Journal of Physical Organic Chemistry

Cover image for Journal of Physical Organic Chemistry

December 2009

Volume 22, Issue 12

Pages 1127–1238

  1. Award Reviews

    1. Top of page
    2. Award Reviews
    3. Review Commentaries
    4. Research Articles
    5. Short Communications
    1. Dispersion interactions in density-functional theory (pages 1127–1135)

      Erin R. Johnson, Iain D. Mackie and Gino A. DiLabio

      Version of Record online: 9 SEP 2009 | DOI: 10.1002/poc.1606

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      Computational methods that allow for the modeling of dispersion, and other weak non-covalent, interactions within density-functional theory are reviewed.

  2. Review Commentaries

    1. Top of page
    2. Award Reviews
    3. Review Commentaries
    4. Research Articles
    5. Short Communications
    1. Electrochemistry in tetrahydrofuran and at low temperature: protocol, procedures and methods (pages 1136–1141)

      Ronan Baron, Neil M. Kershaw, Timothy J. Donohoe and Richard G. Compton

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/poc.1574

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      This paper reflects both the interest of electrochemical studies in THF and at low temperature and our efforts to improve the experimental methodology.

  3. Research Articles

    1. Top of page
    2. Award Reviews
    3. Review Commentaries
    4. Research Articles
    5. Short Communications
    1. Gibbs energy of cooperative hydrogen-bonding interactions in aqueous solutions of amines and pyridines (pages 1142–1147)

      Boris N. Solomonov, Igor A. Sedov and Aydar A. Akhmadiyarov

      Version of Record online: 1 JUN 2009 | DOI: 10.1002/poc.1566

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      The Gibbs energies of hydrogen bonding with water are determined using a novel method for a number of aliphatic amines and pyridines in their aqueous solutions. Their hydrogen bonds with water associates are found to be strengthened in comparison with 1:1 complexes due to cooperative effects.

    2. Reactivity of mixed organozinc and mixed organocopper reagents. Part 4: a kinetic study of group transfer selectivity in C[BOND]C coupling of mixed diorganocuprates (pages 1148–1154)

      Ender Erdik and Duygu Özkan

      Version of Record online: 29 JUL 2009 | DOI: 10.1002/poc.1567

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      The competitive rate data and Taft relationships for the coupling of bromomagnesium n-butyl (substituted phenyl) cuprates with alkyl bromides show that selective n-butyl transfer can be explained by oxidative addition mechanism. Taft reaction constants also show that the residual group, FG-C6H4 in the mixed cuprate, n-Bu(FG-C6H4)CuMgBr changes the ability of the copper nucleophile to react with electrophile, RBr.

    3. Effect of ortho substituents on carbonyl carbon 13C NMR chemical shifts in substituted phenyl benzoates (pages 1155–1165)

      Vilve Nummert, Mare Piirsalu, Vahur Mäemets, Signe Vahur and Ilmar A. Koppel

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/poc.1569

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      The influence of the inductive, resonance and steric factors on the carbonyl carbon 13C NMR chemical shift, δCO, in ortho-, meta- and para-substituted phenyl benzoates and R-substituted alkyl benzoates

    4. Structural and vibrational study of 2-(2′- furyl)-4,5-1H-dihydroimidazole (pages 1166–1177)

      Juan Zinczuk, Ana Estela Ledesma, Silvia Antonia Brandán, Oscar Enrique Piro, Juan Jesús López-González and Aída Ben Altabef

      Version of Record online: 1 JUL 2009 | DOI: 10.1002/poc.1572

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      In this study, 2-(2′-furyl)-4,5-1H-dihydroimidazole was prepared and characterized using infrared, Raman, and multidimensional nuclear magnetic resonance spectroscopies. The two conformations of this species obtained by rotating 180°, approximately, around the C[BOND]C inter-ring bond were detected in gas phase, and only one of them was present in the solid phase.

    5. Intra- and intermolecular N[BOND]H···O hydrogen bonds in pyrrolyl derivatives of indane-1,3-dione – experimental and theoretical study (pages 1178–1187)

      M. Sigalov, B. Shainyan, N. Chipanina, I. Ushakov and A. Shulunova

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/poc.1573

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      Spectroscopic study and theoretical calculations of the pyrrolyl derivatives of 1,3-indandione (X=O, C(CN)2) show the presence of strong intermolecular H-bond in low polar solvent and the equilibrium between two conformers with and without intermolecular H-bond in polar solvents.

