메뉴 건너뛰기




Volumn 24, Issue 7, 2013, Pages 1097-1101

Kinetic and thermodynamic control of protonation in atmospheric pressure chemical ionization

Author keywords

Atmospheric pressure chemical ionization; Kinetic control; Mass spectrometry; p (Dimethylamino)chalcone; Protonation; Thermodynamic control

Indexed keywords

ATMOSPHERIC PRESSURE CHEMICAL IONIZATION; BULKY SOLVENTS; CHALCONES; KINETIC CONTROL; KINETICALLY CONTROLLED; PROTON AFFINITY; PROTONATION SITE; THERMODYNAMIC CONTROL;

EID: 84879091959     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-013-0626-9     Document Type: Article
Times cited : (32)

References (32)
  • 1
    • 60149103143 scopus 로고    scopus 로고
    • Gas-phase versus liquid-phase structures by electrospray ionization mass spectrometry
    • 10.1002/anie.200805392 1:CAS:528:DC%2BD1MXit1Smt7c%3D
    • Tian, Z.; Kass, S.R.: Gas-phase versus liquid-phase structures by electrospray ionization mass spectrometry. Angew. Chem. Int. Ed. 48, 1321-1323 (2009)
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1321-1323
    • Tian, Z.1    Kass, S.R.2
  • 2
    • 79959774634 scopus 로고    scopus 로고
    • Infrared multiphoton dissociation spectroscopy study of protonated p-aminobenzoic acid: Does electrospray ionization afford the amino- or carboxy-protonated ion?
    • 10.1021/jp203829z 1:CAS:528:DC%2BC3MXntlCrtb8%3D
    • Schmidt, J.; Meyer, M.M.; Spector, I.; Kass, S.R.: Infrared multiphoton dissociation spectroscopy study of protonated p-aminobenzoic acid: does electrospray ionization afford the amino- or carboxy-protonated ion? J. Phys. Chem. A 115, 7625-7632 (2011)
    • (2011) J. Phys. Chem. A , vol.115 , pp. 7625-7632
    • Schmidt, J.1    Meyer, M.M.2    Spector, I.3    Kass, S.R.4
  • 3
    • 34247877609 scopus 로고    scopus 로고
    • Are carboxyl groups the most acidic sites in amino acids? Gas-phase acidity, H/D exchange experiments, and computations on cysteine and its conjugate base
    • 10.1021/ja0666194 1:CAS:528:DC%2BD2sXjvFKntbg%3D
    • Tian, Z.; Pawlow, A.; Poutsma, J.C.; Kass, S.R.: Are carboxyl groups the most acidic sites in amino acids? Gas-phase acidity, H/D exchange experiments, and computations on cysteine and its conjugate base. J. Am. Chem. Soc. 129, 5403-5407 (2007)
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 5403-5407
    • Tian, Z.1    Pawlow, A.2    Poutsma, J.C.3    Kass, S.R.4
  • 4
    • 50249116706 scopus 로고    scopus 로고
    • Does electrospray ionization produce gas-phase or liquid-phase structures?
