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ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones

ESI-MS spektri 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinona

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2009
0352-51390903223M.pdf (1.005Mb)
Authors
Marinković, Aleksandar
Vasiljević, Tatjana
Laušević, Mila
Jovanović, Bratislav Ž.
Article (Published version)
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Abstract
Twelve 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones were investigated by tandem mass spectrometry using positive as well as negative electrospray ionization. The influence of the electron affinity of the substituent and the steric effect on the fragmentation is discussed. Pyridinones with a substituent of low proton affinity show loss of water, HCN or benzene from the pyridinone ring in the first step of MS2 fragmentations. Oppositely, if a substituent with high proton affinity is present on the phenyl ring in the 4-position of pyridinone, the fragmentation paths are complex, depending mainly on the substituent proton acceptor ability. Elimination of neutral molecules CO, HCN, H2O, PhH (benzene) or Ph and CN radicals are fragmentation processes common for all compounds in the subsequent steps of the fragmentations.
3-Cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinoni su ispitivani tandem masenom spektrometrijom korišćenjem pozitivne i negativne elektrosprej jonizacije. Ispitivan je uticaj supstituenata i sternog efekta na fragmentacije. Piridinoni koji imaju supstituente malog afiniteta prema protonu pokazuju gubitak vode, HCN ili benzena iz piridinonskog prstena u prvom koraku MS2 fragmentacija. Suprotno, ako je supstituent sa visokim afinitetom prema protonu prisutan na fenilnom prstenu u 4-položaju piridinona, složeni fragmentacioni putevi uglavnom zavise od jačine te interakcije. Eliminacije neutralnih molekula CO, HCN, H2O, PhH (benzen) ili Ph i CN radikala su fragmentacioni procesi uobičajeni za sva ispitivana jedinjenja u narednim fragmentacionim stupnjevima.
Keywords:
electro spray ionization / substituted pyridinones / tandem mass spectrometry
Source:
Journal of the Serbian Chemical Society, 2009, 74, 3, 223-235
Publisher:
  • Serbian Chemical Society, Belgrade
Funding / projects:
  • Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)

ISSN: 0352-5139

WoS: 000264850000001

Scopus: 2-s2.0-68949125634
[ Google Scholar ]
1
1
Handle
https://hdl.handle.net/21.15107/rcub_technorep_1375
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1375
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Marinković, Aleksandar
AU  - Vasiljević, Tatjana
AU  - Laušević, Mila
AU  - Jovanović, Bratislav Ž.
PY  - 2009
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1375
AB  - Twelve 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones were investigated by tandem mass spectrometry using positive as well as negative electrospray ionization. The influence of the electron affinity of the substituent and the steric effect on the fragmentation is discussed. Pyridinones with a substituent of low proton affinity show loss of water, HCN or benzene from the pyridinone ring in the first step of MS2 fragmentations. Oppositely, if a substituent with high proton affinity is present on the phenyl ring in the 4-position of pyridinone, the fragmentation paths are complex, depending mainly on the substituent proton acceptor ability. Elimination of neutral molecules CO, HCN, H2O, PhH (benzene) or Ph and CN radicals are fragmentation processes common for all compounds in the subsequent steps of the fragmentations.
AB  - 3-Cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinoni su ispitivani tandem masenom spektrometrijom korišćenjem pozitivne i negativne elektrosprej jonizacije. Ispitivan je uticaj supstituenata i sternog efekta na fragmentacije. Piridinoni koji imaju supstituente malog afiniteta prema protonu pokazuju gubitak vode, HCN ili benzena iz piridinonskog prstena u prvom koraku MS2 fragmentacija. Suprotno, ako je supstituent sa visokim afinitetom prema protonu prisutan na fenilnom prstenu u 4-položaju piridinona, složeni fragmentacioni putevi uglavnom zavise od jačine te interakcije. Eliminacije neutralnih molekula CO, HCN, H2O, PhH (benzen) ili Ph i CN radikala su fragmentacioni procesi uobičajeni za sva ispitivana jedinjenja u narednim fragmentacionim stupnjevima.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones
T1  - ESI-MS spektri 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinona
EP  - 235
IS  - 3
SP  - 223
VL  - 74
UR  - https://hdl.handle.net/21.15107/rcub_technorep_1375
ER  - 
@article{
author = "Marinković, Aleksandar and Vasiljević, Tatjana and Laušević, Mila and Jovanović, Bratislav Ž.",
year = "2009",
abstract = "Twelve 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones were investigated by tandem mass spectrometry using positive as well as negative electrospray ionization. The influence of the electron affinity of the substituent and the steric effect on the fragmentation is discussed. Pyridinones with a substituent of low proton affinity show loss of water, HCN or benzene from the pyridinone ring in the first step of MS2 fragmentations. Oppositely, if a substituent with high proton affinity is present on the phenyl ring in the 4-position of pyridinone, the fragmentation paths are complex, depending mainly on the substituent proton acceptor ability. Elimination of neutral molecules CO, HCN, H2O, PhH (benzene) or Ph and CN radicals are fragmentation processes common for all compounds in the subsequent steps of the fragmentations., 3-Cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinoni su ispitivani tandem masenom spektrometrijom korišćenjem pozitivne i negativne elektrosprej jonizacije. Ispitivan je uticaj supstituenata i sternog efekta na fragmentacije. Piridinoni koji imaju supstituente malog afiniteta prema protonu pokazuju gubitak vode, HCN ili benzena iz piridinonskog prstena u prvom koraku MS2 fragmentacija. Suprotno, ako je supstituent sa visokim afinitetom prema protonu prisutan na fenilnom prstenu u 4-položaju piridinona, složeni fragmentacioni putevi uglavnom zavise od jačine te interakcije. Eliminacije neutralnih molekula CO, HCN, H2O, PhH (benzen) ili Ph i CN radikala su fragmentacioni procesi uobičajeni za sva ispitivana jedinjenja u narednim fragmentacionim stupnjevima.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones, ESI-MS spektri 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridinona",
pages = "235-223",
number = "3",
volume = "74",
url = "https://hdl.handle.net/21.15107/rcub_technorep_1375"
}
Marinković, A., Vasiljević, T., Laušević, M.,& Jovanović, B. Ž.. (2009). ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 74(3), 223-235.
https://hdl.handle.net/21.15107/rcub_technorep_1375
Marinković A, Vasiljević T, Laušević M, Jovanović BŽ. ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones. in Journal of the Serbian Chemical Society. 2009;74(3):223-235.
https://hdl.handle.net/21.15107/rcub_technorep_1375 .
Marinković, Aleksandar, Vasiljević, Tatjana, Laušević, Mila, Jovanović, Bratislav Ž., "ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones" in Journal of the Serbian Chemical Society, 74, no. 3 (2009):223-235,
https://hdl.handle.net/21.15107/rcub_technorep_1375 .

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