Journal of Physical Organic Chemistry

Cover image for Vol. 26 Issue 11

November 2013

Volume 26, Issue 11

Pages i–iii, 869–952

  1. Issue Information

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Research Articles
    1. Issue Information (pages i–iii)

      Version of Record online: 23 OCT 2013 | DOI: 10.1002/poc.3043

  2. Early Excellence Profiles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Research Articles
  3. Research Articles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Research Articles
    1. Comparative study of p-amino benzhydrazide and m-amino benzhydrazide by free radicals and free electron transfer (pages 870–878)

      Pradnya Nalawade, Sergej Naumov and Sudhir Kapoor

      Version of Record online: 14 AUG 2013 | DOI: 10.1002/poc.3182

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      The reactions of OH radical with p-amino benzhydrazide (PABH) and m-amino benzhydrazide were studied by pulse radiolysis technique and density functional theory calculations. Relative energies E0 and Gibbs free energies ΔG (kcal mol-1, given in parentheses) were calculated for the most probable reaction pathways.

    2. Predicting DNA–intercalator binding: the development of an arene–arene stacking parameter from SAPT analysis of benzene-substituted benzene complexes (pages 879–884)

      Laura K. E. Hardebeck, Charles A. Johnson, Graham A. Hudson, Yi Ren, Michelle Watt, Charles C. Kirkpatrick, Brent M. Znosko and Michael Lewis

      Version of Record online: 27 AUG 2013 | DOI: 10.1002/poc.3184

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      A novel arene–arene stacking parameter, designated Ππ, has been developed from symmetry-adapted perturbation theory energy decomposition studies of benzene-substituted benzene dimers. Substituted naphthalimides were synthesized, and the binding to DNA was measured via optical melting studies. The Ππ substituent constant was utilized in a QSAR study to predict the DNA binding of the substituted naphthalimide intercalators.

    3. Stereoelectronic effects in Menshutkin-type SN2 reactions: theoretical study based on through-space/bond orbital interaction analysis (pages 885–891)

      Lizhi Jiang, Yuuichi Orimoto and Yuriko Aoki

      Version of Record online: 5 AUG 2013 | DOI: 10.1002/poc.3186

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      Through-space/bond orbital interaction analysis was applied to investigate the stereoelectronic effect on stabilizing the transition state of SN2 reactions. Substituents (–C6H5 and –CHO groups) lower the activation energies by strengthening the orbital interactions of transition states. The activation energy increases close to the value of the system, which is without such substituents, when the orbital interactions are deleted.

    4. The quest for a better system for evaluating pi-electron substituent constant: a comparison of benzoic, acrylic and tria-, penta-, heptafulvene-based carboxylic acids. A computational study (pages 892–897)

      Wojciech P. Oziminski

      Version of Record online: 12 AUG 2013 | DOI: 10.1002/poc.3187

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      Gibbs free energies of dissociation calculated at the B3LYP/6-311++G(d,p) level of theory for 13 substituents show that acrylic acid is 1.59 times more sensitive to substituent effect than para-benzoic acid and thus, is a good candidate for evaluation a pi-electron substituent constant.

    5. Structure and detonation performance of a novel HMX/LLM-105 cocrystal explosive (pages 898–907)

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

      Version of Record online: 12 AUG 2013 | DOI: 10.1002/poc.3188

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      Previous studies have shown that cocrystal explosive is one of the most promising approaches to decrease sensitivity of high energy materials and maintain their detonation performance. In this work, a novel cocrystal composed of HMX and LLM-105 was designed and theoretically investigated. Calculation shows that HMX/LM-105 cocrystal possesses strong intermolecular interactions, insensitivity, thermal stability, and good detonation performance.

    6. 2,2,9,9-Tetramethylcyclonona-3,5,7-trienylidene vs. its heterocyclic analogues: A quest for stable carbenes at DFT (pages 908–916)

      Mohammad Zaman Kassaee, Maryam Koohi, Reza Mohammadi and Monireh Ghavami

      Version of Record online: 23 AUG 2013 | DOI: 10.1002/poc.3189

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      Cyclonona-3,5,7-trienylidene (X = CH2), and its derivatives with: (a) π-donor/σ-attractors, X = NH, NMe, Ntbutyl, NPh, O; (b) π-donor/σ-donors, X = PH, S; and (c) π-attractor/σ-donor, X = BH, AlH, SiH2. The order of stability based on singlet–triplet energy gap (ΔEs–t / kcalmol−1) is: ΔEs–t: X = CMe2 > NH > NMe > O > NtButyl ≥ NPh ≥ BH > S > PH > CH2 > SiH2.

    7. Network of secondary-substituted adamantane amines (pages 917–926)

      Anirban Panda, Subramaniam Vijayakumar, Douglas J. Klein and Anton Ryzhov

      Version of Record online: 5 SEP 2013 | DOI: 10.1002/poc.3190

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      A set of 42 diastereomeric structures resulting from the secondary-substituted adamantane skeleton are placed into a substitution-reaction partial ordering. A systematic group-function-like cluster expansion of these total energies and associated internal energies are reported to support the idea of partial ordering as worthwhile.

    8. A comparative study of radical cations of thiourea, thiosemicarbazide, and diethylthiourea in aqueous sulphuric acid media employing pulse radiolysis technique (pages 927–932)

      Ghasiram Dey

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/poc.3191

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      Radical cations of thioureas in high acidic H2SO4 solvents. The acid-base conjugate forms of thiourea transients were observed (pka1 = -0.32 and pKa2 = -4.33). Significant variation in decay half-life of thiosemicarbazide radical cations as compared with radical cations of thiourea and diethylthiourea.

    9. Theoretical studies on the reductive elimination reaction mechanism from neutral palladium(IV) sulfinate complexes (pages 933–938)

      Hujun Xie, Furong Lin, Qunfang Lei and Wenjun Fang

      Version of Record online: 27 AUG 2013 | DOI: 10.1002/poc.3192

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      Detailed reaction mechanisms of reductive elimination from neutral palladium(IV) sulfinate complexes have been investigated with the aid of density functional theory calculations. The calculation results reveal that the neutral palladium(IV) sulfinate complexes have four possible reductive elimination pathways, via the C—S, C—C, C—Cl, and desulfitative C—C bond formation to give different products, and the formation of the C—S bond-containing product is kinetically more favorable over the formation of other products.

    10. Theoretical study of energetic trinitromethyl-substituted tetrazole and tetrazine derivatives (pages 939–947)

      Zhichao Liu, Qiong Wu, Weihua Zhu and Heming Xiao

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/poc.3197

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      Tetrazine and tetrazole derivatives with trinitromethyl substituents were theoretically studied. Most of them are qualified by excellent detonation performance and acceptable stability.

    11. On the use of β-carotene as a probe for solvent polarizability (pages 948–952)

      Javier Catalán

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/poc.3201

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      According to McRae (J. Phys. Chem., 1957, 61, 562), if the target electronic transition is only sensitive to dispersion interactions in both nonpolar and polar solvents, the shape of the absorption band and its vibronic structure should be preserved in any type of medium.

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