Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Octanol/Water Partition Coefficients of Sulfonamides: Experimental Determination and Calculation Using Physicochemical Descriptors

Raevsky, O. A.[Oleg A.], Perlovich, G. L.[German L.], Kazachenko, V. P.[Vladimir P.], Strakhova, N.[Nadezda], Schaper, K.-J.[Klaus-J.]
J. Chem. Eng. Data 2009, 54, 11, 3121-3124
ABSTRACT
1-Octanol/water partition coefficients log Kow of 38 sulfonamides were determined by the isothermal saturation method. These values were used both for direct correlation and as test data for the verification of a regression equation for calculation of log Kow on the basis of two physicochemical descriptors (molecular polarizability, a surrogate for molecular size, and H-bond acceptor ability). Comparison of experimental and calculated Kow values demonstrated the wide applicability of those equations.
Compounds
# Formula Name
1 C12H10ClNO2S N-(2-chlorophenyl)benzenesulfonamide
2 C12H9Cl2NO2S N-(2,3-dichlorophenyl)benzenesulfonamide
3 C12H10ClNO2S N-(4-chlorophenyl)benzenesulfonamide
4 C12H10N2O4S N-(4-nitrophenyl)benzenesulfonamide
5 C12H9Br2NO2S N-(2,4-dibromophenyl)benzenesulfonamide
6 C12H10N2O4S N-(2-nitrophenyl)benzenesulfonamide
7 C11H9ClN2O2S N-(3-chloro-2-pyridinyl)benzenesulfonamide
8 C11H9ClN2O2S N-(2-chloro-3-pyridinyl)benzenesulfonamide
9 C14H14N2O4S ethyl 6-(phenylsulfonamido)nicotinate
10 C14H14N2O5S N-(4-ethoxyphenyl)-4-nitrobenzenesulfonamide
11 C9H7N3O4S2 4-nitro-N-2-thiazolylbenzenesulfonamide
12 C13H12N4O5S N-[3-[[(4-nitrophenyl)sulfonyl]amino]-4-pyridinyl]-acetamide
13 C12H11N3O4S N-(5-methylpyridin-2-yl)-4-nitrobenzenesulfonamide
14 C12H11N3O4S 4-amino-N-(4-nitrophenyl)benzenesulfonamide
15 C14H16N2O2S 4-amino-N-(4-ethylphenyl)benzenesulfonamide
16 C12H11IN2O2S 4-amino-N-(4-iodophenyl)benzenesulfonamide
17 C13H14N2O3S 4-amino-N-(4-methoxyphenyl)benzenesulfonamide
18 C13H11N3O2S 4-amino-N-(4-cyanophenyl)benzenesulfonamide
19 C12H11ClN2O2S 4-amino-N-(4-chlorophenyl)benzenesulfonamide
20 C12H10Cl2N2O2S 4-amino-N-(2,3-dichlorophenyl)benzenesulfonamide
21 C12H10Cl2N2O2S 4-amino-N-(3,4-dichlorophenyl)benzenesulfonamide
22 C12H10Cl2N2O2S 4-amino-N-(2,5-dichlorophenyl)benzenesulfonamide
23 C12H9Cl3N2O2S 4-amino-N-(2,4,5-trichlorophenyl)benzenesulfonamide
24 C13H13ClN2O2S 4-amino-N-(5-chloro-2-methylphenyl)benzenesulfonamide
25 C13H13ClN2O2S 4-amino-N-(2-chloro-4-methylphenyl)benzenesulfonamide
26 C13H13ClN2O2S 4-amino-N-(4-chloro-2-methylphenyl)benzenesulfonamide
27 C13H13ClN2O2S 4-amino-N-(3-chloro-4-methylphenyl)benzenesulfonamide
28 C13H13ClN2O3S 4-amino-N-(3-chloro-2-methoxyphenyl)benzenesulfonamide
29 C12H10BrN3O4S 4-amino-N-(2-bromo-4-nitrophenyl)benzenesulfonamide
30 C10H14N2O4S ethyl ((4-aminophenyl)sulfonyl)glycinate
31 C10H16N2O2S 4-amino-N,N-diethylbenzenesulfonamide
32 C8H12N2O2S 4-amino-N,N-dimethylbenzenesulfonamide
33 C7H10N2O2S 4-amino-N-methylbenzenesulfonamide
34 C13H13ClN2O2S 4-amino-N-(4-chlorophenyl)-2-methylbenzenesulfonamide
35 C12H10Cl2N2O2S 4-amino-2-chloro-N-(2-chlorophenyl)benzenesulfonamide
36 C13H13ClN2O2S 4-amino-N-(2-chlorophenyl)-2-methylbenzenesulfonamide
37 C12H10Cl2N2O2S 4-amino-2-chloro-N-(4-chlorophenyl)benzenesulfonamide
38 C13H13N3O4S 4-amino-2-methyl-N-(2-nitrophenyl)benzenesulfonamide
39 H2O water
40 C8H18O octan-1-ol
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 40
  • 39
  • 1
  • Amount concentration (molarity), mol/dm3 - 1 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 1; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 2
  • Amount concentration (molarity), mol/dm3 - 2 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 2; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 3
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 3; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 4
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 4; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 5
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 5; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 6
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 6; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 7
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 7; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 8
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 8; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 9
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 9; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 10
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 10; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 11
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 11; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 12
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 12; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 13
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 13; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 14
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 14; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 15
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 15; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 16
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 16; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 17
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 17; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 18
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 18; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 19
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 19; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 20
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 20; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 21
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 21; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 22
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 22; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 23
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 23; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 24
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 24; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 25
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 25; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 26
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 26; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 27
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 27; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 28
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 28; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 29
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 29; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 30
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 30; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 31
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 31; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 32
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 32; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 33
  • 39
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 33; Liquid - 39
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 34
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 34; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 35
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 35; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 36
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 36; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 37
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 37; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1
  • POMD
  • 40
  • 39
  • 38
  • Amount concentration (molarity), mol/dm3 - 39 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Mole fraction - 38; Liquid mixture 1
  • Liquid mixture 1
  • Liquid - 39
  • SPECTR
  • 1