FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2079238029> ?p ?o ?g. }

• W2079238029 endingPage "3921" @default.
• W2079238029 startingPage "3914" @default.
• W2079238029 abstract "The long-lived radical cation of 2-methoxyethanol, CH3OCH2CH2OH•+, is stable toward isomerization in the gas phase. This radical cation reacts with neutral reagents via three main channels in a Fourier-transform ion cyclotron resonance mass spectrometer. CH3OCH2CH2OH•+ abstracts an electron from reagents with ionization energies less than that of CH3OCH2CH2OH. Neutral reagents with higher ionization energies replace CH3OCH2• or CH2O in the ion. Both replacement reactions are probably driven by the formation of a hydrogen bond between the entering nucleophile and the hydroxyl group in CH3OCH2CH2OH•+, which breaks the C−C bond in CH3OCH2CH2OH•+. For strong nucleophiles, this process is so exothermic that the resulting ion/molecule complex dissociates by loss of CH3OCH2•. However, weak nucleophiles yield a longer-lived ion−molecule complex. Within this complex, CH3OCH2• can react with the initially produced ion by replacement of CH2O (a weaker nucleophile) to yield the hydrogen-bridged complex of CH3OCH2• and the nucleophile. This reaction provides a general approach for the gas-phase synthesis of different hydrogen-bridged radical cations. Ab initio molecular orbital calculations suggest that the most stable geometry of CH3OCH2CH2OH•+ is characterized by an unusually long C−C bond (1.775 Å at the UMP2/6-31G** level of theory). This finding is in agreement with the observed facile cleavage of the C−C bond in CH3OCH2CH2OH•+. The isomeric ions •CH2O+(CH3)CH2OH, (CH3)2O+CH2O•, •CH2OCH2CH2OH2+, •CH2O(CH3)−H+···OCH2, and CH3OC(H)H···O(H)CH2•+ were calculated to be less stable than CH3OCH2CH2OH•+ (at the UMP2/6-31G**//UHF/6-31G**+ZPE level of theory). Only the ion (CH3)2O-H···OCH•+ was found to lie lower in energy than CH3OCH2CH2OH•+ (by 7.2 kcal/mol at the UMP2/6-31G**+ZPVE level of theory). However, experimental evidence does not support the formation of this hydrogen-bridged ion upon ionization of 2-methoxyethanol." @default.
• W2079238029 created "2016-06-24" @default.
• W2079238029 creator A5014811894 @default.
• W2079238029 creator A5032241820 @default.
• W2079238029 creator A5055155926 @default.
• W2079238029 creator A5056660920 @default.
• W2079238029 creator A5087057861 @default.
• W2079238029 date "1996-01-01" @default.
• W2079238029 modified "2023-09-27" @default.
• W2079238029 title "An Experimental and Theoretical Study of the Long-Lived Radical Cation of CH3OCH2CH2OH" @default.
• W2079238029 cites W1541393941 @default.
• W2079238029 cites W1964353419 @default.
• W2079238029 cites W1969691867 @default.
• W2079238029 cites W1973739954 @default.
• W2079238029 cites W1980161843 @default.
• W2079238029 cites W1980592603 @default.
• W2079238029 cites W1981012928 @default.
• W2079238029 cites W1981922370 @default.
• W2079238029 cites W1984970533 @default.
• W2079238029 cites W1988326242 @default.
• W2079238029 cites W1988411738 @default.
• W2079238029 cites W1998246830 @default.
• W2079238029 cites W2002092588 @default.
• W2079238029 cites W2015838306 @default.
• W2079238029 cites W2016279190 @default.
• W2079238029 cites W2017041290 @default.
• W2079238029 cites W2019555199 @default.
• W2079238029 cites W2022464228 @default.
• W2079238029 cites W2024070595 @default.
• W2079238029 cites W2030230761 @default.
• W2079238029 cites W2030685925 @default.
• W2079238029 cites W2036303221 @default.
• W2079238029 cites W2040030877 @default.
• W2079238029 cites W2042441476 @default.
• W2079238029 cites W2045942607 @default.
• W2079238029 cites W2054768776 @default.
• W2079238029 cites W2054812842 @default.
• W2079238029 cites W2061432822 @default.
• W2079238029 cites W2063222789 @default.
• W2079238029 cites W2068705550 @default.
• W2079238029 cites W2068825507 @default.
• W2079238029 cites W2088408771 @default.
• W2079238029 cites W2089011315 @default.
• W2079238029 cites W2089475916 @default.
• W2079238029 cites W2093062958 @default.
• W2079238029 cites W2094895295 @default.
• W2079238029 cites W2148941593 @default.
• W2079238029 cites W2170602429 @default.
• W2079238029 cites W2949147383 @default.
• W2079238029 cites W2949404676 @default.
• W2079238029 cites W2949939315 @default.
• W2079238029 doi "https://doi.org/10.1021/ja952145p" @default.
• W2079238029 hasPublicationYear "1996" @default.
• W2079238029 type Work @default.
• W2079238029 sameAs 2079238029 @default.
• W2079238029 citedByCount "2" @default.
• W2079238029 crossrefType "journal-article" @default.
• W2079238029 hasAuthorship W2079238029A5014811894 @default.
• W2079238029 hasAuthorship W2079238029A5032241820 @default.
• W2079238029 hasAuthorship W2079238029A5055155926 @default.
• W2079238029 hasAuthorship W2079238029A5056660920 @default.
• W2079238029 hasAuthorship W2079238029A5087057861 @default.
• W2079238029 hasConcept C112887158 @default.
• W2079238029 hasConcept C126661725 @default.
• W2079238029 hasConcept C134121241 @default.
• W2079238029 hasConcept C145148216 @default.
• W2079238029 hasConcept C147597530 @default.
• W2079238029 hasConcept C147789679 @default.
• W2079238029 hasConcept C161790260 @default.
• W2079238029 hasConcept C170552419 @default.
• W2079238029 hasConcept C178790620 @default.
• W2079238029 hasConcept C178907741 @default.
• W2079238029 hasConcept C185592680 @default.
• W2079238029 hasConcept C191897082 @default.
• W2079238029 hasConcept C192562407 @default.
• W2079238029 hasConcept C193055867 @default.
• W2079238029 hasConcept C32909587 @default.
• W2079238029 hasConcept C39527238 @default.
• W2079238029 hasConcept C40875361 @default.
• W2079238029 hasConcept C75473681 @default.
• W2079238029 hasConcept C96444392 @default.
• W2079238029 hasConceptScore W2079238029C112887158 @default.
• W2079238029 hasConceptScore W2079238029C126661725 @default.
• W2079238029 hasConceptScore W2079238029C134121241 @default.
• W2079238029 hasConceptScore W2079238029C145148216 @default.
• W2079238029 hasConceptScore W2079238029C147597530 @default.
• W2079238029 hasConceptScore W2079238029C147789679 @default.
• W2079238029 hasConceptScore W2079238029C161790260 @default.
• W2079238029 hasConceptScore W2079238029C170552419 @default.
• W2079238029 hasConceptScore W2079238029C178790620 @default.
• W2079238029 hasConceptScore W2079238029C178907741 @default.
• W2079238029 hasConceptScore W2079238029C185592680 @default.
• W2079238029 hasConceptScore W2079238029C191897082 @default.
• W2079238029 hasConceptScore W2079238029C192562407 @default.
• W2079238029 hasConceptScore W2079238029C193055867 @default.
• W2079238029 hasConceptScore W2079238029C32909587 @default.
• W2079238029 hasConceptScore W2079238029C39527238 @default.
• W2079238029 hasConceptScore W2079238029C40875361 @default.

• next