    • 10.1021/ja802088u 1:CAS:528:DC%2BD1cXptVGjt74%3D
    • Tian, Z.; Kass, S.R.: Does electrospray ionization produce gas-phase or liquid-phase structures? J. Am. Chem. Soc. 130, 10842-10843 (2008)
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10842-10843
    • Tian, Z.1    Kass, S.R.2
  • 5
    • 61749094736 scopus 로고    scopus 로고
    • Are carboxyl groups the most acidic sites in amino acids? Gas-phase acidities, photoelectron spectra, and computations on tyrosine, p-hydroxybenzoic acid, and their conjugate bases
    • 10.1021/ja807982k 1:CAS:528:DC%2BD1MXnt1Gg
    • Tian, Z.; Wang, X.-B.; Wang, L.-S.; Kass, S.R.: Are carboxyl groups the most acidic sites in amino acids? Gas-phase acidities, photoelectron spectra, and computations on tyrosine, p-hydroxybenzoic acid, and their conjugate bases. J. Am. Chem. Soc. 131, 1174-1181 (2009)
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1174-1181
    • Tian, Z.1    Wang, X.-B.2    Wang, L.-S.3    Kass, S.R.4
  • 6
    • 70349734592 scopus 로고    scopus 로고
    • Gas-phase deprotonation of p-hydroxybenzoic acid investigated by IR spectroscopy: Solution-phase structure is retained upon ESI
    • 10.1021/ja903877v 1:CAS:528:DC%2BD1MXhtV2nsL7P
    • Steill, J.D.; Oomens, J.: Gas-phase deprotonation of p-hydroxybenzoic acid investigated by IR spectroscopy: solution-phase structure is retained upon ESI. J. Am. Chem. Soc. 131, 13570-13571 (2009)
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 13570-13571
    • Steill, J.D.1    Oomens, J.2
  • 7
    • 84866666933 scopus 로고    scopus 로고
    • Deprotonation of p-hydroxybenzoic acid: Does electrospray ionization sample solution or gas-phase structures?
    • 10.1021/ja3060589
    • Schröder, D.; Buděšínský, M.; Roithová, J.: Deprotonation of p-hydroxybenzoic acid: does electrospray ionization sample solution or gas-phase structures? J. Am. Chem. Soc. 134, 15897-15905 (2012)
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 15897-15905
    • Schröder, D.1    Buděšínský, M.2    Roithová, J.3
  • 8
    • 33845280094 scopus 로고
    • Factors determining relative sensitivity of analytes in positive mode atmospheric pressure ionization mass spectrometry
    • 10.1021/ac00164a012 1:CAS:528:DyaL1cXktFKgurk%3D
    • Sunner, J.; Nicol, G.; Kebarle, P.: Factors determining relative sensitivity of analytes in positive mode atmospheric pressure ionization mass spectrometry. Anal. Chem. 60, 1300-1307 (1988)
    • (1988) Anal. Chem. , vol.60 , pp. 1300-1307
    • Sunner, J.1    Nicol, G.2    Kebarle, P.3
  • 9
    • 42349090708 scopus 로고    scopus 로고
    • Atmospheric pressure chemical ionization source. 1. Ionization of compounds in the gas phase
    • 10.1021/ac800156y 1:CAS:528:DC%2BD1cXjsVWhsrc%3D
    • Andrade, F.J.; Shelley, J.T.; Wetzel, W.C.; Webb, M.R.; Gamez, G.; Ray, S.J.; Hieftje, G.M.: Atmospheric pressure chemical ionization source. 1. Ionization of compounds in the gas phase. Anal. Chem. 80, 2646-2653 (2008)
    • (2008) Anal. Chem. , vol.80 , pp. 2646-2653
    • Andrade, F.J.1    Shelley, J.T.2    Wetzel, W.C.3    Webb, M.R.4    Gamez, G.5    Ray, S.J.6    Hieftje, G.M.7
  • 11
    • 37249087212 scopus 로고    scopus 로고
    • A rationale for the linear correlation of aryl substituent effects in iron(0) tricarbonyl complexes containing α, β-unsaturated enone (chalcone) ligands
