Literature DB >> 16603373

Decarboxylation of metastable methyl benzoate molecular ions.

Noémie Dechamps1, Robert Flammang1, Pascal Gerbaux2, Pham-Cam Nam3, Minh-Tho Nguyen3.   

Abstract

By using a combination of mass spectrometric methodologies and density functional theory calculations [DFT/B3LYP/6-311 ++ G(d, p)], it is proposed that the decarboxylation of metastable methyl benzoate molecular ions occurs via distonic and ion-neutral complex (INC) intermediates. The same INC involving a complex between the benzyl radical and protonated carbon dioxide is also generated upon decarboxylation of metastable phenylacetic acid molecular ions. Internal proton transfer within the INC produces in fine a mixture of toluene and isotoluene radical cations.

Entities:  

Year:  2006        PMID： 16603373     DOI： 10.1016/j.jasms.2006.02.015

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN： 1044-0305            Impact factor:   3.109


  2 in total

1.  A ring walk of methylene groups in toluene radical cations. An extension of the toluene-cycloheptatriene rearrangement of aromatic radical cations. Theory and experiment.

Authors:  Hans-Friedrich Grützmacher; Natascha Harting
Journal:  Eur J Mass Spectrom (Chichester)       Date:  2003       Impact factor: 1.067

2.  Reactions of the ionized enol tautomer of acetanilide: elimination of HNCO via a novel rearrangement.

Authors:  Lisa N Heydorn; Lynn M Carter; Richard D Bowen; Johan K Terlouw
Journal:  Eur J Mass Spectrom (Chichester)       Date:  2003       Impact factor: 1.067
  2 in total
  3 in total

1.  Density functional theory and mass spectrometry of phthalate fragmentations mechanisms: modeling hyperconjugated carbocation and radical cation complexes with neutral molecules.

Authors:  Yassin A Jeilani; Beatriz H Cardelino; Victor M Ibeanusi
Journal:  J Am Soc Mass Spectrom       Date:  2011-08-11       Impact factor: 3.109

2.  Ion-neutral complexes resulting from dissociative protonation: fragmentation of alpha-furanylmethyl benzyl ethers and 4-N,N-dimethylbenzyl benzyl ethers.

Authors:  Pengyuan Liu; Nan Hu; Yuanjiang Pan; Yaping Tu
Journal:  J Am Soc Mass Spectrom       Date:  2009-12-28       Impact factor: 3.109

3.  Picosecond to millisecond tracking of a photocatalytic decarboxylation reaction provides direct mechanistic insights.

Authors:  Aditi Bhattacherjee; Mahima Sneha; Luke Lewis-Borrell; Omri Tau; Ian P Clark; Andrew J Orr-Ewing
Journal:  Nat Commun       Date:  2019-11-13       Impact factor: 14.919
  3 in total

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