Investigations of the fragmentation pathways of benzylpyridinium ions under ESI/MS conditions
Benzylpyridinium ions are often used as 'thermometer ions' in order to evaluate the internal energy distribution of the ions formed in sources of mass spectrometers. However, the detailed fragmentation pathways of these parent ions were not well established. In particular, fragmentation in...
Saved in:
| Published in: | Journal of mass spectrometry. Vol. 44; no. 12; pp. 1668 - 1675 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Chichester, UK
John Wiley & Sons, Ltd
01-12-2009
Wiley Wiley-Blackwell |
| Subjects: | |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | Benzylpyridinium ions are often used as 'thermometer ions' in order to evaluate the internal energy distribution of the ions formed in sources of mass spectrometers. However, the detailed fragmentation pathways of these parent ions were not well established. In particular, fragmentation involving a rearrangement (RR) process may be influencing the simulated distribution curves. In a previous study, we suggested that such RR actually occurred under electrospray ionization/mass spectrometry (ESI/MS) and fast atom bombardment/mass spectrometry (FAB/MS) experiments. Here, we present a systematic study of different substituted benzylpyridinium ions. Theoretical calculations showed that RR fragmentation leading to substituted tropylium ions could occur under 'soft ionization' conditions, such as ESI or FAB. Experimental results obtained under gas-phase reactivity conditions showed that some substituted benzylpiridinium compounds actually undergo RR fragmentations under ESI/MS conditions. Mass-analyzed kinetic experiments were also carried out to gain information on the reaction pathways that actually occur, and these experimental results are in agreement with the reaction pathways theoretically proposed. Copyright © 2009 John Wiley & Sons, Ltd. |
|---|---|
| AbstractList | Benzylpyridinium ions are often used as 'thermometer ions' in order to evaluate the internal energy distribution of the ions formed in sources of mass spectrometers. However, the detailed fragmentation pathways of these parent ions were not well established. In particular, fragmentation involving a rearrangement (RR) process may be influencing the simulated distribution curves. In a previous study, we suggested that such RR actually occurred under electrospray ionization/mass spectrometry (ESI/MS) and fast atom bombardment/mass spectrometry (FAB/MS) experiments. Here, we present a systematic study of different substituted benzylpyridinium ions. Theoretical calculations showed that RR fragmentation leading to substituted tropylium ions could occur under 'soft ionization' conditions, such as ESI or FAB. Experimental results obtained under gas-phase reactivity conditions showed that some substituted benzylpiridinium compounds actually undergo RR fragmentations under ESI/MS conditions. Mass-analyzed kinetic experiments were also carried out to gain information on the reaction pathways that actually occur, and these experimental results are in agreement with the reaction pathways theoretically proposed. Copyright © 2009 John Wiley & Sons, Ltd. Benzylpyridinium ions are often used as 'thermometer ions' in order to evaluate the internal energy distribution of the ions formed in sources of mass spectrometers. However, the detailed fragmentation pathways of these parent ions were not well established. In particular, fragmentation involving a rearrangement (RR) process may be influencing the simulated distribution curves. In a previous study, we suggested that such RR actually occurred under electrospray ionization/mass spectrometry (ESI/MS) and fast atom bombardment/mass spectrometry (FAB/MS) experiments. Here, we present a systematic study of different substituted benzylpyridinium ions. Theoretical calculations showed that RR fragmentation leading to substituted tropylium ions could occur under 'soft ionization' conditions, such as ESI or FAB. Experimental results obtained under gas-phase reactivity conditions showed that some substituted benzylpiridinium compounds actually undergo RR fragmentations under ESI/MS conditions. Mass-analyzed kinetic experiments were also carried out to gain information on the reaction pathways that actually occur, and these experimental results are in agreement with the reaction pathways theoretically proposed. |
