ABSTRACT

Hydrophobicity values (log Po/w) determined both by potentiometry and by the conventional shake-flask method and aqueous pKa values obtained by potentiometry for seven isoniazid and nine benzimidazole derivatives are presented. Several of these compounds have strong hydrophilic or hydrophobic character, and some of them show two or more ionizable sites, sometimes very acidic or very basic. These facts have compelled us to work near the limits of the potentiometric technique, and therefore, a critical evaluation of the results obtained in these extreme working conditions is presented. Particularly, details about the potentiometric determination of log Po/w values of the most hydrophilic and most hydrophobic compounds are clearly described.

Compounds

#	Formula	Name
1	C6H7N3O	isonicotinic acid hydrazide
2	C6H9N5O	2-hydrazinyl-4-pyridinecarboxylic acid hydrazide
3	C8H9N3O2	4-pyridinecarboxylic acid, 2-acetylhydrazide
4	C16H25N3O2	4-pyridinecarboxylic acid, 2-(1-oxodecyl)hydrazide
5	C11H13N3O	4-pyridinecarboxylic acid, 2-cyclopentylidenehydrazide
6	C12H15N3O	4-pyridinecarboxylic acid, 2-cyclohexylidenehydrazide
7	C13H17N3O	4-pyridinecarboxylic acid, 2-(4-methylcyclohexylidene)hydrazide
8	C9H10N2S	2-(ethylthio)-1H-benzimidazole
9	C11H14N2S	1-ethyl-2-(ethylthio)-1H-benzimidazole
10	C10H12N2S	2-[(1-methylethyl)thio]-1H-benzimidazole
11	C15H20N2S	2-[(2-cyclohexylethyl)thio]-1H-benzimidazole
12	C14H12N2S	2-[(phenylmethyl)thio]-1H-benzimidazole
13	C20H16N2S	2-[(diphenylmethyl)thio]-1H-benzimidazole
14	C14H10N4O4S	2-[[(3,5-dinitrophenyl)methyl]thio]-1H-benzimidazole
15	C7H6N2S	2-benzimidazolethiol
16	C8H18O	octan-1-ol
17	H2O	water

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	Phase	Method	#Points
POMD	1 16 17	Amount concentration (molarity), mol/dm3 - 1 ; Liquid mixture 1	Mole fraction - 1; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	1 16 17	Amount concentration (molarity), mol/dm3 - 1 ; Liquid mixture 1	Mole fraction - 1; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 2	Amount concentration (molarity), mol/dm3 - 2 ; Liquid mixture 1	Mole fraction - 2; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Potentiometric	1
POMD	16 17 2	Amount concentration (molarity), mol/dm3 - 2 ; Liquid mixture 1	Mole fraction - 2; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 3 17	Amount concentration (molarity), mol/dm3 - 3 ; Liquid mixture 1	Mole fraction - 3; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 3 17	Amount concentration (molarity), mol/dm3 - 3 ; Liquid mixture 1	Mole fraction - 3; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 17 4	Amount concentration (molarity), mol/dm3 - 4 ; Liquid mixture 1	Mole fraction - 4; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Potentiometric	1
POMD	16 17 4	Amount concentration (molarity), mol/dm3 - 4 ; Liquid mixture 1	Mole fraction - 4; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 5 17	Amount concentration (molarity), mol/dm3 - 5 ; Liquid mixture 1	Mole fraction - 5; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 5 17	Amount concentration (molarity), mol/dm3 - 5 ; Liquid mixture 1	Mole fraction - 5; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 6	Amount concentration (molarity), mol/dm3 - 6 ; Liquid mixture 1	Mole fraction - 6; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Potentiometric	1
POMD	16 17 6	Amount concentration (molarity), mol/dm3 - 6 ; Liquid mixture 1	Mole fraction - 6; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 7	Amount concentration (molarity), mol/dm3 - 7 ; Liquid mixture 1	Mole fraction - 7; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Potentiometric	1
POMD	16 17 7	Amount concentration (molarity), mol/dm3 - 7 ; Liquid mixture 1	Mole fraction - 7; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 8	Amount concentration (molarity), mol/dm3 - 8 ; Liquid mixture 1	Mole fraction - 8; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 17 8	Amount concentration (molarity), mol/dm3 - 8 ; Liquid mixture 1	Mole fraction - 8; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 9	Amount concentration (molarity), mol/dm3 - 9 ; Liquid mixture 1	Mole fraction - 9; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Protentiometric	1
POMD	16 17 9	Amount concentration (molarity), mol/dm3 - 9 ; Liquid mixture 1	Mole fraction - 9; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 10	Amount concentration (molarity), mol/dm3 - 10 ; Liquid mixture 1	Mole fraction - 10; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Protentiometric	1
POMD	16 17 10	Amount concentration (molarity), mol/dm3 - 10 ; Liquid mixture 1	Mole fraction - 10; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 11	Amount concentration (molarity), mol/dm3 - 11 ; Liquid mixture 1	Mole fraction - 11; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Protentiometric	1
POMD	16 17 12	Amount concentration (molarity), mol/dm3 - 12 ; Liquid mixture 1	Mole fraction - 12; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Protentiometric	1
POMD	16 17 12	Amount concentration (molarity), mol/dm3 - 12 ; Liquid mixture 1	Mole fraction - 12; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 17 13	Amount concentration (molarity), mol/dm3 - 13 ; Liquid mixture 1	Mole fraction - 13; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 17 14	Amount concentration (molarity), mol/dm3 - 14 ; Liquid mixture 1	Mole fraction - 14; Liquid - 17 Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 17 14	Amount concentration (molarity), mol/dm3 - 14 ; Liquid mixture 1	Mole fraction - 14; Liquid - 17 Pressure, kPa; Liquid mixture 1 Temperature, K; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1
POMD	16 15 17	Amount concentration (molarity), mol/dm3 - 15 ; Liquid mixture 1	Mole fraction - 15; Liquid - 17 Pressure, kPa; Liquid mixture 1 Temperature, K; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Pontentiometric	1
POMD	16 15 17	Amount concentration (molarity), mol/dm3 - 15 ; Liquid mixture 1	Mole fraction - 15; Liquid - 17 Pressure, kPa; Liquid mixture 1 Temperature, K; Liquid mixture 1	Liquid mixture 1 Liquid - 17	Shake-Flask	1

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

Acidity and Hydrophobicity of Several New Potential Antitubercular Drugs: Isoniazid and Benzimidazole Derivatives

Rafols, C.[Clara], Bosch, E.[Elisabeth], Ruiz, R.[Rebeca], Box, K. J.[Karl J.], Reis, M.[Marina], Ventura, C.[Cristina], Santos, S.[Susana], Araujo, M. E., Martins, F.[Filomena]

ABSTRACT