    6. Synthesis and rational design of anti-inflammatory compounds: N-phenyl-cyclohexenyl sulfonamide derivatives (pages 1188–1192)

      Gustavo R. Lloret, Álvaro Cunha Neto, Roberto Rittner, Michelle Bitencourt, Matheus P. Freitas and Nilton S. Aquino

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/poc.1575

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      The synthesis of (±)-ethyl 6-[N-(3-nitrophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate, an analog of TAK-242, was achieved. A MIA-QSAR model, which is based on a series of TAK-242 derivatives, was then built and a highly predictive model was produced.

    7. ρ(T, p) model for ionic liquids based on quantitative structure–property relationship calculations (pages 1193–1197)

      Juan A. Lazzús

      Version of Record online: 1 JUL 2009 | DOI: 10.1002/poc.1576

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      Densities of ionic liquids have been estimated using a quantitative structure-property relationship (QSPR) method that involved 11 molecular descriptors. Density data of 238 experimental data sets for 163 ionic liquids were used to obtain the QSPR model for a wide range of temperatures and pressures: 258–393 K and 0.09–207 MPa. Results show that the model to estimate the liquid density (R2 = 0.9307; AARD = 2.00) is accurate enough and gives lower deviations than any other similar QSPR model currently available in the literature.

    8. Theoretical calculations of the kinetics and mechanisms of the gas phase elimination of primary, secondary, and tertiary 2-hydroxyalkylbenzenes (pages 1198–1207)

      Jose R. Mora, Jesus Lezama, José M. Albornoz, Antonio Hernandez, Tania Córdova and Gabriel Chuchani

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/poc.1577

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      The theoretical study of the elimination kinetics of 2-phenylethanol, 1-phenyl-2-propanol and 2-methyl-1-phenyl-2-propanol in the gas-phase has been carried out at the ab initio and DFT levels of theory. The three substrates undergo two parallel elimination reactions. The MP2/6-31G(d,p), MPW1PW91/6-31++G(d,p), and PBEPBE/6-31G(d,p) were found in good agreement with the experimentals.

    9. Effects of alkyl chain lengths of gallates upon their distribution and reactivity towards diphenylpicryl hydracil radicals in Triton X-100 micellar solutions (pages 1208–1211)

      A. M. Campos, E. Ponce and E. A. Lissi

      Version of Record online: 21 JUL 2009 | DOI: 10.1002/poc.1580

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      The rate of reaction of alkyl gallates with diphenyl picryl hydracil radicals depends on the alkyl chain length. This dependence is due to differences in the gallate partitioning.

    10. Computational studies of the cone and 1,2,3 alternate calix[6]arene bis-crown-4 isomers: structures, NMR shifts, atomic charges, and steric compression (pages 1212–1224)

      Meghan N. Lawson, Michael T. Blanda, Sara J. Staggs, Lauren N. Sederholm and David C. Easter

      Version of Record online: 30 OCT 2009 | DOI: 10.1002/poc.1621

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      The cone and 1,2,3 alternate isomers of calix[6]arene bis-crown 4 were investigated computationally. Good agreement between calculated values and experimental results was obtained from HF/6-31g(d) NMR calculations based on B3LYP/6-31g(d) structure optimizations that imposed no molecular symmetry constraints. Analysis reveals that atomic charges, electrostatic forces, and local dipoles–but not bond lengths–are strongly correlated to spectroscopic manifestations of steric compression.

    11. Electron reorganization in allowed and forbidden pericyclic reactions: multicenter bond indices as a measure of aromaticity and/or anti-aromaticity in transition states of pericyclic electrocyclizations (pages 1225–1232)

      Marcos Mandado and Robert Ponec

      Version of Record online: 27 JUL 2009 | DOI: 10.1002/poc.1589

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      Differences in the electron reorganization in the course of allowed and forbidden pericyclic reactions can be unequivocally represented by the monitoring of the variation of the multicenter bond indices along the corresponding reaction paths. Ab-initio results confirm the predictions of the topological models.

  4. Short Communications

    1. Top of page
    2. Award Reviews
    3. Review Commentaries
    4. Research Articles
    5. Short Communications
    1. Mechanistic studies of oxidation reactions by fluorescence spectroscopy: a critical assessment (pages 1233–1238)

      Alexander Schmitt, Babette Hinkeldey, Benjamin Hötzer and Gregor Jung

      Version of Record online: 21 AUG 2009 | DOI: 10.1002/poc.1604

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      The attack of reactive species at a double bond is detected by a change of fluorescence color due to the shortening of the chromophoric system. The substrate, a styryl-BODIPY-dye, is converted by dihydroxylation agents to several strongly fluorescent products of unknown structure.

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