EI/MS/MS spectra of N-monosubstituted cyanoacetamides
EI/MS/MS spektri N-monosupstituisanih cijanoacetamida
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The electron-ionization induced mass spectra of twenty six N-monosubstituted cyanoacetamides were recorded and their fragmentation patterns were studied. The effect of N-alkyl and N-aryl substituents to the fragmentation of the investigated compounds was discussed. Mechanistic generalization lead to a conclusion that fission of the carbon-carbon bonds next to carbonyl function or nitrogen were processes common for N-alkyl and N-(4-substituted phenyl) cyanoacetamides. In some amides, the elimination of the acyl group by a ketene fragment gave rise to the more stable ion. Cycloalkyl amides could not fragment by single carbon-carbon bond fission, but subsequent rearrangement resulted in formation of stable even electron ion. N-(4-substituted phenyl) cyanoacetamides were more stable showing also characteristic fragmentation depending on substituent present at phenyl ring.
U ovom radu su proučavani fragmentacioni putevi dvadeset šest N-monosupstituisanih cijanoacetamida dobijenih jonizacijom izazvanom bombardovanjem elektronima. Na osnovu definisanih fragmentacionih puteva diskutovan je uticaj prisutnih N-alkil i N-aril supstituenata. Sagledavanjem mehanizama fragmentacija ispitivanih N-monosupstituisanih cijanoacetamida uočava se da je cepanje veze ugljenik-ugljenik susedne karbonilnoj grupi ili azotu proces uočen i kod N-alkil i N-(4-supstituisanih fenil) cijanoacetamida. Kod nekih amida, eliminacija acil grupe u vidu fragmenta ketena dovodi do nastajanju stabilnijih jona. Cikloalkil amidi ne mogu da se fragmentišu samo cepanjem veze ugljenik-ugljenik, već u narednom koraku pregradnje daju stabilnije parne jone. N-(4-supstituisani fenil) cijanoacetamidi se stabilni u primenjenim jonizacionim uslovima i pokazuju karakteristične fragmentcije na koje utiče prisutni supstituent na fenilnom jezgru.
Кључне речи:
N-monosubstituted cyanoacetamides / electron impact / rearrangement / fragmentation / N-monosupstituisani cijanoacetamidi / elektron impakt / pregradnja / fragmentacijeИзвор:
Chemical Industry & Chemical Engineering Quarterly, 2010, 16, 4, 387-397Издавач:
- Association of the Chemical Engineers of Serbia
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-MPN2006-2010-142063)
DOI: 10.2298/CICEQ100421042I
ISSN: 1451-9372
WoS: 000285947500011
Scopus: 2-s2.0-78649848100
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Ilić, Nataša AU - Marinković, Aleksandar AU - Mijin, Dušan AU - Nevešćanin, Marina AU - Petrović, Slobodan PY - 2010 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1662 AB - The electron-ionization induced mass spectra of twenty six N-monosubstituted cyanoacetamides were recorded and their fragmentation patterns were studied. The effect of N-alkyl and N-aryl substituents to the fragmentation of the investigated compounds was discussed. Mechanistic generalization lead to a conclusion that fission of the carbon-carbon bonds next to carbonyl function or nitrogen were processes common for N-alkyl and N-(4-substituted phenyl) cyanoacetamides. In some amides, the elimination of the acyl group by a ketene fragment gave rise to the more stable ion. Cycloalkyl amides could not fragment by single carbon-carbon bond fission, but subsequent rearrangement resulted in formation of stable even electron ion. N-(4-substituted phenyl) cyanoacetamides were more stable showing also characteristic fragmentation depending on substituent present at phenyl ring. AB - U ovom radu su proučavani fragmentacioni putevi dvadeset šest N-monosupstituisanih cijanoacetamida dobijenih jonizacijom izazvanom bombardovanjem elektronima. Na osnovu definisanih fragmentacionih puteva diskutovan je uticaj prisutnih N-alkil i N-aril supstituenata. Sagledavanjem mehanizama fragmentacija ispitivanih N-monosupstituisanih cijanoacetamida uočava se