| Author | Karoyan, Philippe Fosse, Céline Rochut, Sophie Pepe, Claude Rondeau, David Zins, Emilie-Laure |
| Author_xml | – sequence: 1 fullname: Zins, Emilie-Laure – sequence: 2 fullname: Rondeau, David – sequence: 3 fullname: Karoyan, Philippe – sequence: 4 fullname: Fosse, Céline – sequence: 5 fullname: Rochut, Sophie – sequence: 6 fullname: Pepe, Claude |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22241484$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/19824036$$D View this record in MEDLINE/PubMed https://hal.science/hal-00813433$$DView record in HAL |
| BookMark | eNp90Vtv0zAUAOAIDbELSPwCyAsCHrId24kvj9s0tk4dIJUJXpDlOk7rLXGKnWyEX4_bRt0TPNmyP5-Lz2Gy51pnkuQ1gmMEgE_umnCMKMPPkgMEgmaCc7633jOaFYjl-8lhCHcAIEROXyT7SHCcA6EHyc-JezChswvV2daFtK3SbmnSyqtFY1y3OU1Xqls-qmFzOzfuz1CvBm9L62zfpJtnvSuNTy9mk5ObWapbV9pNuJfJ80rVwbwa16Pk9tPFt_OrbPrlcnJ-Os10gQjOyDyHXGiOcFVUnBLCKyU0LrFSQAsBmjMKuiqM4aAVcIYRAkN1ybTCxZyQo-TjNu5S1XLlbaP8IFtl5dXpVK7PADgiOSEPKNr3W7vy7a8-9i4bG7Spa-VM2wfJCKFCxN-M8sN_ZTSICIYEfaLatyF4U-2qQCDXI5JxROsHONI3Y9R-3pjyCY4zieDdCFTQqo6jcNqGncMY5yjneXTZ1j3a2gz_TCivb2Zj4tHb0JnfO6_8vYzNskJ-_3wpgX-9JmdnhfwR_dutr1Qr1cLHGm5nGBABxBAXmJC_krvANA |
| CitedBy_id | crossref_primary_10_1007_s13361_011_0176_y crossref_primary_10_1007_s13361_017_1835_4 crossref_primary_10_1002_jms_1847 crossref_primary_10_1039_C7NJ01079F crossref_primary_10_1016_j_ijms_2010_10_006 crossref_primary_10_1007_s13361_012_0344_8 crossref_primary_10_1007_s13361_015_1081_6 crossref_primary_10_1007_s13361_017_1693_0 crossref_primary_10_1016_j_jasms_2010_04_006 crossref_primary_10_1021_ac500132j crossref_primary_10_1002_chem_201101790 crossref_primary_10_1021_jasms_0c00200 crossref_primary_10_1007_s13361_014_0936_6 crossref_primary_10_1002_jms_1731 crossref_primary_10_1039_C1OB06020A crossref_primary_10_1007_s44211_023_00419_0 crossref_primary_10_1007_s13361_012_0352_8 crossref_primary_10_1002_cplu_201600526 crossref_primary_10_1021_jz501903b crossref_primary_10_1016_j_ijms_2012_10_016 crossref_primary_10_1002_ejic_201300480 crossref_primary_10_1002_rcm_7581 crossref_primary_10_1002_jms_3162 crossref_primary_10_1002_rcm_6371 crossref_primary_10_1007_s13361_013_0778_7 crossref_primary_10_1016_j_ijms_2014_07_023 crossref_primary_10_1002_rcm_6611 crossref_primary_10_1002_jms_1645 crossref_primary_10_1002_rcm_6899 |
| Cites_doi | 10.1021/j100192a026 10.1021/ja00826a070 10.1021/cr00106a003 10.1016/j.ijms.2007.02.027 10.1021/jp9605818 10.1002/mas.20027 10.1021/ja01012a044 10.1021/ja00839a016 10.1016/S1010-6030(01)00522-6 10.1021/ac020339z 10.1002/jms.773 10.1002/(SICI)1097-0231(19981130)12:22<1673::AID-RCM385>3.0.CO;2-A 10.1021/jp031328s 10.1016/j.ijms.2003.10.010 10.1016/j.ijms.2005.10.016 10.1021/ja00501a024 10.1021/ja00493a021 10.1021/jp002575o 10.1021/j100044a001 10.1021/ja00384a001 10.1016/S1044-0305(96)00212-7 10.1016/S0009-2614(00)00767-3 10.1002/jms.1461 10.1002/(SICI)1096-9888(199605)31:5<445::AID-JMS354>3.0.CO;2-G 10.1016/S0168-1176(97)00036-0 10.1016/j.ijms.2004.11.010 10.1021/ja9609664 10.1021/ja00465a020 10.1021/jp991409h 10.1063/1.1726622 10.1021/jp048058d |
| ContentType | Journal Article |
| Copyright | Copyright © 2009 John Wiley & Sons, Ltd. 2015 INIST-CNRS Copyright 2009 John Wiley & Sons, Ltd. Distributed under a Creative Commons Attribution 4.0 International License |
| Copyright_xml | – notice: Copyright © 2009 John Wiley & Sons, Ltd. – notice: 2015 INIST-CNRS – notice: Copyright 2009 John Wiley & Sons, Ltd. – notice: Distributed under a Creative Commons Attribution 4.0 International License |
| DBID | FBQ BSCLL IQODW NPM AAYXX CITATION 7SR 7U5 8BQ 8FD JG9 L7M 7X8 1XC |
| DOI | 10.1002/jms.1672 |
| DatabaseName | AGRIS Istex Pascal-Francis PubMed CrossRef Engineered Materials Abstracts Solid State and Superconductivity Abstracts METADEX Technology Research Database Materials Research Database Advanced Technologies Database with Aerospace MEDLINE - Academic Hyper Article en Ligne (HAL) |
| DatabaseTitle | PubMed CrossRef Materials Research Database Engineered Materials Abstracts Solid State and Superconductivity Abstracts Technology Research Database Advanced Technologies Database with Aerospace METADEX MEDLINE - Academic |
| DatabaseTitleList | MEDLINE - Academic PubMed Materials Research Database CrossRef |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1096-9888 |
| EndPage | 1675 |
