Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations

Mormann M, Bashir S, Derrick PJ, Kuck D (2000)
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY 11(6): 544-552.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ;
Abstract / Bemerkung
The thermochemical acid/base properties of the six dihydroxybenzoic acids (x,y-DHB) as prototypical matrices used in matrix-assisted laser desorption/ionization (MALDI) have been investigated. The ground-state gas-phase basicities (GB) of the six DHB isomers and the gas-phase acidities (Delta G(acid)) of the corresponding radical cations ([x,y-DHB](.+)) have been determined by Fourier-transform ion cyclotron resonance mass spectrometry employing the thermokinetic method. The gas-phase basicities vary from 814 kJ mol(-1) for the least basic isomer, 3,5-DHB, to 831 kJ mol(-1) for the most basic isomer, 2,4-DHB. The obtained gas-phase acidities of the corresponding radical cations vary from 815 kJ mol-l for the most acidic species, 3,4-DHB to 858 kJ mol(-1) for the least acidic one, 2,5-DHB. The results indicate that ground-state proton transfer from the matrix radical cations to the analyte may play a role in the ionization process of MALDI, whereas proton transfer from protonated matrix molecules can be excluded. (J Am Soc Mass Spectrom 2000, 11, 544-552) (C) 2000 American Society for Mass Spectrometry.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
Band
11
Zeitschriftennummer
6
Seite
544-552
ISSN
eISSN
PUB-ID

Zitieren

Mormann M, Bashir S, Derrick PJ, Kuck D. Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. 2000;11(6):544-552.
Mormann, M., Bashir, S., Derrick, P. J., & Kuck, D. (2000). Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 11(6), 544-552. doi:10.1016/S1044-0305(00)00112-4
Mormann, M., Bashir, S., Derrick, P. J., and Kuck, D. (2000). Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY 11, 544-552.
Mormann, M., et al., 2000. Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 11(6), p 544-552.
M. Mormann, et al., “Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations”, JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, vol. 11, 2000, pp. 544-552.
Mormann, M., Bashir, S., Derrick, P.J., Kuck, D.: Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. 11, 544-552 (2000).
Mormann, Michael, Bashir, Sajid, Derrick, Peter J., and Kuck, Dietmar. “Gas-phase basicities of the isomeric dihydroxybenzoic acids and gas-phase acidities of their radical cations”. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY 11.6 (2000): 544-552.

19 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Photochemical Reactions of Aminonaphthols Caused by Laser Desorption/Ionization.
Nagoshi K, Inatomi K, Osaka I, Takayama M., Mass Spectrom (Tokyo) 5(1), 2016
PMID: 27563510
Gas-phase basicities of polyfunctional molecules. Part 2: Saturated basic sites.
Bouchoux G, Salpin JY., Mass Spectrom Rev 31(3), 2012
PMID: 21773983
Advances in top-down proteomics for disease biomarker discovery.
Calligaris D, Villard C, Lafitte D., J Proteomics 74(7), 2011
PMID: 21477672
Electrospray tandem quadrupole fragmentation of quinolone drugs and related ions. On the reversibility of water loss from protonated molecules.
Neta P, Godugu B, Liang Y, Simón-Manso Y, Yang X, Stein SE., Rapid Commun Mass Spectrom 24(22), 2010
PMID: 20973001
Positive chemical ionization (PCI)-like behavior of estradiol in matrix-assisted laser desorption/ionization.
Wang P, Kremsky JN, Giese RW., Rapid Commun Mass Spectrom 23(17), 2009
PMID: 19653205
Investigating the quantitative nature of MALDI-TOF MS.
Szájli E, Fehér T, Medzihradszky KF., Mol Cell Proteomics 7(12), 2008
PMID: 18653768
Ion formation mechanisms in UV-MALDI.
Knochenmuss R., Analyst 131(9), 2006
PMID: 17047796
Gas-phase catalysis by atomic and cluster metal ions: the ultimate single-site catalysts.
Böhme DK, Schwarz H., Angew Chem Int Ed Engl 44(16), 2005
PMID: 15779095
The gas-phase basicity and proton affinity of 1,3,5-cycloheptatriene--energetics, structure and interconversion of dihydrotropylium ions.
Salpin JY, Mormann M, Tortajada J, Nguyen MT, Kuck D., Eur J Mass Spectrom (Chichester) 9(4), 2003
PMID: 12939488
The deprotonation of benzyl alcohol radical cations: a mechanistic dichotomy in the gas phase as in solution.
Baciocchi E, Bietti M, Chiavarino B, Crestoni ME, Fornarini S., Chemistry 8(2), 2002
PMID: 11843165
Proton affinity and heat of formation of vinyloxy [CH2CHO]· and Acetonyl [CH2COCH3]· radicals.
Bouchoux G, Chamot-Rooke J, Leblanc D, Mourgues P, Sablier M., Chemphyschem 2(4), 2001
PMID: 23696486
Protonation thermochemistry of ethyl halides.
Bouchoux G, Caunan F, Leblanc D, Nguyen MT, Salpin JY., Chemphyschem 2(10), 2001
PMID: 23686878
Secondary ion-molecule reactions in matrix-assisted laser desorption/ionization
Knochenmuss R, Stortelder A, Breuker K, Zenobi R., J Mass Spectrom 35(11), 2000
PMID: 11114080

68 References

Daten bereitgestellt von Europe PubMed Central.


