Hydrogen Bonds Involving the C-H Link. X.<sup>1</sup> The Solubility of Donor Solutes in Halogenated Hydrocarbons

Marvel, C. S.; Dietz, Frederick C.; Copley, M.

doi:10.1021/ja01866a006

Cited by 24 publications

(6 citation statements)

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“…Marvel et al [28] measured the solubility of benzoin in chloroform and tetrachloromethane and there is an experimental practical water-to-1-octanol partition coefficient of log P ¼ 2.13 [29], giving us a set of 58 equations. The experimental aqueous molar solubility of benzoin of log C sat W ¼ À3:67 can also be included in the regression analysis.…”

Section: Resultsmentioning

confidence: 99%

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Stephens

Loera

Calderas

et al. 2012

Physics and Chemistry of Liquids

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Experimental solubilities are reported for benzoin dissolved in 1 chloroalkane, 15 alcohols, 5 aromatic hydrocarbons, 5 alkyl acetates, 5 alkoxyalcohols and 3 ethers at 298.15 K. The measured solubility data were mathematically correlated with the Abraham solvation parameter model. The solute descriptors that were calculated for benzoin describe the experimental molar solubility data to within an overall average standard deviation of 0.097 log units.

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Section: Resultsmentioning

confidence: 99%

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Stephens

Loera

Calderas

et al. 2012

Physics and Chemistry of Liquids

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“…This conclusion is consistent with the weakness of TCE as a proton donor. [4][5][6] The fact that the carbonyls and ethers show a Te maximum in the CFM mixtures near 60 mol % CFM suggests that the formation of a 2:1 CFM:base bicomplex is the predominant mode of association in these mixtures. The formation of such a bicomplex between CFM and acetone, in which two CFM molecules are most likely directly bonded to each acetone oxygen, has been reported by several authors.12-24-27 Since an ether is in general a stronger base than a carbonyl,20 bicomplex formation of this type Can be expected in ether mixtures as well.…”

Section: Trends In Tabulated22mentioning

confidence: 99%

“…The protons of such hydrocarbons have been shown to be activated to hydrogen bond formation by the attached chlorine atoms. 4,5 Formation of hydrogen-bonded association complexes between chloroform (CFM) and various organic bases has been demonstrated by calorimetry and various spectroscopic techniques.6 Since trichlorethylene (TCE) and dichloromethane (DCM) have also been shown to be capable of serving as electron acceptors in the formation of a hydrogen bond, such complex formation can be expected to occur with these materials as well. In order to examine the effect of this complex formation on the glass transition, the glass transition temperature Tg was measured as a function of composition for binary mixtures of CFM, TCE, and DCM with various electron donors.…”

Section: Introductionmentioning

confidence: 99%

Effect of association complexes on the glass transition in organic halide mixtures

Lesikar¹

1976

J. Phys. Chem.

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Publication costs assisted by St. Cloud State UniversityThe glass transition temperatures of binary mixtures of chloroform, dichloromethane, and trichloroethylene with several Lewis bases have been measured as a function of composition. The glass transition temperatures of the mixtures are shown to be increased by complex formation between the chloride and the base, and the glass transition temperature is shown to increase with base strength. The chloroform mixtures show the greatest effect of complex formation. A cusp is found in the composition dependence of the glass transition temperature T , of mixtures of chloroform with triethylamine. The cusp is found at the equimolar composition. It is taken as evidence for the complete association of chloroform with triethylamine into a 1:l complex at T,. The trichloroethylene mixtures show greater effects of complex formation than do the dichloromethane mixtures, although evidence from the literature seems to indicate that dichloromethane is the stronger acid.

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“…It is regrettable that the results of benzoin solubility in normal solvents are very limited in previous works. Up to now, the solubility of benzoin in supercritical carbon dioxide, − some halogenated hydrocarbons, and dry octan-1-ol are reported. In addition, Stephens and Yang have determined the solubilities of benzoin in some organic monosolvents and solvent mixtures.…”

Section: Introductionmentioning

confidence: 99%

Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K

et al. 2018

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In the present work, the benzoin solubility in ethanol, methanol, n-propanol, isopropyl alcohol, n-butanol, acetone, ethyl acetate, acetonitrile, cyclohexane, butyl acetate, isobutyl alcohol, and toluene and ethyl acetate + ethanol solvent mixtures was measured by using the static method at the temperature range from 273.15 to 313.15 K under atmospheric pressure (101.1 kPa). The solubilities in mole fraction increased with increasing temperature and followed the order from high to low in the selected monosolvents: ethyl acetate > acetone > butyl acetate > (acetonitrile, toluene) > methanol > ethanol > n-propanol > n-butanol > isobutyl alcohol > isopropyl alcohol > cyclohexane; and for the ethyl acetate + ethanol mixture, the mole fraction solubilities of benzoin increased with the increase in temperature and ethyl acetate mass fraction. The obtained solubility of benzoin in neat solvents was correlated with the Apelblat equation, λh equation, and Wilson and NRTL models; and in solvent mixtures of ethyl acetate (w) + ethanol (1 – w), with the Jouyban–Acree, van’t Hoff–Jouyban–Acree and Apelblat–Jouyban–Acree models. The largest value of root-mean-square deviation was 4.02 × 10–4, and relative average deviation was 2.36 × 10–2. Furthermore, the mixing enthalpy, mixing Gibbs energy, mixing entropy, activity coefficients under infinitesimal concentration (γ1 ∞), and reduced excess enthalpy (H 1 E,∞) were deduced.

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Hydrogen Bonds Involving the C-H Link. X.¹ The Solubility of Donor Solutes in Halogenated Hydrocarbons

Cited by 24 publications

References 0 publications

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Effect of association complexes on the glass transition in organic halide mixtures

Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K

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Hydrogen Bonds Involving the C-H Link. X.1 The Solubility of Donor Solutes in Halogenated Hydrocarbons

Cited by 24 publications

References 0 publications

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Determination of Abraham model solute descriptors for benzoin based on measured solubility ratios

Effect of association complexes on the glass transition in organic halide mixtures

Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K

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Hydrogen Bonds Involving the C-H Link. X.¹ The Solubility of Donor Solutes in Halogenated Hydrocarbons