| ExternalDocumentID | oai_HAL_hal_00813433v1 10_1002_jms_1672 19824036 22241484 JMS1672 ark_67375_WNG_08PJ3BB5_X US201301718923 |
| Genre | article Journal Article |
| GroupedDBID | --- -~X .3N .GA .GJ .Y3 05W 0R~ 10A 1L6 1OB 1OC 1ZS 31~ 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5RE 5VS 66C 702 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHHS AANLZ AAONW AASGY AAXRX AAZKR ABCQN ABCUV ABDBF ABEML ABHUG ABIJN ACAHQ ACBWZ ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACPRK ACSCC ACSMX ACXBN ACXME ACXQS ADAWD ADBBV ADDAD ADEOM ADIZJ ADKYN ADMGS ADOZA ADZMN AEEZP AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFRAH AFVGU AFZJQ AGJLS AHMBA AI. AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB AQPKS ASPBG ATUGU AUFTA AVWKF AZBYB AZFZN AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BNHUX BROTX BRXPI BY8 CS3 D-E D-F DCZOG DPXWK DR1 DR2 DRFUL DRSTM DU5 EBD EBS EJD F00 F01 F04 F5P FBQ FEDTE G-S G.N GNP GODZA H.T H.X HBH HF~ HHY HHZ HVGLF HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- P2P P2W P2X P4D PALCI PQQKQ Q.N Q11 QB0 QRW R.K RIWAO RNS ROL RWI RX1 RYL SAMSI SUPJJ TN5 TUS UB1 UQL V2E VH1 W8V W99 WBFHL WBKPD WIB WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XV2 ZCG ZZTAW ~02 ~IA ~KM ~WT AAHBH AHBTC AITYG BSCLL HGLYW OIG WRJ 08R IQODW NPM AAMNL AAYXX CITATION 7SR 7U5 8BQ 8FD JG9 L7M 7X8 1XC |
| ID | FETCH-LOGICAL-c5132-3b4049c812f5f86338fa9c2d2aa06590c8760cf5ee80ca0872110e6cd7ca25b33 |
| IEDL.DBID | 33P |
| ISSN | 1076-5174 1096-9888 |
| IngestDate | Tue Oct 15 15:36:46 EDT 2024 Fri Aug 16 08:47:16 EDT 2024 Sat Aug 17 03:49:52 EDT 2024 Thu Nov 21 22:07:57 EST 2024 Sat Sep 28 07:49:29 EDT 2024 Sun Oct 22 16:08:16 EDT 2023 Sat Aug 24 00:57:29 EDT 2024 Wed Oct 30 09:51:43 EDT 2024 Wed Dec 27 19:17:50 EST 2023 |
| IsDoiOpenAccess | false |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| Keywords | Substituent effect Ion molecule reaction Tandem mass spectrometry Collisional activation Organic cation Theoretical study Fragmentation pattern Experimental study Electrospray DFT calculations benzylpyridinium ions Fast atom bombardment mass spectrometry tropylium ions Density functional method ion/molecule reactions mass spectrometry Gas phase MIKE mass spectrum |
| Language | English |
| License | CC BY 4.0 Copyright 2009 John Wiley & Sons, Ltd. Distributed under a Creative Commons Attribution 4.0 International License: http://creativecommons.org/licenses/by/4.0 |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c5132-3b4049c812f5f86338fa9c2d2aa06590c8760cf5ee80ca0872110e6cd7ca25b33 |
| Notes | http://dx.doi.org/10.1002/jms.1672 ArticleID:JMS1672 istex:A37A1E2BE4E6D165DAFEC8AC6FB0A002473C4EC7 ark:/67375/WNG-08PJ3BB5-X ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-2157-6696 0000-0001-5326-5916 |
| OpenAccessLink | https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/jms.1672 |
| PMID | 19824036 |
| PQID | 1671397196 |
| PQPubID | 23500 |
| PageCount | 8 |
| ParticipantIDs | hal_primary_oai_HAL_hal_00813433v1 proquest_miscellaneous_733699167 proquest_miscellaneous_1671397196 crossref_primary_10_1002_jms_1672 pubmed_primary_19824036 pascalfrancis_primary_22241484 wiley_primary_10_1002_jms_1672_JMS1672 istex_primary_ark_67375_WNG_08PJ3BB5_X fao_agris_US201301718923 |
| PublicationCentury | 2000 |
| PublicationDate | December 2009 |
| PublicationDateYYYYMMDD | 2009-12-01 |
| PublicationDate_xml | – month: 12 year: 2009 text: December 2009 |
| PublicationDecade | 2000 |
| PublicationPlace | Chichester, UK |
| PublicationPlace_xml | – name: Chichester, UK – name: Chichester – name: England |
| PublicationTitle | Journal of mass spectrometry. |
| PublicationTitleAlternate | J. Mass Spectrom |
| PublicationYear | 2009 |
| Publisher | John Wiley & Sons, Ltd Wiley Wiley-Blackwell |
| Publisher_xml | – name: John Wiley & Sons, Ltd – name: Wiley – name: Wiley-Blackwell |
