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The solubility of a solute (= solved compound) highly depends on its properties (e.g. its polarity)
and the properties of the solvent as well as on the temperature, the pressure and the pH
(„Like dissolves like“). A substance can be solved up to a specific and solute- and solvent
dependent maximum concentration (=saturation concentration).
Polarity describes the electric charge distribution within a molecules, which is dependent on
the electronegativity of its containing atoms. Polar molecules can form e.g. hydrogen bonds
(compare slides „Polarity Basics“)
e.g. O δ+ δ− δ+ δ+ δ−
Water H C O H H C C N
Decreasing
Methanol H Hδ+
δ+
Ethanol Water H H
Acetonitrile Methanol Acetonitrile
dielectric constant
Chloroform
Toluene δ−
Cl C H H C C C C C C H
Hexane
Cl H H H H H H
δ−
Chloroform Toluene Hexane
logD calculation and drawing of chemical structures was performed with „MarvinSketch 14.8.25.0“, ChemAxon (www.chemaxon.com)
PD Dr. J. Graßmann; PD Dr. T. Letzel
Lehrstuhl für Siedlungswasserwirtschaft
Ingenieurfakultät Bau Geo Umwelt
Technische Universität München
Partition coefficient
log P refers to neutral, non-ionizable molecule species
Lipophilicity/hydrophilicity of a molecules is determined according to its distribution in a
biphasic system, consisting of two immiscible solvents (e.g. octanol and water)
Distribution coefficient
log D refers to ionizable molecules (Lipophilicity and therefore solubility changes as a
function of pH for ionisable compounds)
Distribution coefficient (log D) =
pH reflects the concentration of hydrogen ions (H+)/hydroxyl ions (OH-) in the solution.
The proton (i.e. H+) concentration increases with decreasing pH.
H+ + OH− ⇋ H2O
pH 0 7 14
Hydrogen ion concentration [H+] 100 10-7 10-14
H+
OH-
pKa is the pH at which the abundance of ionized and non-ionized from is equal
e.g. acetic acid (CH3COOH) with a pKa of 4.8
H O H O
- -
- -
H-C-C H-C-C -
H OH H O
100
Abundance [%]
50
0
4.8
Protonisation of carboxylgroup Deprotonisation of carboxylgroup
at low pH, i.e. high H+ concentration pH of solution at high pH, i.e. low H+ concentration
Molecule is neutral Molecule is negatively charged
Majority is positively
Adrenaline charged at pH 7.4 -1.63
+
Vitamine A 4.69
Neutral at pH 7.4
logD calculation and drawing of chemical structures was performed with „MarvinSketch 14.8.25.0“, ChemAxon (www.chemaxon.com)
PD Dr. J. Graßmann; PD Dr. T. Letzel
Lehrstuhl für Siedlungswasserwirtschaft
Ingenieurfakultät Bau Geo Umwelt
Technische Universität München
pI is the pH at which a molecule carries no net electrical charge. At a pH below the pI, the
molecule will carry a positive charge. At a pH above the pI, it will carry a negative charge.
e.g. amino acid alanine (pI = 6.0)
e.g. ethanol,
Vitamin D3 7.13 acetone, DMSO,
„fat soluble“ chloroform
logD calculation and drawing of chemical structures was performed with „MarvinSketch 14.8.25.0“, ChemAxon (www.chemaxon.com)
PD Dr. J. Graßmann; PD Dr. T. Letzel
Lehrstuhl für Siedlungswasserwirtschaft
Ingenieurfakultät Bau Geo Umwelt
Technische Universität München
e.g. water,
Vitamin B7 -2.57
ethanol
„water soluble“
good solubility
at high pH due to
2 negative charges alkaline
-3.67 solution
logD calculation and drawing of chemical structures was performed with „MarvinSketch 14.8.25.0“, ChemAxon (www.chemaxon.com)
PD Dr. J. Graßmann; PD Dr. T. Letzel
Lehrstuhl für Siedlungswasserwirtschaft
Ingenieurfakultät Bau Geo Umwelt
Technische Universität München
Solvent properties
properties
- Temperature
- Pressure
The effect of pressure on the solubility is only minor and is therefore negligible