Copyright © 1985 Published by Elsevier B.V. https://doi.org/10.1016/0301-0104(85)80192-0. In electrospray ionization tandem mass spectrometry of protonated 1-benzoylamines (1-benzoylpiperadine, 1-benzoylmorpholine, and 1-benzoyl-4-methylpiperazine), the dominant fragmentation pathway was amide bond cleavage to form benzoyl cation and neutral amine. View the article PDF and any associated supplements and figures for a period of 48 hours. 14.6a Fragmentation Patterns of Alkanes, Alkenes, and Aromatic Compounds 14.6b Fragmentation Patterns of Alkyl Halides, Alcohols, and Amines 14.6c Fragmentation Patterns of Ketones and Aldehydes 2016 Dec;51(12):1105-1110. doi: 10.1002/jms.3843. Meanwhile, in their fragmentations, an interesting loss of benzaldehyde (106 Da) was observed and identified to derive from hydride transfer reaction between the benzoyl cation and amine. The mass spectrometric experimental results were consistent with the computational results. Useful information is provided by the model, such as on the assignments of mass-spectral peaks of species with common masses, and on the routes by which the smaller fragments are formed. Transferability of input data and branching patterns is found for fragment species common to benzaldehyde and phenol (and benzene) and considered as an important test for the applicability of the phase space model for large classes of MPI fragmentation spectra. A stepwise mechanism for loss of 106 Da (benzene and CO) could be excluded with the aid of deuterium labeling experiment. Lin Wang, Department of Chemistry and Chemical Engineering, Beijing University of Technology, Beijing, China. J Mass Spectrom. In electrospray ionization tandem mass spectrometry of protonated 1‐benzoylamines (1‐benzoylpiperadine, 1‐benzoylmorpholine, and 1‐benzoyl‐4‐methylpiperazine), the dominant fragmentation pathway was amide bond cleavage to form benzoyl cation and neutral amine. Theoretical calculations indicated that hydride transfers from amines (piperadine, morpholine, and 1-methylpiperazine) to benzoyl cation were thermodynamically permitted, and 1-methylpiperazine was the best hydride donor among the 3 amines. Learn about our remote access options, Tea Research Institute, Chinese Academy of Agricultural Sciences, 9 South Meiling Road, Hangzhou, 310008 China, Department of Chemistry, Zhejiang University, Hangzhou, 310027 China. Fragmentation of protonated ketotifen in mass spectrometry. An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, orcid.org/http://orcid.org/0000-0001-7186-9668, orcid.org/http://orcid.org/0000-0002-3918-3399, I have read and accept the Wiley Online Library Terms and Conditions of Use. Use the link below to share a full-text version of this article with your friends and colleagues. Part of the Ph.D Dissertation of JJ. Yang, UCLA, 1984.  |   |  Learn more. Working off-campus? The computed results seem to be in acceptable agreement with experimental data, but often definite conclusions are difficult to obtain, e.g. benzaldehyde M (106) 105 M-1 mz = 77 H O MW = 106. USA.gov. 2006 Sep;41(9):1195-204. doi: 10.1002/jms.1089.  |  The statistical products phase space model is applied to the multiphoton ionization-fragmentation (MPI) of benzaldehyde and phenol. How does a CC double bond cleave in the gas phase? due to uncertainties of molecular data. If you have previously obtained access with your personal account, please log in. Find NCBI SARS-CoV-2 literature, sequence, and clinical content: https://www.ncbi.nlm.nih.gov/sars-cov-2/. and you may need to create a new Wiley Online Library account. J Mass Spectrom. The relative abundance of the iminium cation (relative to the benzoyl cation) in the fragmentation of protonated 1-benzoyl-4-methylpiperazine was higher than that in the fragmentation of the other 2 protonated 1-benzoylamines. Chai Y(1)(2), Shao Y(3), Wang L(4), Wang L(3). Clipboard, Search History, and several other advanced features are temporarily unavailable. