Amide interactions in aqueous and organic medium

Spencer, J. N.; Berger, Scott K.; Powell, Carla; Henning, Bruce D.; Furman, Gary S.; Loffredo, William M.; Rydberg, Elaine M.; NEUBERT, R. A.; Shoop, C. E.; Blauch, David N.

doi:10.1021/j150609a028

Cited by 74 publications

(36 citation statements)

References 7 publications

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“…The fact that this process is exothermic has been interpreted as a consequence of hydrogen bond formation between the carbonilic oxygen of the amide and the molecules of water [23], which have been confirmed by Raman spectroscopy [24]. Calculations on the water-water and water-amide interaction energy have shown that hydrogen bonds between water and amides are stronger than between water molecules [25]. Results for the excess enthalpy as a function of the water mole fraction obtained in the present work are compared with experimental data in Figure 1.…”

Section: Energeticmentioning

confidence: 84%

Study of Water and Dimethylformamide Interaction by Computer Simulation

Cordeiro

Freitas

1999

Zeitschrift Für Naturforschung A

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Monte Carlo simulations of water-dimethylformamide (DMF) mixtures were performed in the isothermal and isobaric ensemble at 298.15 K and 1 atm. The intermolecular interaction energy was calculated using the classical 6-12 Lennard-Jones pairwise potential plus a Coulomb term. The TIP4P model was used for simulating water molecules, and a six-site model previously optimised by us was used to represent DMF. The potential energy for the water-DMF interaction was obtained via standard geometric combining rules using the original potential parameters for the pure liquids. The radial distribution functions calculated for water-DMF mixtures show well characterised hydrogen bonds between the oxygen site of DMF and hydrogen of water. A structureless correlation curve was observed for the interaction between the hydrogen site of the carbonyl group and the oxygen site of water. Hydration effects on the stabilisation of the DMF molecule in aqueous solution have been investigated using statistical perturbation theory. The results show that energetic changes involved in the hydration process are not strong enough to stabilise another configuration of DMF than the planar one.

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Section: Energeticmentioning

confidence: 84%

Study of Water and Dimethylformamide Interaction by Computer Simulation

Cordeiro

Freitas

1999

Zeitschrift Für Naturforschung A

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“…The enthalpy of hydrogen bond fomiation, AHHB, may then be calculated from where AH,^ and &isM are the enthalpies of solution of the acid and model compounds; McA and AHcM are the cavity formation terms for the pure base; AHcA and AHcM' are the cavity terms for the reference solvent; AHiA and AHiM are the interaction terms due to dipolarand van der Waals forces for the pure base; and AHiA' and AHiM' are the corresponding terms for the reference solvent. A complete discussion of this method has been previously reported (6,7).…”

Section: Methodsmentioning

confidence: 99%

“…In particular, Somsen and co-workers (3)(4)(5) have studied the thermodynamic enthalpies of aqueous solutions of urea and methyl-substituted ureas. We have made additional calorimetric measurements on these ureas and have applied a previously developed model (6) to provide more detailed information on the first solvation sphere of dilute solutions of urea in DMF and water.…”

Section: Introductionmentioning

confidence: 99%

Solvation of urea and methyl-substituted ureas by water and DMF

Spencer¹,

Hovick²

1988

Can. J. Chem.

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. Can. J. Chem. 66, 562 (1988).The hydrogen bond enthalpies of urea and methyl-substituted ureas with water and DMF have been determined by the pure-base calorimetric method. Transfer enthalpies between water and DMF have been calculated for dilute solutions of the ureas according to a previously developed model. The first solvation sphere of urea in water consists of five water molecules. Solvation spheres are given for other methyl-substituted ureas in water and DMF.

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“…The calorimeters and methods of analysis have been previously described (2,3). Purifications of water and methanol have been reported (I).…”

Section: Methodsmentioning

confidence: 99%

Solvation of aminopyridines by water and methanol

Spencer¹,

Barton²,

Smith³

et al. 1983

Can. J. Chem.

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Can. 3 . Chem. 61, 194 (1983). The hydrogen-bonded interactions by water and methanol in the first solvation shell of 2-aminopyrimidine, 2-, 3-, and 4-aminopyridine were determined by calorimetric analysis. The aminopyridines are enthalpically more stable in methanol than in water. This is due to methanol interactions at the amino nitrogen which do not seem to occur in water. The transfer enthalpies from water to methanol are determined primarily by the making and breaking of hydrogen bonds in the two solvents.

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Amide interactions in aqueous and organic medium

Cited by 74 publications

References 7 publications

Study of Water and Dimethylformamide Interaction by Computer Simulation

Study of Water and Dimethylformamide Interaction by Computer Simulation

Solvation of urea and methyl-substituted ureas by water and DMF

Solvation of aminopyridines by water and methanol

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