    • 10.1021/om7006425 1:CAS:528:DC%2BD2sXht1Cktb3I
    • Moulton, B.E.; Duhme-Klair, A.K.; Fairlamb, I.J.S.; Lynam, J.M.; Whitwood, A.C.: A rationale for the linear correlation of aryl substituent effects in iron(0) tricarbonyl complexes containing α, β-unsaturated enone (chalcone) ligands. Organometallics 26, 6354-6365 (2007)
    • (2007) Organometallics , vol.26 , pp. 6354-6365
    • Moulton, B.E.1    Duhme-Klair, A.K.2    Fairlamb, I.J.S.3    Lynam, J.M.4    Whitwood, A.C.5
  • 14
    • 33645222483 scopus 로고    scopus 로고
    • Fragmentation study of protonated chalcones by atmospheric pressure chemical ionization and tandem mass spectrometry
    • 10.1002/rcm.2404 1:CAS:528:DC%2BD28XjtFCgsLw%3D
    • Tai, Y.; Pei, S.; Wan, J.; Cao, X.; Pan, Y.: Fragmentation study of protonated chalcones by atmospheric pressure chemical ionization and tandem mass spectrometry. Rapid Commun. Mass Spectrom. 20, 994-1000 (2006)
    • (2006) Rapid Commun. Mass Spectrom. , vol.20 , pp. 994-1000
    • Tai, Y.1    Pei, S.2    Wan, J.3    Cao, X.4    Pan, Y.5
  • 15
    • 43449087648 scopus 로고    scopus 로고
    • Dissociative protonation and proton transfers: Fragmentation of α, β-unsaturated aromatic ketones in mass spectrometry
    • 10.1021/jo702464b 1:CAS:528:DC%2BD1cXjvFejur8%3D
    • Hu, N.; Tu, Y.-P.; Liu, Y.; Jiang, K.; Pan, Y.: Dissociative protonation and proton transfers: fragmentation of α, β-unsaturated aromatic ketones in mass spectrometry. J. Org. Chem. 73, 3369-3376 (2008)
    • (2008) J. Org. Chem. , vol.73 , pp. 3369-3376
    • Hu, N.1    Tu, Y.-P.2    Liu, Y.3    Jiang, K.4    Pan, Y.5
  • 16
    • 0032366914 scopus 로고    scopus 로고
    • Evaluated gas phase basicities and proton affinities of molecules: An update
    • 10.1063/1.556018 1:CAS:528:DyaK1cXjvVKgtLs%3D
    • Hunter, E.P.L.; Lias, S.G.: Evaluated gas phase basicities and proton affinities of molecules: an update. J. Phys. Chem. Ref. Data 27, 413-656 (1998)
    • (1998) J. Phys. Chem. Ref. Data , vol.27 , pp. 413-656
    • Hunter, E.P.L.1    Lias, S.G.2
  • 17
    • 0034273032 scopus 로고    scopus 로고
    • Thermodynamics of macroscopic and microscopic proton ionization from protonated 4-aminobenzoic acid in aqueous solution from 298.15 to 393.15 K
    • 10.1021/jp994379r 1:CAS:528:DC%2BD3cXltlansrs%3D
    • Zhang, X.X.; Oscarson, J.L.; Izatt, R.M.; Schuck, P.C.; Li, D.: Thermodynamics of macroscopic and microscopic proton ionization from protonated 4-aminobenzoic acid in aqueous solution from 298.15 to 393.15 K. J. Phys. Chem. B 104, 8598-8605 (2000)
    • (2000) J. Phys. Chem. B , vol.104 , pp. 8598-8605
    • Zhang, X.X.1    Oscarson, J.L.2    Izatt, R.M.3    Schuck, P.C.4    Li, D.5
  • 18
    • 0039047680 scopus 로고
    • Stable carbonium ions. LVIII. Carbon-13 resonance investigation of protonated carboxylic acids (carboxonium ions) and oxocarbonium ions (acyl cations)
    • 10.1021/ja01002a040 1:CAS:528:DyaF1cXos1Klsg%3D%3D
    • Olah, G.A.; White, A.M.: Stable carbonium ions. LVIII. Carbon-13 resonance investigation of protonated carboxylic acids (carboxonium ions) and oxocarbonium ions (acyl cations). J. Am. Chem. Soc. 89, 7072-7075 (1967)
