂꢄꢍ& ꢏꢆꢄꢅꢇꢎꢃꢁꢄꢍ& ꢏꢆꢄꢂꢈꢎꢋꢈꢄWꢄ ꢈꢈꢎꢃꢂꢄꢍ&+&+&+ꢏꢆꢄꢂꢀꢎꢋꢇꢄꢍ1&+ꢏꢆꢄꢀꢇꢋꢎꢁꢂꢄꢍ&ꢆꢄ&ꢏꢆꢄ
ꢀ
ꢉꢅꢎꢂꢈꢄꢍ&ꢆꢄ&ꢏꢆꢄꢀꢉꢂꢎꢈꢋꢄꢍ&ꢏꢎꢄ
ꢍ&+&)ꢆꢄ-ꢄ ꢄꢈꢁꢎꢇꢄ+]ꢏꢆꢄꢀꢁꢃꢎꢅꢈꢄWꢎWꢄꢍ&+)ꢆꢄ-ꢄ ꢄꢇꢅꢁꢎꢁꢆꢄ
ꢈꢅꢎꢈꢄ+]ꢏꢆꢄꢀꢀꢈꢎꢁꢇꢄWꢎWꢄꢍ&+ &) ꢆꢄ-ꢄ ꢄꢇꢅꢀꢎꢅꢆꢄꢇꢃꢎꢀꢄ+]ꢏꢆꢄ
ꢉꢋ%XW\OS\ULGLQLXPꢀ WULIOXRURPHWKDQHVXOIRQDWHꢀ
ꢀꢇꢊꢎꢃꢀꢄꢍ& ꢏꢆꢄꢀꢇꢋꢎꢋꢂꢄꢍ& ꢏꢆꢄꢀꢈꢀꢎꢈꢋꢄꢍ& ꢏꢆꢄꢀꢉꢅꢎꢊꢃꢄꢍ&ꢏꢆꢄ
ꢀꢂꢀꢎꢋꢈꢄꢍ& 1ꢏꢎꢄ )ꢄ105ꢄVSHFWUXPꢄꢍ&'&Oꢏꢆꢄ ꢆꢄSSPꢓꢄꢄ
±ꢀꢇꢉꢎꢈꢊꢄVꢄꢍꢇ)ꢆꢄ&+&)ꢏꢆꢄ±ꢀꢈꢃꢎꢇꢋꢄGꢄꢍꢇ)ꢆꢄ&+)ꢆꢄ-ꢄ ꢄꢄ
ꢌ;,9ꢏꢄZDVꢄV\QWKHVL]HGꢄDVꢄGHVFULEHGꢄDERYHꢄIRUꢄVDOWꢄ,9ꢎꢄ
LJKWꢄEURZQꢄOLTXLGꢆꢄQ ꢄ ꢄꢀꢎꢉꢂꢁꢂꢎꢄ +ꢄ105ꢄVSHFWUXPꢄ
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ꢍꢇ+ꢆꢄ&+ &+ꢏꢆꢄꢀꢎꢋꢃꢄPꢄꢍꢇ+ꢆꢄ&+ &+&+ꢏꢆꢄꢉꢎꢂꢃꢄWꢄꢍꢇ+ꢆꢄ
1
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&
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&+ꢆꢄ-ꢄ ꢄꢊꢎꢅꢄ+]ꢏꢆꢄꢃꢎꢁꢅꢄWꢄꢍꢇ+ꢆꢄꢈꢌ+ꢆꢄꢅꢌ+ꢆꢄ-ꢄ ꢄꢅꢎꢂꢄ+]ꢏꢆꢄ
ꢃꢎꢉꢊꢄWꢄꢍꢀ+ꢆꢄꢉꢌ+ꢆꢄ-ꢄ ꢄꢊꢎꢊꢄ+]ꢏꢆꢄꢃꢎꢋꢃꢄGꢄꢍꢇ+ꢆꢄꢇꢌ+ꢆꢄꢂꢌ+ꢆꢄ-ꢄ ꢄ
ꢅꢎꢅꢄ+]ꢏꢎꢄ &ꢄ105ꢄVSHFWUXPꢄꢍ&'&Oꢏꢆꢄ ꢆꢄSSPꢓꢄꢀꢇꢎꢊꢉꢄ
ꢍ&+ ꢏꢆꢄꢀꢃꢎꢂꢇꢄꢍ&+ &+ ꢏꢆꢄꢈꢇꢎꢃꢉꢄꢍ&+ &+ &+ ꢏꢆꢄꢂꢀꢎꢉꢁꢄ
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ꢉꢋꢌꢁꢂꢁꢂꢃꢂꢃꢋ7HWUDIOXRURSURS\Oꢏꢋꢁꢂꢃꢂꢄꢂꢅꢂꢆꢂꢇꢂꢈꢂꢉꢊꢋ
RFWDK\GURS\ULPLGR>ꢉꢂꢁꢋD@D]HSLQꢋꢉꢋLXPꢀ WULIOXRURꢋ
PHWKDQHVXOIRQDWHꢀ ꢌ;,ꢏꢄZDVꢄV\QWKHVL]HGꢄDVꢄGHVFULEHGꢄ
DERYHꢄIRUꢄVDOWꢄ,,ꢄIURPꢄFRPSRXQGꢄ,DꢄDQGꢄꢇꢆꢇꢆꢈꢆꢈꢌWHWUDꢌ
IOXRURSURS\OꢄWULIOXRURPHWKDQHVXOIRQDWHꢎꢄ<LHOGꢄꢊꢅꢒꢆꢄ
PSꢄꢊꢋ±ꢃꢁƒ&ꢎꢄ +ꢄ105ꢄVSHFWUXPꢄꢍ&'&O ꢏꢆꢄ ꢆꢄSSPꢓꢄ
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ꢍꢇ+ꢆꢄꢀꢁꢌ+ꢏꢆꢄꢈꢎꢂꢈꢄWꢄꢍꢇ+ꢆꢄꢇꢌ+ꢏꢆꢄꢈꢎꢊꢁꢄPꢄꢍꢉ+ꢆꢄꢉꢌ+ꢆꢄꢂꢌ+ꢏꢆꢄ
ꢀ
ꢉꢉꢎꢀꢇꢄꢍ& ꢆꢄ& ꢏꢆꢄꢀꢉꢅꢎꢁꢃꢄꢍ& ꢏꢎꢄ )ꢄ105ꢄVSHFWUXPꢄ
ꢍ&'&Oꢏꢓꢄ ꢄ±ꢊꢋꢎꢀꢈꢄSSPꢎꢄ)RXQGꢆꢄꢒꢓꢄ&ꢄꢉꢇꢎꢇꢇꢐꢄ+ꢄꢉꢎꢋꢂꢐꢄꢄ
ꢄꢀꢋꢎꢉꢉꢐꢄ1ꢄꢉꢎꢋꢉꢐꢄ6ꢄꢀꢁꢎꢃꢁꢎꢄ& + )126ꢎꢄ&DOFXODWHGꢆꢄ
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