chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

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

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

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 sp ...

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 substa ...

), in dilute solution in the noncoordinating solvent 1,2-dichloroethane with a zero DN. The units are

kilocalorie The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of on ...

s per

mole Mole (or Molé) may refer to: Animals * Mole (animal) or "true mole", mammals in the family Talpidae, found in Eurasia and North America * Golden moles, southern African mammals in the family Chrysochloridae, similar to but unrelated to Talpida ...

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

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

solvate Solvation (or dissolution) describes the interaction of a solvent with dissolved molecules. Both ionized and uncharged molecules interact strongly with a solvent, and the strength and nature of this interaction influence many properties of the ...

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 clas ...

14.1 kcal/mol (59.0 kJ/mol) *

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

17 kcal/mol (71 kJ/mol) *

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

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 ma ...

20 kcal/mol (84 kJ/mol) *

dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the maj ...

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

dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...

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

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

31.5 kcal/mol (132 kJ/mol) *

pyridine Pyridine is a basic 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, weakly alkaline, water-miscible liquid with a d ...

33.1 kcal/mol (138 kJ/mol) *

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA ...

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 perturbed 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 consists 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 complexing agents. Many ...

. 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 concept is a jargon for "hard and soft Lewis acids and bases, (Lewis) acids and bases". HSAB is widely used in chemistry for explaining stability of chemical compound, compounds, reaction mechanisms and pathways. It assigns the terms 'hard' o ...

, the two properties are hardness and strength, while for Drago’s quantitative ECW model, the two properties are electrostatic and covalent.

References

Further reading