The n-octanol and n-hexane/water partition coefficient of environmentally relevant chemicals predicted from the mobile order and disorder (MOD) thermodynamics

Ruelle, Paul

doi:10.1016/s0045-6535(99)00268-4

Cited by 93 publications

(91 citation statements)

References 117 publications

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“…Experimental determination of S for hydrophobic compounds are very inaccurate -in these cases water solubility estimated by mobile order thermodynamics presented by Ruelle and his coworkers [15][16][17] are more reliable. Unfortunately, all their results are only for one temperature (25 O C).…”

Section: Solubility In Water: Watsolumentioning

confidence: 99%

“…Unfortunately, all their results are only for one temperature (25 O C). WATSOLU program is our modification of Ruelle's equations [16,17] to consist of separate temperature non-dependent and dependent parts for calculation of As and Bs coefficients to use in eqn (5) and first applied to the As and Bs evaluation for selected POPs [8] and synthetic musks [10] …”

Section: Solubility In Water: Watsolumentioning

confidence: 99%

“…TMK = melting point (K). DB = solubility parameter of Ruelle [16]. MAXW = the greatest value of KAccW(i) or KDonW(i) in water.…”

Section: Solubility In Water: Watsolumentioning

confidence: 99%

“…Ruelle applied the mobile order thermodynamics for Log Kow at 25 O C [16]. The procedure was to subtract solubility equations for Log S in water-saturated n-octanol and in pure water from each other, which resulted to equation of Log Kow.…”

Section: Octanol-water Partition Coefficient: Tdklow Programmentioning

confidence: 99%

“…Here 124.2 is the reduced molar volume of water-saturated n-octanol, rw is structuration factor of water = 2.0, ro is structuration factor for water-saturated n-octanol (= 1.275). KaccO(i) and KdonO(i) are stability constants of proton acceptor and donor groups in octanol, and MAXO the greatest value of KoO(i) and KohO(i) for solute in n-octanol [16].…”

Section: ) -σN Oh (J)*(boh + Rw -Ro))/ln10 (13) ∆Acc = σVacc(i)*(logmentioning

confidence: 99%

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Estimation of vapour pressure, solubility in water, Henry’s law function, and Log Kow as a function of temperature for prediction of the environmental fate of chemicals

Paasiv́irta¹

2006

WIT Transactions on Biomedicine and Health, Vol 10

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Environmental risk R estimation of a chemical is based on predicting exposure of biota (PEC) in media and harmful effect potency as PNEC from (eco) toxicology. For default emission Eo, numerical relative risk is expressed as Ro = PEC/PNEC. Using the risk limit Ro ≥1, the risk emission is RE = Eo/Ro. PEC can be estimated by the fate modeling. Our FATEMOD model computes the fate of chemicals in an environment defined as a catchment area. In this model, the substance properties (liquid state) of vapour pressure Pl, water solubility S, Henry's law coefficient H (Pl/S), lipophility Kow, and the reaction half-life times are automatically computed as a function of temperature. This feature is unique, thus far, in fate models. The physical properties in the environmental temperature range are obtained from the equation: Log Prop(i) = Ai -Bi /T (T in degrees Kelvin). We have learnt to determine the coefficients Apl,Bpl (for Pl), As,Bs (for S), Ah,Bh (for H) and Aow,Bow (for Kow) from thermodynamic equations of these properties as functions of molecular parameters and temperature T by dividing the equation into two parts: 1) T absent and 2) T present. The results compare well with expensive direct measurement results and also with results from retention time comparisons by temperature-controlled GC (for Pl) and HPLC (for S). In reasonable risk predictions for variable climates such as in Nordic countries, the ambient temperature cannot be ignored. Examples of temperature-adjusting FATEMOD runs in chemical risk estimations are given.

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Section: Solubility In Water: Watsolumentioning

confidence: 99%

Section: Solubility In Water: Watsolumentioning

confidence: 99%

“…TMK = melting point (K). DB = solubility parameter of Ruelle [16]. MAXW = the greatest value of KAccW(i) or KDonW(i) in water.…”

Section: Solubility In Water: Watsolumentioning

confidence: 99%

Section: Octanol-water Partition Coefficient: Tdklow Programmentioning

confidence: 99%

Section: ) -σN Oh (J)*(boh + Rw -Ro))/ln10 (13) ∆Acc = σVacc(i)*(logmentioning

confidence: 99%

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Estimation of vapour pressure, solubility in water, Henry’s law function, and Log Kow as a function of temperature for prediction of the environmental fate of chemicals

Paasiv́irta¹

2006

WIT Transactions on Biomedicine and Health, Vol 10

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Prediction of the n‐hexane/water and 1‐octanol/water partition coefficients for environmentally relevant compounds using molecular simulation

Garrido

Economou²,

Queimada

et al. 2011

AIChE Journal

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In recent years molecular simulation has emerged as a useful tool to predict physical properties of complex chemical systems. A methodology to estimate the n‐hexane/water and 1‐octanol/water partition coefficients of environmentally relevant solutes, namely substituted alkyl‐aromatic molecules, chlorobenzenes, polychlorinated biphenyls (PCBs) and polychlorinated diphenyl ethers (PCDEs) using molecular simulation is elucidated here. The partition coefficients are calculated based on the absolute solvation Gibbs energies in each phase which are estimated from molecular dynamics simulations employing the thermodynamic integration approach. Very encouraging results, with average absolute deviations of 0.4 log P units are presented. Consequently, this molecular‐based approach with a strong physical background can provide reliable prediction of the partition coefficients in different solvent pairs without the a priori knowledge of experimental data. © 2011 American Institute of Chemical Engineers AIChE J, 58: 1929–1938, 2012

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Evaluation of Lignans from Piper cubeba against Schistosoma mansoni Adult Worms: A Combined Experimental and Theoretical Study

Parreira

Costa

Heleno

et al. 2018

Chemistry & Biodiversity

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Six dibenzylbutyrolactonic lignans ((−)‐hinokinin (1), (−)‐cubebin (2), (−)‐yatein (3), (−)‐5‐methoxyyatein (4), dihydrocubebin (5) and dihydroclusin (6)) were isolated from Piper cubeba seed extract and evaluated against Schistosoma mansoni. All lignans, except 5, were able to separate the adult worm pairs and reduce the egg numbers during 24 h of incubation. Lignans 1, 3 and 4 (containing a lactone ring) were the most efficient concerning antiparasitary activity. Comparing structures 3 and 4, the presence of the methoxy group at position 5 appears to be important for this activity. Considering 1 and 3, it is possible to see that the substitution pattern change (methylenedioxy or methoxy groups) in positions 3′ and 4′ alter the biological response, with 1 being the second most active compound. Computational calculations suggest that the activity of compound 4 can be correlated with the largest lipophilicity value.

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The n-octanol and n-hexane/water partition coefficient of environmentally relevant chemicals predicted from the mobile order and disorder (MOD) thermodynamics

Cited by 93 publications

References 117 publications

Estimation of vapour pressure, solubility in water, Henry’s law function, and Log Kow as a function of temperature for prediction of the environmental fate of chemicals

Estimation of vapour pressure, solubility in water, Henry’s law function, and Log Kow as a function of temperature for prediction of the environmental fate of chemicals

Prediction of the n‐hexane/water and 1‐octanol/water partition coefficients for environmentally relevant compounds using molecular simulation

Evaluation of Lignans from Piper cubeba against Schistosoma mansoni Adult Worms: A Combined Experimental and Theoretical Study

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