da je cepanje veze ugljenik-ugljenik susedne karbonilnoj grupi ili azotu proces uočen i kod N-alkil i N-(4-supstituisanih fenil) cijanoacetamida. Kod nekih amida, eliminacija acil grupe u vidu fragmenta ketena dovodi do nastajanju stabilnijih jona. Cikloalkil amidi ne mogu da se fragmentišu samo cepanjem veze ugljenik-ugljenik, već u narednom koraku pregradnje daju stabilnije parne jone. N-(4-supstituisani fenil) cijanoacetamidi se stabilni u primenjenim jonizacionim uslovima i pokazuju karakteristične fragmentcije na koje utiče prisutni supstituent na fenilnom jezgru. PB - Association of the Chemical Engineers of Serbia T2 - Chemical Industry & Chemical Engineering Quarterly T1 - EI/MS/MS spectra of N-monosubstituted cyanoacetamides T1 - EI/MS/MS spektri N-monosupstituisanih cijanoacetamida EP - 397 IS - 4 SP - 387 VL - 16 DO - 10.2298/CICEQ100421042I ER -
@article{ author = "Ilić, Nataša and Marinković, Aleksandar and Mijin, Dušan and Nevešćanin, Marina and Petrović, Slobodan", year = "2010", abstract = "The electron-ionization induced mass spectra of twenty six N-monosubstituted cyanoacetamides were recorded and their fragmentation patterns were studied. The effect of N-alkyl and N-aryl substituents to the fragmentation of the investigated compounds was discussed. Mechanistic generalization lead to a conclusion that fission of the carbon-carbon bonds next to carbonyl function or nitrogen were processes common for N-alkyl and N-(4-substituted phenyl) cyanoacetamides. In some amides, the elimination of the acyl group by a ketene fragment gave rise to the more stable ion. Cycloalkyl amides could not fragment by single carbon-carbon bond fission, but subsequent rearrangement resulted in formation of stable even electron ion. N-(4-substituted phenyl) cyanoacetamides were more stable showing also characteristic fragmentation depending on substituent present at phenyl ring., U ovom radu su proučavani fragmentacioni putevi dvadeset šest N-monosupstituisanih cijanoacetamida dobijenih jonizacijom izazvanom bombardovanjem elektronima. Na osnovu definisanih fragmentacionih puteva diskutovan je uticaj prisutnih N-alkil i N-aril supstituenata. Sagledavanjem mehanizama fragmentacija ispitivanih N-monosupstituisanih cijanoacetamida uočava se da je cepanje veze ugljenik-ugljenik susedne karbonilnoj grupi ili azotu proces uočen i kod N-alkil i N-(4-supstituisanih fenil) cijanoacetamida. Kod nekih amida, eliminacija acil grupe u vidu fragmenta ketena dovodi do nastajanju stabilnijih jona. Cikloalkil amidi ne mogu da se fragmentišu samo cepanjem veze ugljenik-ugljenik, već u narednom koraku pregradnje daju stabilnije parne jone. N-(4-supstituisani fenil) cijanoacetamidi se stabilni u primenjenim jonizacionim uslovima i pokazuju karakteristične fragmentcije na koje utiče prisutni supstituent na fenilnom jezgru.", publisher = "Association of the Chemical Engineers of Serbia", journal = "Chemical Industry & Chemical Engineering Quarterly", title = "EI/MS/MS spectra of N-monosubstituted cyanoacetamides, EI/MS/MS spektri N-monosupstituisanih cijanoacetamida", pages = "397-387", number = "4", volume = "16", doi = "10.2298/CICEQ100421042I" }
Ilić, N., Marinković, A., Mijin, D., Nevešćanin, M.,& Petrović, S.. (2010). EI/MS/MS spectra of N-monosubstituted cyanoacetamides. in Chemical Industry & Chemical Engineering Quarterly Association of the Chemical Engineers of Serbia., 16(4), 387-397. https://doi.org/10.2298/CICEQ100421042I
Ilić N, Marinković A, Mijin D, Nevešćanin M, Petrović S. EI/MS/MS spectra of N-monosubstituted cyanoacetamides. in Chemical Industry & Chemical Engineering Quarterly. 2010;16(4):387-397. doi:10.2298/CICEQ100421042I .
Ilić, Nataša, Marinković, Aleksandar, Mijin, Dušan, Nevešćanin, Marina, Petrović, Slobodan, "EI/MS/MS spectra of N-monosubstituted cyanoacetamides" in Chemical Industry & Chemical Engineering Quarterly, 16, no. 4 (2010):387-397, https://doi.org/10.2298/CICEQ100421042I . .