| References | P. Ausloos. Structure and izomerization of C7H7+ ions formed in the charged-transfer-induced fragmentation of ethylbenzene, toluene and norbornadiene. Journal of the American Society 1982, 104, 5259. J. Naban-Maillet, D. Lesage, A. Bossée, Y. Guimbert, J. Sztaray, K. Vekey, J. C. Tabet. Internal energy distribution in electrospray ionization. Journal of Mass Spectrometry 2005, 40, 1. R. C. Dunbar. Nature of the C7H7+ ions from toluene parent ion phototdissociation. Journal of the American Society 1975, 97(6), 1382. D. Fati, A. J. Lorquet, R. Locht, J. C. Lorquet, B. Ley. Kinetic energy release distribution for tropylium and benzylium ion formation from the toluene cation. Journal of Physical Chemistry A 2004, 108, 9777. I. S. Ignatyev, T. Sundius. Competitive ring hydride shifts and tolyl-benzyl rearrangements in tolyl and silatolyl cations. Chemical Physics Letters 2000, 326, 101. C. Heinemann, D. Schröder, H. Schwarz. Generation of the thermochemically stable dications AlF2+ and SiF2+ via charge-stripping mass spectrometry. Journal of Physical Chemistry 1995, 99, 16195. A. Hoxha, C. Collette, E. De Pauw, B. Leyh. Mechanism of collisional heating in electrospray mass spectrometry: ion trajectory calculations. Journal of Physical Chemistry A 2001, 105, 7326. C. Collette, L. Drahos, E. De Pauw, K. Vekey. Comparison of the internal energy distributions of ions produced by different electrospray sources. Rapid Communications in Mass Spectrometry 1998, 12, 1673. V. Gabelica, E. De Pauw. Internal energy and fragmentation of ions produced in electrospray sources. Mass Spectrometry Reviews 2005, 24, 566. G. Luo, I. Marginean, A. Vertes. Internal energy of ions generated by matrix-assisted laser desorption/ionization. Analytical Chemistry 2002, 74, 6185. A. Nicolaides, L. Radom. Relative stabilities and hydride affinities of silatropylium and silabenzyl cations and their isomers. Comparison with the carbon analogues tropylium and benzylium cations. Journal of the American Society 1996, 118, 10561. I. Oref, D. C. Tardy. Energy transfer in highly excited large polyatomic molecules. Chemical Reviews 1990, 90, 1407. I. Kretzschmar, D. Schröder, H. Schwarz. The tropylium/benzylium ion dichotomy in the gas-phase reactions of transition metal chacogenide cations with toluene. International Journal of Mass Spectrometry and Ion Processes 1997, 167/168, 103. P. Milko, J. Roithova, D. Schröder, H. Schwarz. Doubly protonated A, 3, 5-trimethylenebenzene (C9H$_{11}^{2+}$) and homologous C7H$_{7}^{2+}$ and C8H$_{9}^{2+}$ dictations: structures and unimolecular fragmentation patterns. International Journal of Mass Spectrometry 2007, 267, 1397. J. C. Choe. Loss of benzene from methylphenylsilane and dimethylphenylsilane molecular cations. International Journal of Mass Spectrometry 2005, 242, 5. E. L. Zins, C. Pepe, D. Schröder. Selectivites and internal-energy effects in the methylene-transfer reactions of substituted benzylium/tropylium ions with neutral toluene. Faraday Discuss 2009, (in press). S. Schulze, A. Paul, K. M. Weitzel. Formation of C7H$_{7}^{+}$ ions from ethylbenzene and o-xylene ions: fragmentation vs isomerization. International Journal of Mass Spectrometry 2006, 252, 189. J. H. Moon, J. C. Choe, M. S. Kim. Kinetic energy release distribution in the dissociation of toluene molecular ion. The tropylium vs benzylium story continues. Journal of Physical Chemistry A 2004, 104, 458. F. W. McLafferty, F. M. Bockhoff. Formation of benzyl and tropylium ions from gazeous toluene and cycloheptatriene cations. Journal of the American Society 1979, 101(7), 1783. T. D. Fridgen, J. Troe, A. A. Viggiano, A. J. Midey, S. Williams, T. B. McMahon. Experimental and theoretical studies of the Benzylium+/Tropylium+ ratios after charge transfer to ethylbenzenes. Journal of Physical Chemistry 2004, 108, 5600. V. Gabelica, E. De Pauw, M. Karas. Influence of the capillary temperature and the source pressure on the internal energy distribution of electrosprayed ions. International Journal of Mass Spectrometry 2004, 231, 189. T. Ast, M. Medved, J. Marsel. Ion kinetic energy spectroscopy study of doubly charged ion reactions in some mono and disubstituted benzenes. Croatica Chemica Acta 1977, 24, 425. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. StratmannJr, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople. Gaussian 03. Gaussian, Inc: Pittsburgh, 2002. P. Brown. Occurence and timing of the rearrangement of benzyl ions to tropylium ions in the mass spectra of substituted benzyl phenyl ethers. Journal of the American Society 1968, 90(10), 2694. K. Vekey. Internal energy effects in mass spectrometry. Journal of Mass Spectrometry 1996, 31, 445. J. V. B. Oriedo, D. H. Russell. Gas-phase ion molecule charge-exchange reactions of Fe+ with Fe(CO)5-observation of higher lying metastable electronic states. Journal of. Physical Chemistry 1992, 96, 5314. K. R. Jenning, J. H. Futrell. Decomposition of tropylium