chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

a donor number (DN) is a quantitative measure of Lewis basicity. A donor number is defined as the negative

enthalpy Enthalpy () is the sum of a thermodynamic system's internal energy and the product of its pressure and volume. It is a state function in thermodynamics used in many measurements in chemical, biological, and physical systems at a constant extern ...

value for the 1:1 adduct formation between a Lewis base and the standard

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...

SbCl₅ (

antimony pentachloride Antimony pentachloride is a chemical compound with the formula SbCl5. It is a colourless oil, but typical samples are yellowish due to dissolved chlorine. Owing to its tendency to hydrolyse to hydrochloric acid, SbCl5 is a highly corrosive subs ...

), in dilute solution in the noncoordinating solvent

1,2-dichloroethane The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...

with a zero DN. The units are

kilocalorie The calorie is a unit of energy that originated from the caloric theory of heat. The large calorie, food calorie, dietary calorie, kilocalorie, or kilogram calorie is defined as the amount of heat needed to raise the temperature of one liter of w ...

s per

mole Mole (or Molé) may refer to: Animals * Mole (animal) or "true mole" * Golden mole, southern African mammals * Marsupial mole Marsupial moles, the Notoryctidae family, are two species of highly specialized marsupial mammals that are found i ...

for historical reasons. The donor number is a measure of the ability of a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

to solvate

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

s and Lewis acids. The method was developed by V. Gutmann in 1976. Likewise Lewis acids are characterized by acceptor numbers (AN, see

Gutmann–Beckett method In chemistry, the Gutmann–Beckett method is an experimental procedure used by chemists to assess the Lewis acidity of molecular species. Triethylphosphine oxide (, TEPO) is used as a probe molecule and systems are evaluated by 31P-NMR spectr ...

). Typical

values are: *

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...

14.1 kcal/mol (59.0 kJ/mol) *

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

17 kcal/mol (71 kJ/mol) *

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

19 kcal/mol (79 kJ/mol) *

tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...

20 kcal/mol (84 kJ/mol) *

dimethylformamide Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...

(DMF) 26.6 kcal/mol (111 kJ/mol) *

dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is ...

(DMSO) 29.8 kcal/mol (125 kJ/mol) *

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

31.5 kcal/mol (132 kJ/mol) *

pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...

33.1 kcal/mol (138 kJ/mol) *

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. Like triethanolamine and the tetraethylammonium ion, it is often abbreviated TEA. It is a colourless volatile liquid with a strong fishy odor remini ...

61 kcal/mol (255 kJ/mol) The donor number of a solvent can be measured via

calorimetry In chemistry and thermodynamics, calorimetry () is the science or act of measuring changes in '' state variables'' of a body for the purpose of deriving the heat transfer associated with changes of its state due, for example, to chemical reac ...

, although it is frequently measured with

nuclear magnetic resonance Nuclear magnetic resonance (NMR) is a physical phenomenon in which nuclei in a strong constant magnetic field are disturbed by a weak oscillating magnetic field (in the near field) and respond by producing an electromagnetic signal with a ...

(NMR) spectroscopy using assumptions on

complexation A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or ...

. A critical review of the donor number concept has pointed out the serious limitations of this affinity scale. Furthermore, it has been shown that to define the order of Lewis base strength (or Lewis acid strength) at least two properties must be considered. For Pearson qualitative

HSAB theory HSAB is an acronym for "hard and soft (Lewis) acids and bases". HSAB is widely used in chemistry for explaining the stability of compounds, reaction mechanisms and pathways. It assigns the terms 'hard' or 'soft', and 'acid' or 'base' to chemical ...

, the two properties are hardness and strength, while for Drago's quantitative

ECW model In chemistry, the ECW model is a semi-quantitative model that describes and predicts the strength of Lewis acid–Lewis base interactions. Many chemical reactions can be described as acid–base reactions, so models for such interactions are of pot ...

, the two properties are electrostatic and covalent.

References

Further reading