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. A stepwise mechanism for loss of 106 Da (benzene and CO) could be excluded with … J Mass Spectrom. Department of Chemistry and Chemical Engineering, Beijing University of Technology, Beijing, 100124 China, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058 China. Keywords: 2013 Apr;48(4):423-9. doi: 10.1002/jms.3162. benzoyl cation; fragmentation mechanism; hydride acceptor; hydride transfer; loss of benzaldehyde. Any queries (other than missing content) should be directed to the corresponding author for the article. Meanwhile, in their fragmentations, an interesting loss of benzaldehyde (106 Da) was observed and identified to derive from hydride transfer reaction between the benzoyl cation and amine. HHS The full text of this article hosted at iucr.org is unavailable due to technical difficulties. The relative abundance of the iminium cation (relative to the benzoyl cation) in the fragmentation of protonated 1‐benzoyl‐4‐methylpiperazine was higher than that in the fragmentation of the other 2 protonated 1‐benzoylamines. Get the latest research from NIH: https://www.nih.gov/coronavirus. Yunfeng Chai, Tea Research Institute, Chinese Academy of Agricultural Sciences, Hangzhou, China. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Theoretical calculations indicated that hydride transfers from amines (piperadine, morpholine, and 1‐methylpiperazine) to benzoyl cation were thermodynamically permitted, and 1‐methylpiperazine was the best hydride donor among the 3 amines. J Mass Spectrom. Get the latest public health information from CDC: https://www.coronavirus.gov. Meanwhile, in their fragmentations, an interesting loss of benzaldehyde (106 Da) was observed and identified to derive from hydride transfer reaction between the benzoyl cation and amine. Mass Spectrometry: Fragmentation Aliphatic Ketones 2-hexanone O MW = 100 M (100) mz = 58 85 M-15 43 M-57 C O O H OCCH3 McLafferty ... fragmentation patterns Loss of Halide NIH If you do not receive an email within 10 minutes, your email address may not be registered, Please check your email for instructions on resetting your password. Results attd disOion Figs- 3 and 4 show computed "single-energy" mass fragmentation patterns at low, intermediate and high excess energies in the parent ions of benzaldehyde and phenol, respectively- Figs- 5 and 6 give comparisons between computed results and experimental results- The computed results shown were obtained by averaging the single-ene ay mass spectra over an energy … By comparing the fragmentations of protonated 1-benzyl-4-methylpiperazine and protonated 1-benzoyl-4-methylpiperazine and the energetics of their hydride transfer reactions, this study revealed that benzoyl cation was a hydride acceptor in the gas phase, but which was weaker than benzyl cation. Ma G, Liu G, Shen S, Chai Y, Yue L, Zhao S, Pan Y. J Mass Spectrom. The mass spectrometric experimental results were consistent with the computational results. Unlimited viewing of the article PDF and any associated supplements and figures. 2018 Mar;53(3):203-213. doi: 10.1002/jms.4053. Competitive benzyl cation transfer and proton transfer: collision-induced mass spectrometric fragmentation of protonated N,N-dibenzylaniline. Dias HJ, Bento MVB, da Silva ÉH, Saturnino-Júnior A, de Oliveira MF, Vessecchi R, Parreira RLT, Crotti AEM. This site needs JavaScript to work properly. Gas-phase fragmentation of the protonated benzyl ester of proline: intramolecular electrophilic substitution versus hydride transfer. Loss of benzaldehyde in the fragmentation of protonated benzoylamines: Benzoyl cation as a hydride acceptor in the gas phase. National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. Benzaldehyde (C 6 H 5 CHO) is een organische verbinding bestaande uit een benzeenring met een aldehydesubstituent.Het is de eenvoudigste aromatische aldehyde en een van de meest gebruikte in de chemische industrie.Bij kamertemperatuur is het een kleurloze vloeistof met een karakteristieke amandelgeur: benzaldehyde is het belangrijkste bestanddeel in de geur van amandelen.

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