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Journal of Physical Organic Chemistry

Cover image for Vol. 27 Issue 1

January 2014

Volume 27, Issue 1

Pages i–iii, 1–73

  1. Issue Information

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

      Article first published online: 16 DEC 2013 | DOI: 10.1002/poc.3203

  2. Early Excellence Profiles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Research Articles
    1. You have free access to this content
  3. Research Articles

    1. Top of page
    2. Issue Information
    3. Early Excellence Profiles
    4. Research Articles
    1. You have free access to this content
      1,3-Bis(2′-hydroxyethyl)imidazolium ionic liquids: correlating structure and properties with anion hydrogen bonding ability (pages 2–9)

      Feng Deng, Zachary K. Reeder and Kevin M. Miller

      Article first published online: 5 SEP 2013 | DOI: 10.1002/poc.3198

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      A series of 1,3-bis(2′-hydroxyethyl)imidazolium ionic liquids were synthesized and analyzed by 1H NMR spectroscopy and thermogravimetric analysis. Correlations of chemical shift values and thermal stability (Td) values with anion hydrogen bonding capabilities are discussed. Density functional theory calculations indicated a preference for the anion to be located above the imidazolium ring and in close proximity to both hydroxyl groups.

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      Comparative theoretical studies of high energetic cyclic nitramines (pages 10–17)

      Guozheng Zhao and Ming Lu

      Article first published online: 3 SEP 2013 | DOI: 10.1002/poc.3199

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      A systematic study on the energetic properties of designed cyclic nitramines was reported. Results indicate that all cyclic nitramines have better detonation properties than 1,3,5-trinitro-1,3,5-triazacyclohexane and 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and provide theoretical support for molecular design of high energy density materials and experimental synthesis.

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      Study of scavenging action of zingerone towards the OH radical: formation of vanillin and ferulic acid (pages 18–26)

      Ajit Kumar Prasad and P. C. Mishra

      Article first published online: 11 SEP 2013 | DOI: 10.1002/poc.3200

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      The scavenging action of zingerone, a phenolic antioxidant, towards the hydroxyl radical has been studied employing the density functional theory. It has been shown how following certain steps of hydrogen abstraction and addition reactions and using a few OH radicals along with zingerone or its degradation products, two other antioxidants, namely vanillin and ferulic acid, can be formed.

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      Hydration of nitriles: an examination in terms of No Barrier Theory (pages 27–37)

      J. Peter Guthrie, Jacky C.-H. Yim and Qiang Wang

      Article first published online: 4 NOV 2013 | DOI: 10.1002/poc.3226

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      Nitrile hydrolysis is surprisingly slow despite the favorable thermodynamics of hydrolysis. In terms of Marcus Theory, the intrinsic barriers for acid and base-catalyzed hydration are higher for nitriles than for amides. No Barrier Theory provides both a qualitative explanation of this slow reaction and a method for quantitative prediction of rates. Although agreement with experiment was achieved with pKa values estimated using such experimental data as there are, and physical organic reasoning, agreement was improved by adjusting the pKa values.

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      A new method for functionalizing α,γ-dinitro compounds at the β-position: application to the cyclization of β-alkoxy-α,γ-dinitro compounds (pages 38–46)

      Peter A. Wade, Christopher E. Castillo and Nicholas Paparoidamis

      Article first published online: 23 SEP 2013 | DOI: 10.1002/poc.3227

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      Ethers were obtained from the reaction of 2,4-dibromo-2,4-dinitro-pentane, NaOR, and Br2. Selective removal of either one or two Br atoms from the products is described. Cyclization of 2,4-dinitro-3-methoxy-pentane gave a 4,5-dihydroisoxazole-2-oxide and not a cyclopropane.

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      UV filter 2-ethylhexyl 4-methoxycinnamate: a structure, energetic and UV–vis spectral analysis based on density functional theory (pages 47–56)

      Margarida S. Miranda, Luís Pinto da Silva and Joaquim C. G. Esteves da Silva

      Article first published online: 1 OCT 2013 | DOI: 10.1002/poc.3235

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      2-Ethylhexyl 4-methoxycinnamate (EHMC) is a very commonly used UVB filter that is known to isomerize from the (E) to the (Z) isomer in the presence of light.

      High level quantum chemical calculations using density functional theory have been used to study the gas-phase molecular structure of EHMC and its energetic stability in both the gas and aqueous phases. Long-range corrected DFT calculations in implicit water were made to understand the excited state properties of the (E) and (Z) isomers of EHMC.

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      Phosphorylated amino derivatives of thiacalix[4]arene as membrane carriers: synthesis and host–guest molecular recognition of amino, hydroxy and dicarboxylic acids (pages 57–65)

      Olga A. Mostovaya, Maria N. Agafonova, Andrey V. Galukhin, Bulat I. Khayrutdinov, Daut Islamov, Olga N. Kataeva, Igor S. Antipin, Alexander I. Konovalov and Ivan I. Stoikov

      Article first published online: 16 OCT 2013 | DOI: 10.1002/poc.3236

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      Promising membrane transport and separation systems for selected dicarboxylic, α-hydroxy- and α-amino acids based on thiacalixarene platform have been developed. As was established by UV–vis spectroscopy, membrane extraction and HPLC, the substitution of amino groups by aminophosphonate units significantly enhances the selectivity of host molecules that bind to aspartic and glycolic acids.

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      2-Methoxynaphthylnaphthoquinone and its solvate: synthesis and structure–properties relationship (pages 66–73)

      Oleg M. Demchuk, I. Justyniak, B. Miroslaw and R. Jasinski

      Article first published online: 6 NOV 2013 | DOI: 10.1002/poc.3237

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      Because of their unique visual optic and electronic properties, substituted quinones are commonly used as dyes and pigments; nevertheless, a theoretic background of relationship between the structures and optical properties of such compounds seems to be still undeveloped. Proposed herein is an interpretation of intriguing optical properties of two crystalline forms of 2-methoxynaphth-1-yl-naphthoquinone, based on detailed spectral and structural characterization, as well as, DFT and MP2 computations that clearly connects the conformation of the molecules with their UV–VIS spectra and electronic properties.

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