Karas, Int. J. Mass Spectrom. Ion Processes 78(), 1987

Spengler, Rapid Commun. Mass Spectrom. 5(), 1991

Karas, Mass Spectrom. Rev. 10(), 1991

Stahl, Anal. Chem. 63(), 1991
Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation.
Beavis RC, Chait BT., Rapid Commun. Mass Spectrom. 3(12), 1989
PMID: 2520224

Egge, Pure Appl. Chem. 63(), 1991

Hillenkamp, 1990

Danis, Org. Mass Spectrom. 27(), 1992

Montaudo, Anal. Chem. 66(), 1994

Bahr, Anal. Chem. 64(), 1992
Matrix-assisted laser desorption ionization mass spectrometry with 2-(4-hydroxyphenylazo)benzoic acid matrix.
Juhasz P, Costello CE, Biemann K., J. Am. Soc. Mass Spectrom. 4(5), 1993
PMID: 24234937

Vertes, Anal. Chem. 65(), 1993

Johnson, Int. J. Mass Spectrom. Ion Processes 139(), 1994

Vertes, Rapid Commun. Mass Spectrom. 4(), 1990

Vertes, Chem. Phys. Lett. 171(), 1990

Johnson, Rapid Commun. Mass Spectrom. 5(), 1991

Sundquist, Anal. Chim. Acta 247(), 1991

Zenobi, Mass Spectrom. Rev. 17(), 1998

Liao, J. Mass Spectrom. 30(), 1995

Ehring, Org. Mass Spectrom. 26(), 1992

Land, J. Am. Soc. Mass Spectrom. 9(), 1998

Land, Eur. Mass Spectrom. 5(), 1999
Matrix-assisted laser desorption ionization of neutral clusters composed of matrix and analyte molecules.
Krutchinsky AN, Dolguine AI, Khodorkovski MA., Anal. Chem. 67(13), 1995
PMID: 8694245

Meffert, Eur. Mass Spectrom. 1(), 1995

Meffert, Ber. Bunsenges. Phys. Chem. 102(), 1998

Ireland, Adv. Phys. Org. Chem. 12(), 1976

Huang, Int. J. Mass Spectrom. Ion Processes 175(), 1998

Gimon-Kinsel, J. Am. Chem. Soc. 119(), 1997

Calba, Rapid Commun. Mass Spectrom. 12(), 1998
Effects of heavy-atom substituents on matrices used for matrix-assisted laser desorption-Ionization mass spectrometry.
Preston Schaffter LM, Kinsel GR, Russell DH., J. Am. Soc. Mass Spectrom. 5(9), 1994
PMID: 24222027

Gimon, Org. Mass Spectrom. 27(), 1992

Chiarelli, Anal. Chem. 65(), 1993

Bökelmann, Eur. Mass Spectrom. 1(), 1995

Karbach, Rapid Commun. Mass Spectrom. 12(), 1998

Knochenmuss, Rapid Commun. Mass Spectrom. 10(), 1996

Amerom, Int. J. Mass Spectrom. 182/183(), 1999

Jørgensen, Eur. Mass Spectrom. 4(), 1998

Burton, Rapid Commun. Mass Spectrom. 11(), 1997

Steenvoorden, Eur. Mass Spectrom. 3(), 1997

Breuker, Int. J. Mass Spectrom. 184(), 1999

Price, J. Thermochim. Acta 327(), 1999

Horneffer, Int. J. Mass Spectrom. 185/186/187(), 1999

Kofel, Int. J. Mass Spectrom. Ion Processes 65(), 1985

Caravatti, Org. Mass Spectrom. 26(), 1991

Thölmann, J. Am. Chem. Soc. 113(), 1991

Adams, J. Chem. Phys. 72(), 1980

Bartmess, Vacuum 33(), 1983

Bouchoux, Int. J. Mass Spectrom. Ion Processes 153(), 1996

Bouchoux, J. Phys. Chem. 100(), 1996

Bouchoux, J. Am. Chem. Soc. 118(), 1996

Bouchoux, Rapid Commun. Mass Spectrom. 13(), 1999

Witt, Int. J. Mass Spectrom. Ion Processes 164(), 1997

Decker, Int. J. Mass Spectrom. 185/186/187(), 1999

Cooks, J. Mass Spectrom. 34(), 1999

Su, J. Chem. Phys. 76(), 1982

AUTHOR UNKNOWN, 0

Hunter, J. Phys. Chem. Ref. Data 27(), 1998

Miller, J. J. Am. Chem. Soc. 112(), 1990

McClellan, 1963

AUTHOR UNKNOWN, 0

Harrison, Mass Spectrom. Rev. 16(), 1997

AUTHOR UNKNOWN, 0

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 10833028
PubMed | Europe PMC

Suchen in

Google Scholar