Partition coefficients of some conjugated heteroenoid compounds in the system cyclohexane–water

Lough, C. E.; Silver, R. F.; McClusky, F.K.

doi:10.1139/v68-320

Cited by 3 publications

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“…The partition coefficients were determined as in the earlier papers (1,2). Each determination was done at least twice, the phases remaining in contact for 10 and 15 min with periods of shaking of 5 and 10 min respectively.…”

Section: 749 (1951)mentioning

confidence: 99%

Partition coefficients of some N-alkyl- and N,N-dialkyl-derivatives of some cinnamamides and benzalcyanoacetamides in the system cyclohexane–water

Delaney¹,

Currie²,

Holmes³

1969

Can. J. Chem.

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Section: 749 (1951)mentioning

confidence: 99%

Partition coefficients of some N-alkyl- and N,N-dialkyl-derivatives of some cinnamamides and benzalcyanoacetamides in the system cyclohexane–water

Delaney¹,

Currie²,

Holmes³

1969

Can. J. Chem.

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“…This anomaly prompted the examination of the partition coefficients of a series, 1, of trans-cinnamoyl derivatives of some long-chain and large-ring amines, prepared by the method of Papa et al (2), to determine the effect of these hydrophobic groups L I~O I I partition coefficient. Logarithms of the partition coefficients, log K, in cyclohexane-water were determined by methods previously described (1,3,4), and these values are listed in Table 1, along with those calculated from es. 111.…”

mentioning

confidence: 99%

“…[3] M) of the solubility in cyclohexane of 1 compo~lnds (Table 2) where R1 = H and R varies from CH, to n-C,Hl, requires that changes in the partition coefficients with increase in the number of carbon atoms in the substituent chain must be due, primarily, to variation in their solubilities in water. Accordingly, calculations of the water solubilities (Table 2) of the above series of compounds gave values from 1 x l o p 2 to -2 x M. These solubility relationships were just reversed for cinnamamides derived from secondary amines containing two identical alkyl groups.…”

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confidence: 99%

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Partition coefficients and ultraviolet absorption maxima for the cinnamoyl derivatives of some long-chain and large-ring amines

Currie¹,

Holmes²

1970

Can. J. Chem.

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Partition coefficients of the title compounds in the system cyclohexane–water do not increase steadily with increasing chain length or ring size but level off to a limiting value. Reasons are advanced to account for this observation. Absorption maxima, on the other hand, are not influenced by the size of the ring or the length of the chain but are dependent only upon the degree of substitution on the amide nitrogen atom.

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Determination of the thermodynamics of the methyl group in solutions of drug molecules

Davis

1973

Journal of Pharmacy and Pharmacology

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The contribution of the CH, group to the solution thermodynamics of drug molecules is dependent on whether it is attached to a ring system or is in the terminal position in an aliphatic chain. In the former case group contributions for CH, are very similar to those found for the CH2 group. For instance, in partition, the CH, group contribution (log FCH,) is in the range 0.65 to 0.28 (AG = 2.303 RT log FCHJ and is dependent on the polarity of the organic solvent. The contribution for the terminal aliphatic CH, is not equivalent to the mid chain CH, and a CH, correction factor or 1.14 to 1.34 kcal mol-l (4.77 to 5.61 kJ mol-l), has been calculated from alkane solubility data and partition studies. The additivity of group contributions and the correct choice of reference state are also discussed.Davis, Higuchi & Rytting (1972) have previously showed that the methylene group contribution to the thermodynamics of solutions of drug molecules could be obtained from activity coefficients, Henry's law constants and partition coefficient data. The free energy of transfer of the CH, group from water to organic solvent ranged from -850 to -450 cal mol-1 (1 cal mol-l = 4.186 kJ mol-l) depending on the nature of the solvent and differences in group values could be rationalized in terms of solvent polarity. In this paper the methyl group is considered.Many authors have assumed that the CH, and CH, contributions are identical (Hansch & Anderson, 1967;Kakovsky, 1957; Hersh, 1971). So that for an alkanol (CnH2n + ,OH)

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Partition coefficients of some conjugated heteroenoid compounds in the system cyclohexane–water

Abstract: Partition coefficients in cyclohexane-water were determined for 160 conjugated heteroenoid compounds and were used to calculate n constants for several component groupings of molecules.

Cited by 3 publications

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Partition coefficients of some N-alkyl- and N,N-dialkyl-derivatives of some cinnamamides and benzalcyanoacetamides in the system cyclohexane–water

Partition coefficients of some N-alkyl- and N,N-dialkyl-derivatives of some cinnamamides and benzalcyanoacetamides in the system cyclohexane–water

Partition coefficients and ultraviolet absorption maxima for the cinnamoyl derivatives of some long-chain and large-ring amines

Determination of the thermodynamics of the methyl group in solutions of drug molecules

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