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Gas-phase formation of protonated benzene during collision-induced dissociation of certain protonated mono-substituted aromatic molecules produced in electrospray ionization.
Rapid Commun Mass Spectrom. 2010 Jun 15; 24(11):1707-16.RC

Abstract

Protonated benzene, C(6)H(7) (+), has been studied extensively to understand the structure and energy of a protonated organic molecule in the gas phase. The formation of C(6)H(7) (+) is either through direct protonation of benzene, i.e., chemical ionization, or through fragmentation of certain radical cations produced from electron ionization or photon ionization. We report a novel observation of C(6)H(7) (+) as a product ion formed in the collision-induced dissociation (CID) of protonated benzamide and related molecules produced via electrospray ionization (ESI). The formation of C(6)H(7) (+) from these even-electron precursor ions during the CID process, which has not been previously reported, is proposed to occur from the protonated molecules via a proton migration in a five-membered ring intermediate followed by the cleavage of the mono-substituent C--C bond and concurrent formation of an ion-molecule complex. This unique mechanism has been scrutinized by examining some deuterated molecules and a series of structurally related model compounds. This finding provides a convenient mean to generate C(6)H(7) (+), a reactive intermediate of considerable interest, for further physical or chemical investigation. Further studies indicate that the occurrence of C(6)H(7) (+) in liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) appears to be a rather common phenomenon for many compounds that contain 'benzoyl-type' moieties. Hence, the observation of the C(6)H(7) (+) ion in LC/ESI-MS/MS can be used as an informative fragmentation pathway which should facilitate the identification of a great number of compounds containing the 'benzoyl-type' and similar structural features. These compounds are frequently present in food and pharmaceutical products as leachable impurities that require strict control and rapid elucidation of their identities.

Authors+Show Affiliations

Global Quality Services - Analytical Sciences, Merck & Co. Inc., 1011 Morris Ave, Union, NJ 07083, USA. minli88@yahoo.comNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20486269

Citation

Li, Min, et al. "Gas-phase Formation of Protonated Benzene During Collision-induced Dissociation of Certain Protonated Mono-substituted Aromatic Molecules Produced in Electrospray Ionization." Rapid Communications in Mass Spectrometry : RCM, vol. 24, no. 11, 2010, pp. 1707-16.
Li M, Lin M, Rustum AM. Gas-phase formation of protonated benzene during collision-induced dissociation of certain protonated mono-substituted aromatic molecules produced in electrospray ionization. Rapid Commun Mass Spectrom. 2010;24(11):1707-16.
Li, M., Lin, M., & Rustum, A. M. (2010). Gas-phase formation of protonated benzene during collision-induced dissociation of certain protonated mono-substituted aromatic molecules produced in electrospray ionization. Rapid Communications in Mass Spectrometry : RCM, 24(11), 1707-16. https://doi.org/10.1002/rcm.4569
Li M, Lin M, Rustum AM. Gas-phase Formation of Protonated Benzene During Collision-induced Dissociation of Certain Protonated Mono-substituted Aromatic Molecules Produced in Electrospray Ionization. Rapid Commun Mass Spectrom. 2010 Jun 15;24(11):1707-16. PubMed PMID: 20486269.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gas-phase formation of protonated benzene during collision-induced dissociation of certain protonated mono-substituted aromatic molecules produced in electrospray ionization. AU - Li,Min, AU - Lin,Mingxiang, AU - Rustum,Abu M, PY - 2010/5/21/entrez PY - 2010/5/21/pubmed PY - 2010/8/11/medline SP - 1707 EP - 16 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 24 IS - 11 N2 - Protonated benzene, C(6)H(7) (+), has been studied extensively to understand the structure and energy of a protonated organic molecule in the gas phase. The formation of C(6)H(7) (+) is either through direct protonation of benzene, i.e., chemical ionization, or through fragmentation of certain radical cations produced from electron ionization or photon ionization. We report a novel observation of C(6)H(7) (+) as a product ion formed in the collision-induced dissociation (CID) of protonated benzamide and related molecules produced via electrospray ionization (ESI). The formation of C(6)H(7) (+) from these even-electron precursor ions during the CID process, which has not been previously reported, is proposed to occur from the protonated molecules via a proton migration in a five-membered ring intermediate followed by the cleavage of the mono-substituent C--C bond and concurrent formation of an ion-molecule complex. This unique mechanism has been scrutinized by examining some deuterated molecules and a series of structurally related model compounds. This finding provides a convenient mean to generate C(6)H(7) (+), a reactive intermediate of considerable interest, for further physical or chemical investigation. Further studies indicate that the occurrence of C(6)H(7) (+) in liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) appears to be a rather common phenomenon for many compounds that contain 'benzoyl-type' moieties. Hence, the observation of the C(6)H(7) (+) ion in LC/ESI-MS/MS can be used as an informative fragmentation pathway which should facilitate the identification of a great number of compounds containing the 'benzoyl-type' and similar structural features. These compounds are frequently present in food and pharmaceutical products as leachable impurities that require strict control and rapid elucidation of their identities. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/20486269/Gas_phase_formation_of_protonated_benzene_during_collision_induced_dissociation_of_certain_protonated_mono_substituted_aromatic_molecules_produced_in_electrospray_ionization_ L2 - https://doi.org/10.1002/rcm.4569 DB - PRIME DP - Unbound Medicine ER -
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