Hydrogen bonding. Part 7. A scale of solute hydrogen-bond acidity based on log K values for complexation in tetrachloromethane

Abraham, Michael H.; Grellier, Priscilla L.; Prior, David V.; Duce, Philip P.; Morris, Jeffrey J.; Taylor, Peter J.

doi:10.1039/p29890000699

Cited by 401 publications

(449 citation statements)

References 13 publications

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“…for acidity and p? for basicity, which were defined to be lhearly related to the equilibrium constants for forming 1:l complexes between the solute molecule and a given reference hydrogen bond donor or acceptor, in CC14 (37)(38)(39). In this study, we have focused on a?…”

Section: Resultsmentioning

confidence: 99%

Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O–H infrared frequency shifts

Hagelin¹,

Murray²,

Politzer³

et al. 1995

Can. J. Chem.

165

140

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Family-independent relationships between computed molecular surface properties and solute hydrogen bond aciditylbasicity and solute-induced methanol 0-H infrared frequency shifts are presented. The molecular surface quantities, computed at the ab initio HFl6-31G* level, are primarily related to the electrostatic potential of the molecule, but also include the average local ionization energy on its surface.

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Section: Resultsmentioning

confidence: 99%

Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O–H infrared frequency shifts

Hagelin¹,

Murray²,

Politzer³

et al. 1995

Can. J. Chem.

165

140

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“…Since HBDs of biological interest are mostly confined to OH and NH groups and since HBAs vary much more in character, we have first covered the scale of HBA strength. For HBD strength scale, we presently refer the reader to the log K A H [78] or log K α scales [25]. The validity range of the pK HB scale, constructed towards a phenol in a medium of low reaction field, extends over many OH and NH donors and to higher reaction fields than the definition one.…”

Section: American Journal Of Modeling and Optimizationmentioning

confidence: 99%

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Yunta¹

2017

AJMO

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The effect of weak intermolecular interactions on the binding affinity between ligand-protein complexes plays an important role in stabilizing a ligand at the interface of a protein structure. In this review article, we will explore the different ways of taking into account these interactions, mainly intramolecular hydrogen bonds, in docking calculations. Their possible limitations and their suitable application domains are highlighted. Inspection of the outliers of this study probed very stimulating, as it provides opportunities and inspiration to medicinal chemists, being a reminder of the impact that minimal chemical modifications can have on biological activities.

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“…Here, the last approach was used to estimate ∑α H 2 for several CFCs and HCFs. In a previous study, Abraham and coworkers [6] highlighted a relationship between the 1:1 hydrogen bond acidity, α H 2 and the Hammet inductive parameter, σ Ι for a few halogenated compounds. We use the same approach to establish a correlation between ∑α H 2 and σ Ι for a few CFCs and HFCs.…”

Section: Estimation Of ∑α H 2 Valuesmentioning

confidence: 99%

“…In solvation situation, ∑α H 2 the 'effective' or 'summation' solute hydrogen bonding acidity must be considered [6]. Here, the solute is surrounded by solvent molecules and undergoes multiple hydrogen bonding.…”

Section: Estimation Of ∑α H 2 Valuesmentioning

confidence: 99%

“…The dependent variable, log SP, is some property of a series of solutes in a fixed phase, and the independent variables, or descriptors, are solute properties as follows: R 2 is an excess molar refraction [4], π 2 H is the solute dipolarity/polarizability [5], ∑α H 2 and ∑β 2 H are, respectively, the solute overall hydrogen bond acidity and basicity [6]. Vx is the MacGowan characteristic volume in units of (dm 3 mol -1 /100) [7] and logL 16 is a descriptor, where L 16 is the solute gas-hexadecane partition coefficient at 298 K [8].…”

Section: Introductionmentioning

confidence: 99%

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Solvation properties of refrigerants, and the estimation of their water–solvent and gas–solvent partitions

Abraham

Gola

Cometto‐Muñiz

et al. 2001

Fluid Phase Equilibria

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We have previously used two general solvation equations to correlate and to interpret a wide variety of physicochemical and biochemical properties of compounds (solutes). Application of these equations requires a knowledge of the relevant solute descriptors, viz. R 2 , the excess molar refraction, π 2 H , the solute dipolarity/polarizability, ∑α H 2 , ∑β 2 H , the solute overall hydrogen bond acidity and basicity, and logL 16 , where L 16 is the solute gas-hexadecane partition coefficient at 298 K. We have also shown that these solute descriptors can be obtained from partition coefficients of solutes in various water-solvent and gas-solvent systems. Here, we use this approach to calculate solute descriptors for a series of 18 organofluorocarbons, classed as refrigerants, including chlorofluorocarbons, hydrochlorofluorocarbons, hydrofluorocarbons and perfluorocarbons, using Henry's law coefficients in water and five organic solvents that we have already measured. These data have been used to calculate Ostwald solubility coefficients, log L. Gas-water and gas-solvent partitions have been then combined to give log P for partition between water and solvent. A number of log P and L values have also been taken from the Medchem97 database. There are enough data to obtain the above descriptors for the 18 organofluorocarbons, and then to estimate log P and L values in a large number of other solvents. The chemosensory properties of the organofluorocarbons are also estimated.

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Hydrogen bonding. Part 7. A scale of solute hydrogen-bond acidity based on log K values for complexation in tetrachloromethane

Abstract: SK 70 4TG * These K z values are formally equivalent to equilibrium constants for the series of acids against a particular base with L, = 1 and D, = 0.

Cited by 401 publications

References 13 publications

Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O–H infrared frequency shifts

Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O–H infrared frequency shifts

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Solvation properties of refrigerants, and the estimation of their water–solvent and gas–solvent partitions

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