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 7072-7075
    • Olah, G.A.1    White, A.M.2
  • 19
    • 0005503195 scopus 로고
    • 13C NMR determination of acid-base tautomerization equilibria
    • 10.1021/jo00178a024 1:CAS:528:DyaL2cXosFWntQ%3D%3D
    • 13C NMR determination of acid-base tautomerization equilibria. J. Org. Chem. 49, 691-696 (1984)
    • (1984) J. Org. Chem. , vol.49 , pp. 691-696
    • Laufer, D.A.1    Gelb, R.I.2    Schwartz, L.M.3
  • 21
    • 34547888313 scopus 로고    scopus 로고
    • Even-electron ions: A systematic study of the neutral species lost in the dissociation of quasi-molecular ions
    • 10.1002/jms.1234 1:CAS:528:DC%2BD2sXpsVGmsbg%3D
    • Levsen, K.; Schiebel, H.-M.; Terlouw, J.K.; Jobst, K.J.; Elend, M.; Preiβ, A.; Thiele, H.; Ingendoh, A.: Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions. J. Mass Spectrom. 42, 1024-1044 (2007)
    • (2007) J. Mass Spectrom. , vol.42 , pp. 1024-1044
    • Levsen, K.1    Schiebel, H.-M.2    Terlouw, J.K.3    Jobst, K.J.4    Elend, M.5    Preiß, A.6    Thiele, H.7    Ingendoh, A.8
  • 22
    • 33847020855 scopus 로고    scopus 로고
    • Study of methylation of nitrogen-containing compounds in the gas phase
    • 10.1002/jms.1154 1:CAS:528:DC%2BD2sXitVOgu7s%3D
    • Zhang, X.; Wang, H.; Liao, Y.; Ji, H.; Guo, Y.: Study of methylation of nitrogen-containing compounds in the gas phase. J. Mass Spectrom. 42, 218-224 (2007)
    • (2007) J. Mass Spectrom. , vol.42 , pp. 218-224
    • Zhang, X.1    Wang, H.2    Liao, Y.3    Ji, H.4    Guo, Y.5
  • 23
    • 11944257456 scopus 로고
    • Mass spectrometry of alkylbenzenes and related compounds. Part II. Gas phase ion chemistry of protonated alkylbenzenes (alkylbenzenium ions)
    • 10.1002/mas.1280090602 1:CAS:528:DyaK3MXht1Squ7s%3D
    • Kuck, D.: Mass spectrometry of alkylbenzenes and related compounds. Part II. Gas phase ion chemistry of protonated alkylbenzenes (alkylbenzenium ions). Mass Spectrom. Rev. 9, 583-630 (1990)
    • (1990) Mass Spectrom. Rev. , vol.9 , pp. 583-630
    • Kuck, D.1
  • 24
    • 33748300820 scopus 로고    scopus 로고
    • Protonated aromatics and arenium ions
    • Nibbering, N.M.M. (ed.) Elsevier, Amsterdam
    • Kuck, D.: Protonated aromatics and arenium ions. In: Nibbering, N.M.M. (ed.) Encyclopedia of mass spectrometry, 4, pp. 229-242. Elsevier, Amsterdam (2005)
    • (2005) Encyclopedia of Mass Spectrometry , vol.4 , pp. 229-242
    • Kuck, D.1
  • 25
    • 0000726050 scopus 로고
    • Site of gas-phase cation attachment. Protonation, methylation, and ethylation of aniline, phenol, and thiophenol
    • 10.1021/jo00174a016 1:CAS:528:DyaL2cXlsVOr
    • Wood, K.V.; Burinsky, D.J.; Cameron, D.; Cooks, R.G.: Site of gas-phase cation attachment. Protonation, methylation, and ethylation of aniline, phenol, and thiophenol. J. Org. Chem. 48, 5236-5242 (1983)
    • (1983) J. Org. Chem. , vol.48 , pp. 5236-5242
    • Wood, K.V.1    Burinsky, D.J.2    Cameron, D.3    Cooks, R.G.4
  • 26
    • 84989064888 scopus 로고
    • Effect of method of ion preparation on low-energy collision-induced dissociation mass spectra
    • 10.1002/oms.1210210604 1:CAS:528:DyaL2sXjtlemug%3D%3D
    • Nacson, S.; Harrison, A.G.; Davidson, W.R.: Effect of method of ion preparation on low-energy collision-induced dissociation mass spectra. Org. Mass Spectrom. 21, 317-319 (1986)