and substituted tropylium ions. Journal of Physical Chemistry 1966, 44, 4315. E. L. Zins, C. Pepe, D. Rondeau, S. Rochut, N. Galland, J. C. Tabet. Theoretical and experimental study of thropylium formation form substituted benzylpyridinium species. Journal of Mass Spectrometry 2009, 44, 12. D. M. Shold, P. Ausloos. Structures of butyl ions formed by electron impact ionization of isomeric butyl halides and alkanes. Journal of the American Society 1978, 100(25), 7915. V. A. Kharlanov, W. Abraham, W. Rettig. Photophysics of arylsubstituted tropylium ions. Journal of Photochemistry and Photobiology A: Chemistry 2001, 143, 109. T. Baer, P. M. Mayer. Statistical Rice-Ramsperger-Kassel-Marcus quasiequilibrium theory calculations in mass spectrometry. Journal of theAmerican Society for Mass Spectrometry 1997, 8, 103. J. Shen, R. C. Dunbar, G. A. Olah. Gas phase benzyl cations from toluene precursors. Journal of the American Society 1974, 96(19), 6227. S. T. Oh, J. C. Choe, M. S. Kim. Photodissociation dynamics of n-butylbenzene molecular ion. Journal of Physical Chemistry 1996, 100, 13367. J. A. A. Jackson, S. G. Lias, P. Ausloos. An ion cyclotron resonance study of the structures of C7H7+ ions. Journal of the American Society 1977, 99, 7515. 2009; 44 2001; 143 2007; 267 2004; 104 1979; 101 2002; 74 1974; 96 1995; 99 2005; 40 2009 2006; 252 1975; 97 1982; 104 1996; 100 1977; 24 2002 2004; 108 1996; 31 2005; 24 1992; 96 2001; 105 1997; 8 2004; 231 2005; 242 2000; 326 1978; 100 1968; 90 1977; 99 1990; 90 1966; 44 1998; 12 1996; 118 1997; 167/168 e_1_2_5_27_2 Ast T. (e_1_2_5_25_2) 1977; 24 e_1_2_5_22_2 e_1_2_5_23_2 Milko P. (e_1_2_5_29_2) 2007; 267 e_1_2_5_20_2 e_1_2_5_21_2 Dunbar R. C. (e_1_2_5_19_2) 1975; 97 Shold D. M. (e_1_2_5_16_2) 1978; 100 e_1_2_5_28_2 Zins E. L. (e_1_2_5_14_2) 2009 McLafferty F. W. (e_1_2_5_17_2) 1979; 101 Moon J. H. (e_1_2_5_24_2) 2004; 104 Jenning K. R. (e_1_2_5_26_2) 1966; 44 e_1_2_5_13_2 e_1_2_5_9_2 e_1_2_5_35_2 e_1_2_5_8_2 e_1_2_5_7_2 e_1_2_5_10_2 e_1_2_5_33_2 e_1_2_5_6_2 e_1_2_5_5_2 e_1_2_5_12_2 e_1_2_5_31_2 e_1_2_5_4_2 e_1_2_5_11_2 e_1_2_5_32_2 e_1_2_5_3_2 e_1_2_5_2_2 Frisch M. J. (e_1_2_5_34_2) 2002 Shen J. (e_1_2_5_15_2) 1974; 96 Brown P. (e_1_2_5_18_2) 1968; 90 e_1_2_5_30_2 |
| References_xml | – volume: 104 start-page: 5259 year: 1982 article-title: Structure and izomerization of C7H7+ ions formed in the charged‐transfer‐induced fragmentation of ethylbenzene, toluene and norbornadiene publication-title: Journal of the American Society – volume: 12 start-page: 1673 year: 1998 article-title: Comparison of the internal energy distributions of ions produced by different electrospray sources publication-title: Rapid Communications in Mass Spectrometry – volume: 74 start-page: 6185 year: 2002 article-title: Internal energy of ions generated by matrix‐assisted laser desorption/ionization publication-title: Analytical Chemistry – volume: 90 start-page: 2694 issue: 10 year: 1968 article-title: Occurence and timing of the rearrangement of benzyl ions to tropylium ions in the mass spectra of substituted benzyl phenyl ethers publication-title: Journal of the American Society – volume: 143 start-page: 109 year: 2001 article-title: Photophysics of arylsubstituted tropylium ions publication-title: Journal of Photochemistry and Photobiology A: Chemistry – volume: 101 start-page: 1783 issue: 7 year: 1979 article-title: Formation of benzyl and tropylium ions from gazeous toluene and cycloheptatriene cations publication-title: Journal of the American Society – volume: 105 start-page: 7326 year: 2001 article-title: Mechanism of collisional heating in electrospray mass spectrometry: ion trajectory calculations publication-title: Journal of Physical Chemistry A – volume: 96 start-page: 6227 issue: 19 year: 1974 article-title: Gas phase benzyl cations from toluene precursors publication-title: Journal of the American Society – volume: 267 start-page: 1397 year: 2007 article-title: Doubly protonated A, 3, 5‐trimethylenebenzene (C H ) and homologous C H and C H dictations: structures and unimolecular fragmentation patterns publication-title: International Journal of Mass Spectrometry – volume: 326 start-page: 101 year: 2000 article-title: Competitive ring hydride shifts and tolyl‐benzyl rearrangements in tolyl and silatolyl cations publication-title: Chemical Physics Letters – volume: 242 start-page: 5 year: 2005 article-title: Loss of