Journal of Physical Organic Chemistry

Cover image for Vol. 26 Issue 6

June 2013

Volume 26, Issue 6

Pages i–iii, 451–523

  1. Issue Information

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Review
    5. Research Articles
    6. Letter to the Editor
    1. Issue Information (pages i–iii)

      Article first published online: 22 MAY 2013 | DOI: 10.1002/poc.3038

  2. Early Excellence Profiles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Review
    5. Research Articles
    6. Letter to the Editor
  3. Review

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Review
    5. Research Articles
    6. Letter to the Editor
    1. Dihydrogen bond and X–H…σ interaction as sub-classes of hydrogen bond (pages 452–459)

      Sławomir J. Grabowski

      Article first published online: 30 APR 2013 | DOI: 10.1002/poc.3109

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      Dihydrogen bond (DHB) and X–H…σinteraction are compared; both possess numerous characteristics of the hydrogen bond. The NBO method shows that σ [RIGHTWARDS ARROW] σ* is the most important interaction connected with the electron charge transfer from the Lewis base to the Lewis acid for DHB as well as for the X–H…σ hydrogen bond. However QTAIM and the decomposition of the energy of interaction show that there are distinct differences between these interactions. The X–H…π hydrogen bond is also discussed since it possesses few characteristics typical for the X–H…σ interaction and not for the dihydrogen bond.

  4. Research Articles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Review
    5. Research Articles
    6. Letter to the Editor
    1. Electronic effect of ionic-pair substituents (pages 460–466)

      Hang Chen, Lu Jia, Xuan Xu, Jianyong Mao, Yong Wang, Congmin Wang and Haoran Li

      Article first published online: 24 MAR 2013 | DOI: 10.1002/poc.3108

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      The para Hammett constants of 89 different ionic-pair substituents (77 anion-cationic and 12 cation-anionic) were calculated in the gas phase based on the density functional theory. Some of them were checked by the 13C NMR method. The results show that both the anion-cationic and cation-anionic substituents are electron withdrawing groups and the different cation-anion combinations could tune the Hammett constants of the ionic-pair substituents in a range from 0.03 to 0.77.

    2. Additivity of substituent effects on the acidity of alcohols (pages 467–472)

      José-Luis M. Abboud, Ilmar A. Koppel and Ivar Koppel

      Article first published online: 1 APR 2013 | DOI: 10.1002/poc.3110

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      The gas-phase acidity of new alcohols was determined by FT-ICR. These and other data were studied computationally

    3. The geometry and electronic structure of Aristolochic acid: possible implications for a frozen resonance (pages 473–483)

      Sergio Manzetti and Tian Lu

      Article first published online: 8 MAY 2013 | DOI: 10.1002/poc.3111

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      The electronic structure of Aristolochic acid (AA1) has been elucidated using the aug-cc-pVDZ level of theory, resulting in a potentially trapped resonance at the ring A which causes a localized electronic distribution, differentiating the first from the two other rings of the phenanthrene moiety of AA1. This property can play a significant role in its transformation pathways in biochemical and toxicological settings.

    4. Computational study of pyrazine-based derivatives and their N-oxides as high energy materials (pages 484–491)

      He Lin, Peng-Yuan Chen, Shun-Guan Zhu, Lin Zhang, Xin-Hua Peng and Hong-Zhen Li

      Article first published online: 4 APR 2013 | DOI: 10.1002/poc.3113

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      High energy density materials (HEDMs) have been widely used for military and civil applications. However, current HEDMs cannot meet the increasing requirements. It is well-known that pyrazine derivatives are promising potential candidates of HEDMs. In this work, three series of pyrazine derivatives containing three heterocycles have been designed and theoretically investigated. Calculations show that these compounds have high positive heats of formation, powerful detonation properties and thermal stability.

    5. To what extent can a conjugation between two pairs of peri-nitro and peri-amino groups be realized through the naphthalene core? (pages 492–502)

      Valery A. Ozeryanskii, Ekaterina A. Filatova, Alexander F. Pozharskii, Dmitrii A. Shevchuk and Vladimir I. Sorokin

      Article first published online: 6 MAY 2013 | DOI: 10.1002/poc.3114

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      For the first time, modified NH2 groups (N-acylated, N-alkylated, N,N′-bridged, N-heterocyclic, and N-deprotonated) were ranged with regard to their electron-donating ability from the naphthalene peri-positions to the conjugated NO2 groups in dimethyl sulfoxide solution and in the solid state.

    6. Kinetics and mechanism of the reaction of alkoxymethylidene malonate and malononitrile with hydrazines and anilines (pages 503–509)

      Denisa Tarabová, Viktor Milata and Jiří Hanusek

      Article first published online: 26 APR 2013 | DOI: 10.1002/poc.3115

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      The kinetics and mechanism of the nucleophilic vinylic substitution of dialkyl (alkoxymethylidene)malonates (1a,b) and (ethoxymethylidene)malononitrile (1c) with substituted hydrazines and anilines were studied at 25 °C in methanol. The reactions showed overall second-order and third-order kinetics with hydrazines and anilines, respectively. Brønsted and Hammett plots obtained from the measured data reflected gradually increasing order of the C−N bond formed in the transition state with the increasing reactivity of and with the change from hydrazines to anilines.

    7. Dimer radical cation of 4-thiouracil: a pulse radiolysis and theoretical study (pages 510–516)

      K. P. Prasanthkumar, Cherumuttathu H. Suresh and C. T. Aravindakumar

      Article first published online: 30 APR 2013 | DOI: 10.1002/poc.3116

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      The transient produced upon one-electron oxidation of 4-thiouracil by hydroxyl radical has been investigated by means of nanosecond pulse radiolysis/optical absorption technique. The transient is assigned as a dimer radical cation characterized by a two-center-three-electron sulfur–sulfur bond, and the results are supported by density functional theory calculations.

    8. Theoretical studies on [2 + 2 + 2] reaction mechanisms of three ethynes. More accurate estimation of activation energy (pages 517–522)

      Shogo Sakai, Taro Udagawa, Shohei Kato and Keita Nakada

      Article first published online: 5 MAY 2013 | DOI: 10.1002/poc.3119

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      The estimation of the activation energy of the trimerization of ethyne to form benzene by ab initio molecular orbital and density functional methods depended on the calculation levels. Here, we proposed the more accurate estimation of the activation energy and reaction path with the relation between the activation energy and interaction energy.

  5. Letter to the Editor

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Review
    5. Research Articles
    6. Letter to the Editor

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