Journal of Physical Organic Chemistry

Cover image for Vol. 28 Issue 7

Editor-in-Chief: Luis Echegoyen

Impact Factor: 1.38

ISI Journal Citation Reports © Ranking: 2014: 36/57 (Chemistry Organic); 98/139 (Chemistry Physical)

Online ISSN: 1099-1395

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  1. Experimental survey of the kinetics of acene Diels–Alder reactions

    Brittni A. Qualizza and Jacob W. Ciszek

    Article first published online: 26 JUN 2015 | DOI: 10.1002/poc.3463

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    The rate profiles for pseudo-first-order reactions between tetracene and selected dienophiles. The reactivity ranged roughly two orders of magnitude, from the slowest reacting dienophile (2,3-dichloromaleic anhydride, light blue) to the fastest dienophile (N–methylmaleimide, orange). Other utilized dienophiles included, in order of reactivity, maleic anhydride (navy), tetrafluoro-1,4-benzoquinone (purple), and p-benzoquinone (green).

  2. DFT study of adenine-uracil base pair damage by OH radical

    Xiaofei Liao, Ling Diao, Li Kou, Zhonggao Li, Minjie Li and Wencong Lu

    Article first published online: 26 JUN 2015 | DOI: 10.1002/poc.3465

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    The reactions for dehydrogenation and hydroxylation of A·U base pair are exothermic, and the compounds in water solution are more favorable than those in gas phase. Dehydrogenation at AN6·U site is most probable. Hydroxylation at AH8·U site is most favorable, and hydroxylation at A·UC5 site is more preference than at A·UC6 site, controlled by kinetics factors. The reaction at A·UC5 and A·UC6 sites are hydroxylation > dehydrogenation. The phenomena match well with the results in previous studies.

  3. Mass spectrometric study of the decomposition pathways of canonical amino acids and α-lactones in the gas phase

    Damodar Koirala, Sampath Ranasinghe Kodithuwakkuge and Paul G. Wenthold

    Article first published online: 24 JUN 2015 | DOI: 10.1002/poc.3464

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    The dissociation pathways of gaseous sulfonated phenylalanine are examined using mass spectrometry. Charge-remote fragmentation occurs, giving products analogous to what are found in gas-phase pyrolysis. Dissociation of the canonical (non-zwitterionic) form of the amino acid occurs by loss of ammonia to give an α-lactone, which further dissociates by the loss of carbon monoxide or carbon dioxide. Direct decarboxylation of the amino acid, commonly observed in the solution, does not occur in the gas phase.

  4. The Baeyer-Villiger oxidation versus aromatic ring hydroxylation: competing organic peracid oxidation mechanisms explored by multivariate modelling of designed multi-response experiments

    Cristian Gambarotti and Hans-René Bjørsvik

    Article first published online: 15 JUN 2015 | DOI: 10.1002/poc.3462

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    The peracid oxidation of substituted acetophenones can be switched to pursue direct ring hydroxylation of the benzene ring or Baeyer-Villiger oxygen insertion. The reaction conditions and substituent effects have been investigated.

  5. Kinetic study of the formation reaction of N-chloro-2-oxazolidinone

    Cristina Pastoriza, Juan Manuel Antelo, Francisco Andrés Amoedo and Mercedes Parajó

    Article first published online: 29 MAY 2015 | DOI: 10.1002/poc.3458

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    The rate constants represented in the Brönsted relationship correspond to processes between the neutral species of amine with HOCl, tBuOCl or with NCS. However, the kinetic results presented in this work seem to indicate that an anionic species of the nucleophile with HOCl, tBuOCl or with NCS takes part in the determining step of the reaction rate.