benzene from methylphenylsilane and dimethylphenylsilane molecular cations publication-title: International Journal of Mass Spectrometry – volume: 24 start-page: 566 year: 2005 article-title: Internal energy and fragmentation of ions produced in electrospray sources publication-title: Mass Spectrometry Reviews – volume: 44 start-page: 12 year: 2009 article-title: Theoretical and experimental study of thropylium formation form substituted benzylpyridinium species publication-title: Journal of Mass Spectrometry – volume: 8 start-page: 103 year: 1997 article-title: Statistical Rice‐Ramsperger‐Kassel‐Marcus quasiequilibrium theory calculations in mass spectrometry publication-title: Journal of theAmerican Society for Mass Spectrometry – volume: 24 start-page: 425 year: 1977 article-title: Ion kinetic energy spectroscopy study of doubly charged ion reactions in some mono and disubstituted benzenes publication-title: Croatica Chemica Acta – volume: 108 start-page: 5600 year: 2004 article-title: Experimental and theoretical studies of the Benzylium+/Tropylium+ ratios after charge transfer to ethylbenzenes publication-title: Journal of Physical Chemistry – volume: 108 start-page: 9777 year: 2004 article-title: Kinetic energy release distribution for tropylium and benzylium ion formation from the toluene cation publication-title: Journal of Physical Chemistry A – volume: 44 start-page: 4315 year: 1966 article-title: Decomposition of tropylium and substituted tropylium ions publication-title: Journal of Physical Chemistry – volume: 96 start-page: 5314 year: 1992 article-title: Gas‐phase ion molecule charge‐exchange reactions of Fe+ with Fe(CO)5—observation of higher lying metastable electronic states publication-title: Journal of. Physical Chemistry – volume: 252 start-page: 189 year: 2006 article-title: Formation of C H ions from ethylbenzene and o‐xylene ions: fragmentation vs isomerization publication-title: International Journal of Mass Spectrometry – volume: 31 start-page: 445 year: 1996 article-title: Internal energy effects in mass spectrometry publication-title: Journal of Mass Spectrometry – volume: 100 start-page: 13367 year: 1996 article-title: Photodissociation dynamics of n‐butylbenzene molecular ion publication-title: Journal of Physical Chemistry – volume: 99 start-page: 16195 year: 1995 article-title: Generation of the thermochemically stable dications AlF2+ and SiF2+ via charge‐stripping mass spectrometry publication-title: Journal of Physical Chemistry – year: 2002 – volume: 100 start-page: 7915 issue: 25 year: 1978 article-title: Structures of butyl ions formed by electron impact ionization of isomeric butyl halides and alkanes publication-title: Journal of the American Society – volume: 104 start-page: 458 year: 2004 article-title: Kinetic energy release distribution in the dissociation of toluene molecular ion. The tropylium vs benzylium story continues publication-title: Journal of Physical Chemistry A – volume: 97 start-page: 1382 issue: 6 year: 1975 article-title: Nature of the C7H7+ ions from toluene parent ion phototdissociation publication-title: Journal of the American Society – volume: 90 start-page: 1407 year: 1990 article-title: Energy transfer in highly excited large polyatomic molecules publication-title: Chemical Reviews – volume: 167/168 start-page: 103 year: 1997 article-title: The tropylium/benzylium ion dichotomy in the gas‐phase reactions of transition metal chacogenide cations with toluene publication-title: International Journal of Mass Spectrometry and Ion Processes – volume: 231 start-page: 189 year: 2004 article-title: Influence of the capillary temperature and the source pressure on the internal energy distribution of electrosprayed ions publication-title: International Journal of Mass Spectrometry – year: 2009 article-title: Selectivites and internal‐energy effects in the methylene‐transfer reactions of substituted benzylium/tropylium ions with neutral toluene publication-title: Faraday Discuss – volume: 99 start-page: 7515 year: 1977 article-title: An ion cyclotron resonance study of the structures of C7H7+ ions publication-title: Journal of the American Society – volume: 40 start-page: 1 year: 2005 article-title: Internal energy distribution in electrospray ionization publication-title: Journal of Mass Spectrometry – volume: 118 start-page: 10561 year: 1996 article-title: Relative stabilities and hydride