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Donor number

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Acids and bases

Acceptor number Acid Acid–base reaction Acid–base homeostasis Acid strength Acidity function Amphoterism Base Buffer solutions Dissociation constant Donor number Equilibrium chemistry Extraction Hammett acidity function pH Proton affinity Self-ionization of water Titration Lewis acid catalysis Frustrated Lewis pair Chiral Lewis acid ECW model
Acid types
Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid
Base types
Brønsted–Lowry Lewis Organic Oxide Strong Superbases Non-nucleophilic Weak
v t e

Inchemistryadonor number (DN) is a quantitative measure of Lewis basicity. A donor number is defined as the negative enthalpy value for the 1:1 adduct formation between a Lewis base and the standard Lewis acid SbCl₅ (antimony pentachloride), in dilute solution in the noncoordinating solvent 1,2-dichloroethane with a zero DN. The units are kilocalories per mole for historical reasons.^[1] The donor number is a measure of the ability of a solventtosolvate cations and Lewis acids. The method was developed by V. Gutmann in 1976.^[2] Likewise Lewis acids are characterized by acceptor numbers (AN, see Gutmann–Beckett method).

Typical solvent values are:^[3]

acetonitrile 14.1 kcal/mol (59.0 kJ/mol)
acetone 17 kcal/mol (71 kJ/mol)
methanol 19 kcal/mol (79 kJ/mol)
tetrahydrofuran 20 kcal/mol (84 kJ/mol)
dimethylformamide (DMF) 26.6 kcal/mol (111 kJ/mol)
dimethyl sulfoxide (DMSO) 29.8 kcal/mol (125 kJ/mol)
ethanol 31.5 kcal/mol (132 kJ/mol)
pyridine 33.1 kcal/mol (138 kJ/mol)
triethylamine 61 kcal/mol (255 kJ/mol)

The donor number of a solvent can be measured via calorimetry, although it is frequently measured with nuclear magnetic resonance (NMR) spectroscopy using assumptions on complexation.^[4] A critical review of the donor number concept has pointed out the serious limitations of this affinity scale.^[5] 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.^[6] For Pearson qualitative HSAB theory, the two properties are hardness and strength,^[7] while for Drago's quantitative ECW model, the two properties are electrostatic and covalent.^[8]

References[edit]

^ Françoise Arnaud-neu; Rita Delgado; Sílvia Chaves (2003). "Critical evaluation of stability constants and thermodynamic functions of metal complexes of crown ethers". Pure Appl. Chem. 75 (1): 71–102. doi:10.1351/pac200375010071. S2CID 97549495.

^ V. Gutmann (1976). "Solvent effects on the reactivities of organometallic compounds". Coord. Chem. Rev. 18 (2): 225–255. doi:10.1016/S0010-8545(00)82045-7.

^ D.T. Sawyer, J.L. Roberts (1974). Experimental Electrochemistry for Chemists. John Wiley & Sons, Inc.

^ KATAYAMA, Misaki; SHINODA, Mitsushi; OZUTSUMI, Kazuhiko; FUNAHASHI, Shigenobu; INADA, Yasuhiro (2012). "Reevaluation of Donor Number Using Titration Calorimetry". Analytical Sciences. 28 (2): 103–106. doi:10.2116/analsci.28.103. ISSN 0910-6340. PMID 22322801.

^ Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) p 51 ISBN 978-0-470-74957-9

^ Cramer, R. E., and Bopp, T. T. (1977) Great E and C plot. Graphical display of the enthalpies of adduct formation for Lewis acids and bases. Journal of Chemical Education 54 612–613. doi:10.1021/ed054p612

^ Pearson, Ralph G. (1968). "Hard and soft acids and bases, HSAB, part 1: Fundamental principles". J. Chem. Educ. 1968 (45): 581–586. Bibcode:1968JChEd..45..581P. doi:10.1021/ed045p581.

^ Vogel G. C.; Drago R. S (1996). "The ECW Model". Journal of Chemical Education. 73 (8): 701–707. Bibcode:1996JChEd..73..701V. doi:10.1021/ed073p701.