    • (1986) Org. Mass Spectrom. , vol.21 , pp. 317-319
    • Nacson, S.1    Harrison, A.G.2    Davidson, W.R.3
  • 27
    • 37049088868 scopus 로고
    • Proton transfer to the fluorine atom in fluorobenzene: A dramatic temperature dependence in the gas phase
    • Mason, R.; Milton, D.; Harris, F.: Proton transfer to the fluorine atom in fluorobenzene: a dramatic temperature dependence in the gas phase. J. Chem. Soc. Chem. Commun. 1453-1455 (1987)
    • (1987) J. Chem. Soc. Chem. Commun. , pp. 1453-1455
    • Mason, R.1    Milton, D.2    Harris, F.3
  • 28
    • 37049066581 scopus 로고
    • Site specific gas-phase protonation of 2-t-butylmaleates and 2-t-butylsuccinates upon chemical ionization: Stereochemical effects and kinetic control
    • Weisz, A.; Cojocaru, M.; Mandelbaum, A.: Site specific gas-phase protonation of 2-t-butylmaleates and 2-t-butylsuccinates upon chemical ionization: stereochemical effects and kinetic control. J. Chem. Soc. Chem. Commun. 331-332 (1989)
    • (1989) J. Chem. Soc. Chem. Commun. , pp. 331-332
    • Weisz, A.1    Cojocaru, M.2    Mandelbaum, A.3
  • 29
    • 84989092774 scopus 로고
    • Chemical ionization mass spectrometry of bifunctional compounds. The behavior of bifunctional compounds on protonation
    • 10.1002/oms.1210251205 1:CAS:528:DyaK3MXhsVantbs%3D
    • Nakata, H.; Suzuki, Y.; Shibata, M.; Takahashi, K.; Konishi, H.; Takeda, N.; Tatematsu, A.: Chemical ionization mass spectrometry of bifunctional compounds. The behavior of bifunctional compounds on protonation. Org. Mass Spectrom. 25, 649-654 (1990)
    • (1990) Org. Mass Spectrom. , vol.25 , pp. 649-654
    • Nakata, H.1    Suzuki, Y.2    Shibata, M.3    Takahashi, K.4    Konishi, H.5    Takeda, N.6    Tatematsu, A.7
  • 30
    • 0032787240 scopus 로고    scopus 로고
    • Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization
    • 10.1002/(SICI)1096-9888(199907)34:7<755: AID-JMS831>3.0.CO;2-J 1:CAS:528:DyaK1MXkslGjtr8%3D
    • Vais, V.; Etinger, A.; Mandelbaum, A.: Intramolecular proton transfers in stereoisomeric gas-phase ions and the kinetic nature of the protonation process upon chemical ionization. J. Mass Spectrom. 34, 755-760 (1999)
    • (1999) J. Mass Spectrom. , vol.34 , pp. 755-760
    • Vais, V.1    Etinger, A.2    Mandelbaum, A.3
  • 31
    • 0035043113 scopus 로고    scopus 로고
    • + ions of stereoisomeric diethers and hydroxy esters upon chemical ionization and collision-induced dissociation
    • 10.1002/jms.148 1:CAS:528:DC%2BD3MXjs1Wluro%3D
    • + ions of stereoisomeric diethers and hydroxy esters upon chemical ionization and collision-induced dissociation. J. Mass Spectrom. 36, 422-429 (2001)
    • (2001) J. Mass Spectrom. , vol.36 , pp. 422-429
    • Denekamp, C.1    Mandelbaum, A.2
  • 32
    • 79952500896 scopus 로고    scopus 로고
    • Kinetic Control of protonation in electrospray ionization
    • 10.1007/s13361-010-0037-0 1:CAS:528:DC%2BC3MXnt1Oit7c%3D
    • Joyce, J.R.; Richards, D.S.: Kinetic Control of protonation in electrospray ionization. J. Am. Soc. Mass Spectrom. 22, 360-368 (2011)
    • (2011) J. Am. Soc. Mass Spectrom. , vol.22 , pp. 360-368
    • Joyce, J.R.1    Richards, D.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.