affinities of silatropylium and silabenzyl cations and their isomers. Comparison with the carbon analogues tropylium and benzylium cations publication-title: Journal of the American Society – ident: e_1_2_5_2_2 doi: 10.1021/j100192a026 – volume: 96 start-page: 6227 issue: 19 year: 1974 ident: e_1_2_5_15_2 article-title: Gas phase benzyl cations from toluene precursors publication-title: Journal of the American Society doi: 10.1021/ja00826a070 contributor: fullname: Shen J. – ident: e_1_2_5_10_2 doi: 10.1021/cr00106a003 – volume: 267 start-page: 1397 year: 2007 ident: e_1_2_5_29_2 article-title: Doubly protonated A, 3, 5‐trimethylenebenzene (C9H$_{11}^{2+}$) and homologous C7H$_{7}^{2+}$ and C8H$_{9}^{2+}$ dictations: structures and unimolecular fragmentation patterns publication-title: International Journal of Mass Spectrometry doi: 10.1016/j.ijms.2007.02.027 contributor: fullname: Milko P. – ident: e_1_2_5_32_2 doi: 10.1021/jp9605818 – ident: e_1_2_5_4_2 doi: 10.1002/mas.20027 – volume: 90 start-page: 2694 issue: 10 year: 1968 ident: e_1_2_5_18_2 article-title: Occurence and timing of the rearrangement of benzyl ions to tropylium ions in the mass spectra of substituted benzyl phenyl ethers publication-title: Journal of the American Society doi: 10.1021/ja01012a044 contributor: fullname: Brown P. – volume: 97 start-page: 1382 issue: 6 year: 1975 ident: e_1_2_5_19_2 article-title: Nature of the C7H7+ ions from toluene parent ion phototdissociation publication-title: Journal of the American Society doi: 10.1021/ja00839a016 contributor: fullname: Dunbar R. C. – ident: e_1_2_5_23_2 doi: 10.1016/S1010-6030(01)00522-6 – ident: e_1_2_5_11_2 doi: 10.1021/ac020339z – ident: e_1_2_5_5_2 doi: 10.1002/jms.773 – ident: e_1_2_5_7_2 doi: 10.1002/(SICI)1097-0231(19981130)12:22<1673::AID-RCM385>3.0.CO;2-A – ident: e_1_2_5_22_2 doi: 10.1021/jp031328s – ident: e_1_2_5_12_2 doi: 10.1016/j.ijms.2003.10.010 – volume: 24 start-page: 425 year: 1977 ident: e_1_2_5_25_2 article-title: Ion kinetic energy spectroscopy study of doubly charged ion reactions in some mono and disubstituted benzenes publication-title: Croatica Chemica Acta contributor: fullname: Ast T. – ident: e_1_2_5_31_2 doi: 10.1016/j.ijms.2005.10.016 – volume-title: Gaussian 03 year: 2002 ident: e_1_2_5_34_2 contributor: fullname: Frisch M. J. – volume: 101 start-page: 1783 issue: 7 year: 1979 ident: e_1_2_5_17_2 article-title: Formation of benzyl and tropylium ions from gazeous toluene and cycloheptatriene cations publication-title: Journal of the American Society doi: 10.1021/ja00501a024 contributor: fullname: McLafferty F. W. – volume: 100 start-page: 7915 issue: 25 year: 1978 ident: e_1_2_5_16_2 article-title: Structures of butyl ions formed by electron impact ionization of isomeric butyl halides and alkanes publication-title: Journal of the American Society doi: 10.1021/ja00493a021 contributor: fullname: Shold D. M. – ident: e_1_2_5_6_2 doi: 10.1021/jp002575o – year: 2009 ident: e_1_2_5_14_2 article-title: Selectivites and internal‐energy effects in the methylene‐transfer reactions of substituted benzylium/tropylium ions with neutral toluene publication-title: Faraday Discuss contributor: fullname: Zins E. L. – ident: e_1_2_5_3_2 doi: 10.1021/j100044a001 – ident: e_1_2_5_20_2 doi: 10.1021/ja00384a001 – ident: e_1_2_5_9_2 doi: 10.1016/S1044-0305(96)00212-7 – ident: e_1_2_5_35_2 doi: 10.1016/S0009-2614(00)00767-3 – ident: e_1_2_5_13_2 doi: 10.1002/jms.1461 – ident: e_1_2_5_8_2 doi: 10.1002/(SICI)1096-9888(199605)31:5<445::AID-JMS354>3.0.CO;2-G – ident: e_1_2_5_27_2 doi: 10.1016/S0168-1176(97)00036-0 – ident: e_1_2_5_30_2 doi: 10.1016/j.ijms.2004.11.010 – ident: e_1_2_5_28_2 doi: 10.1021/ja9609664 – ident: e_1_2_5_21_2 doi: 10.1021/ja00465a020 – volume: 104 start-page: 458 year: 2004 ident: e_1_2_5_24_2 article-title: Kinetic energy release distribution in the dissociation of toluene molecular ion. The tropylium vs benzylium story continues publication-title: Journal of Physical Chemistry A doi: 10.1021/jp991409h contributor: fullname: Moon J. H. – volume: 44 start-page: 4315 year: 1966 ident: e_1_2_5_26_2 article-title: Decomposition of tropylium and substituted tropylium ions publication-title: Journal of Physical Chemistry doi: 10.1063/1.1726622 contributor: fullname: Jenning K. R. – ident: e_1_2_5_33_2 doi: 10.1021/jp048058d |
| SSID | ssj0009946 |
| Score | 2.138108 |
