Solvation and hydrogen bonding of pyridinium ions

Arnett, Edward M.; Chawla, B.; Bell, Larry G.; Taagepera, M.; Hehre, Warren J.; Taft, Robert W.

doi:10.1021/ja00459a034

Cited by 94 publications

(46 citation statements)

References 8 publications

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“…[2][3][4] and references therein. In gas-phase Py-H 2 O clusters, the lone pair of the N atom acts as the proton acceptor of a relatively strong and nearly linear N…HO hydrogen bond.…”

Section: Introductionmentioning

confidence: 99%

Computational investigation of the photoinduced homolytic dissociation of water in the pyridine–water complex

Liu

Sobolewski

Borrelli

et al. 2013

Phys. Chem. Chem. Phys.

108

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Computational investigation of the photoinduced homolytic dissociation of water in the pyridine-water complex / Xiaojun Liu;Andrzej L. Sobolewski;Raffaele Borrelli;Wolfgang Domcke. -In: PHYSICAL CHEMISTRY CHEMICAL PHYSICS. -ISSN 1463-ISSN -9076. -15(2013, pp. 5957-5966. Original Citation:Computational investigation of the photoinduced homolytic dissociation of water in the pyridine-water complex AbstractThe photochemistry of the hydrogen-bonded pyridine-water complex has been investigated with ab initio computational methods. Vertical excitation energies,

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“…[2][3][4] and references therein. In gas-phase Py-H 2 O clusters, the lone pair of the N atom acts as the proton acceptor of a relatively strong and nearly linear N…HO hydrogen bond.…”

Section: Introductionmentioning

confidence: 99%

Computational investigation of the photoinduced homolytic dissociation of water in the pyridine–water complex

Liu

Sobolewski

Borrelli

et al. 2013

Phys. Chem. Chem. Phys.

108

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“…The acidities of pyridinium ions also show attenuation in aqueous solution with a slope of 3 (ref. 13). The attenuation of the substituent effect for the above cases must be directly connected.with a substituent effect on the solvation of the ions.…”

Section: Changes Of Solvation In Protic Solvents Upon Ionic Charge DImentioning

confidence: 97%

“…The LiH(g) were obtained from gas phase proton transfer measurements (ref. 13). The LH(B0) and H5(B) were evaluated from measured heats of vaporization and solution of the pyridines.…”

Section: -N0pymentioning

confidence: 99%

“…The data for the hydrated pyridiniums were obtained from determinations of the temperature dependence of the hydration equilibria (13) and (4). Unfôrtunately,measurements could not be carried out beyond n=4 since at temperatures + H20 = PyH(H20) (13) CNPyH(H20)1 + H20 = CNPyH(H20) (14) low enough for these equilibria to establish, condensation of liquid water on the walls of the reaction chamber occurred. Evidently the equilibrium partial pressure of dissociating water vapor from PyH+(H90) (for n > 4) is larger than the equilibrium vapor pressure of liquid water.…”

Section: -N0pymentioning

confidence: 99%

“…This EE15 was obtained from STO-3G calculations of the electronic energies E + + + + 4CNPyH OH2 + PyH = 4CNPyH + PyH OH2 (15) of the reactants and products of reaction 15 by Hehre (Arnett, Taft, Hehre ref. 13). The calculated iE predicts the right trend, but is almost twice as large as the experimentally observed &H l Considering that the difference between the two values is only 1 kcal/mole one can hardT expect anything better from the calculation.…”

Section: -N0pymentioning

confidence: 99%

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Information on Ion-Solvent Interactions Obtained From the Study of Isolated Complexes Containing the Ion and a Small Number of Solvent Molecules

Kebarle¹,

Davidson²,

Sunner³

et al. 1979

Ions and Ion Pairs and Their Role in Chemical Reactions

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-The measurement of gas phase ion-molecule equilibria by special mass spectrometric techniques (high pressure mass spec., ICR, Flowing Afterglow) provides for the first time abundant and accurate thermochemical data for organic and inorganic ions of interest. The energies of formation so obtained used in Born cycles lead to energies of solvation of ions from gas phase to a partiular solvent. Ion-solvent molecule equilibria Ion±(SS)n_1 + S IoniSZ)n measured in the gas phase with the above techniques lead to LH°n_i n and tG°n, n These data show that the essential features of the enertes of solvatton ofthe ions in a given liquid solvent S are contained in the energetics of the ion solvent molecule clusters Ion±(S2)n where n can be as low as 4 or 5. The substituent effects on the solvation of pyridinium cations and phenoxide anions in protic solvents are examined. Substituents that stabilize the ions in the gas phase (because of charge delocalization) reduce the hydrogen bonding interactions of the solvent with the ion. This can be directly observed by measuring the G° -l n and LH° 1 n values for water clustering to the substituted ions.

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Protonic Acidities and Basicities in the Gas Phase and in Solution: Substituent and Solvent Effects

Taft¹

1983

Progress in Physical Organic Chemistry

210

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Solvation and hydrogen bonding of pyridinium ions

Cited by 94 publications

References 8 publications

Computational investigation of the photoinduced homolytic dissociation of water in the pyridine–water complex

Computational investigation of the photoinduced homolytic dissociation of water in the pyridine–water complex

Information on Ion-Solvent Interactions Obtained From the Study of Isolated Complexes Containing the Ion and a Small Number of Solvent Molecules

Protonic Acidities and Basicities in the Gas Phase and in Solution: Substituent and Solvent Effects

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