| Snippet | Benzylpyridinium ions are often used as 'thermometer ions' in order to evaluate the internal energy distribution of the ions formed in sources of mass... Benzylpyridinium ions are often used as ‘thermometer ions’ in order to evaluate the internal energy distribution of the ions formed in sources of mass... |
| SourceID | hal proquest crossref pubmed pascalfrancis wiley istex fao |
| SourceType | Open Access Repository Aggregation Database Index Database Publisher |
| StartPage | 1668 |
| SubjectTerms | benzylpyridinium ions Bombardment Chemical Sciences Chemistry DFT calculations Exact sciences and technology Fragmentation Internal energy ion/molecule reactions Ionization Mass spectrometers Mass spectrometry Mathematical analysis Organic chemistry Pathways Reactivity and mechanisms tropylium ions |
| Title | Investigations of the fragmentation pathways of benzylpyridinium ions under ESI/MS conditions |
| URI | https://api.istex.fr/ark:/67375/WNG-08PJ3BB5-X/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fjms.1672 https://www.ncbi.nlm.nih.gov/pubmed/19824036 https://search.proquest.com/docview/1671397196 https://search.proquest.com/docview/733699167 https://hal.science/hal-00813433 |
| Volume | 44 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3fb9MwED6x8QAv_GbLxiaD0N5CE9tpEt620VEmNk0KE3tBluPYY7CmU0sH5a_fndO0VGISEi-t1Poq5-58_q72fQfw2smuzrPYhCZKTSi5kWEmkxiXu0stWcV52sV-kR6fZe96RJPztq2Fafgh5n-40crw8ZoWuC7HnQVp6LfB-E3cTSn8YpLgqzfEyYJvN28KizBND4mMueWdjXinFVzaiVacHuLrV7oNeZcU_ItuSeoxKso1HS7-BkGXEa3fkg4e_s_DPIIHMyDKdhvPeQx3bP0E7u23_d-ewpc_KDjQNdnQMQSLDOd5PpgVLNWMGhr_1FP_bWnr39PLq-noAvfDi8mAeTEqUhuxXvGhc1QwTL6r5o7YMzg96H3a74ezZgyhSTBjDUUpMZkwiAdc4rIuZrZO54ZXXGs6mo0MhtXIuMTaLDI6ynxmabumSo3mSSnEc1ith7VdB1aWWvLK6txVdE4sSlGlKFVp_JXUyiiAl61h1FXDuaEadmWuUFGKFBXAOlpM6XMMheq04HQAG-M-i3g1gFdoxrkk8Wf3dz8q-owAkJBCXMcB7Hgrz4fp0Xe645Ym6vPxexVlJ4diby9RZwFsL7nBXIAT-JGZxNm2fqHQQnTeoms7nPh5Er7GGBcAu2UMsVESRE8DWGt8avHIeUZkiSi8413nVl2ow6OC3jf-deAm3OezNhhR_AJWf4wmdgtWxtVk26-iG04sGuU |
| link.rule.ids | 230,315,782,786,887,1408,27933,27934,46064,46488 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3db9MwED-x7WG88A0LHyMgtLfQxHa-xNM2OrrRVpO6ib0gy3HssY2mU0uB8tdz5zQtlZiExEsjNb7I8Z3Pv4t9vwN4Y0Wi8izSgQ5THQimRZCJOMLpblNDWrGOdrEzSPtn2fs20eS8a3Jhan6IxQc3mhnOX9MEpw_SrSVr6OVw8jZKUvS_GyJBO6T8DX68ZNzN69QiDNQDomNumGdD1mokV9aiNatG-PuFzkNu0BD_pHOSaoJDZesaF38DoauY1i1KB3f_63XuwZ05FvV3a-O5D7dM9QA295sScA_h8x8sHGid_sj6iBd97Oj5cJ6zVPlU0_iHmrm7hal-zb5ez8YXuCReTIe-E6M8tbHfHhy2egMf4--yPib2CE4P2if7nWBejyHQMQatAS8ExhMaIYGNbZZgcGtVrlnJlKLd2VCjZw21jY3JQq3CzAWXJtFlqhWLC84fw3o1qswW-EWhBCuNym1JW8W84GWKUqXCp6RGhB68ajQjr2vaDVkTLDOJAyVpoDzYQpVJdY7eUJ4OGO3BRrjUImT14DXqcSFJFNqd3a6k_wgDccH598iDHafmRTM1vqJjbmksP_U_yDA7PuJ7e7E882B7xQ4WAozwj8gE9rYxDIkaoi0XVZnR1PWTIDa6OQ_8G9oQISWh9NSDJ7VRLV85z4gvEYV3nO3cOBbyqDeg69N_bfgSNjsnva7sHvY_PoPbbF4VI4yew_q38dS8gLVJOd12U-o3HXAfDQ |
| linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3db9MwED-xTQJe-IaFj2EQ2ltoEjtNwts-WrqxVZXCxF6Q5Tj2GNC0ailQ_nrunKalEpOQeEml1FfZd-fz72r7dwCvrGirLA21r4NE-yLSwk9FHOJ0t4khq1hHu9jLk_55etghmpw3zV2Ymh9i-YcbzQwXr2mCj0vbWpGGfh5OX4ftBMPvlkAUTrz5nA9WhLtZfbMI83Sf2Jgb4tkgajWSa0vRhlUjfH6i45BbpOGfdExSTVFTti5x8TcMug5p3ZrUvf0_o7kDtxZIlO3VrnMXrpnqHtw4aArA3YePf3BwoG-ykWWIFhn282K4uLFUMapo_EPN3beFqX7Nv47nk0tcEC9nQ-bE6JbahHXyo9ZpzjD7LutDYg_grNt5f9DzF9UYfB1jyurzQmA2oREQ2NimbUxtrcp0VEZK0d5soDGuBtrGxqSBVkHqUkvT1mWiVRQXnD-EzWpUmW1gRaFEVBqV2ZI2innBywSlSoW_khgRePCiMYwc16QbsqZXjiQqSpKiPNhGi0l1gbFQnuUR7cCGuNAiYPXgJZpxKUkE2r29E0nvCAFxwfn30INdZ-VlMzX5Qofcklh-6L-VQTo45vv7sTz3YGfNDZYCEaEfkQrsbeMXEi1EGy6qMqOZ6ycBbAxyHrAr2hAdJWH0xINHtU-thpylxJaIwrvOda7UhTw-zenz8b82fA7XB4ddeXLUf_cEbkaLkhhB-BQ2v01m5hlsTMvZjptQvwGEOR2z |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Investigations+of+the+fragmentation+pathways+of+benzylpyridinium+ions+under+ESI%2FMS+conditions&rft.jtitle=Journal+of+mass+spectrometry.&rft.au=Zins%2C+Emilie%E2%80%90Laure&rft.au=Rondeau%2C+David&rft.au=Karoyan%2C+Philippe&rft.au=Fosse%2C+C%C3%A9line&rft.date=2009-12-01&rft.pub=John+Wiley+%26+Sons%2C+Ltd&rft.issn=1076-5174&rft.eissn=1096-9888&rft.volume=44&rft.issue=12&rft.spage=1668&rft.epage=1675&rft_id=info:doi/10.1002%2Fjms.1672&rft.externalDBID=10.1002%252Fjms.1672&rft.externalDocID=JMS1672 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1076-5174&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1076-5174&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1076-5174&client=summon |