Gutmann acceptor and donor numbers

The Gutmann Acceptor- (AN) and Donor Number (DN) are measures of the strength of solvents as Lewis acids or bases.
The Acceptor Number is based on the 31P-NMR chemical shift of triethylphosphine oxide in the solvent.
The Donor Number is based on the heat of reaction between the compound dissolved in CH2ClCH2Cl and SbCl5, and is therefore a 'solute' rather than a 'solvent' scale. Because SbCl5 is decomposed by protic compounds, e.g. alcohols, the Donor Numbers for these have to be determined by indirect methods.

The Acceptor Number is a measure of hydrogen bond acidity and correlated with other hydrogen bond acidity scales such as → Dimroth-Reichardt ET (→ ET vs AN) and → Swain Acity (→ Acity vs AN). Correlation with → Kamlet-Taft α and → Catalán SA is weaker.
The Donor Number is correlated with → Kamlet-Taft β (→ β vs DN).

See → "The donor-acceptor approach to molecular interactions" by V. Gutmann, Plenum Press, New York and London (1978), and →Lewis donor strength for scales of Lewis bases.

Note: AN values in parenthesis are estimated from the corresponding Dimroth-Reichardt ET-values.

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NameFormulaAcceptor number
AN
Donor number
DN
🏷 Tag
ethyl chloroformateC3H5ClO221.3halo; ester
oxaneC5H10O(6.9)22.0ether
N,N-dimethylurethaneC5H11NO222.4amide; ester
diphenylphosphinic chlorideC12H10ClOP22.4
diphenylphosphonic chloride22.4
2-phenylethanolC8H10O33.823.0aromatic; alcohol
benzyl alcoholC7H8O36.823.0aromatic; alcohol
trimethyl phosphateC3H9O4P16.323.0
tributyl phosphateC12H27O4P9.923.7
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octaneC10H18O(2.0)24.0ether
formamideCH3NO39.824.0amide
cyclohexanolC6H12O(26.3)25.0alcohol
pentanolC5H12O(30.5)25.0alcohol
triethyl phosphateC6H15O4P(16.5)26.0
N,N-dimethylformamideC3H7NO16.026.6amide
N,N-dimethylanilineC8H11N(6.7)27.0amine; aromatic
N-methylformamideC2H5NO32.127.0amide
1-methylazepan-2-oneC7H13NO(16.3)27.1amide
N-methylpyrrolidoneC5H9NO13.327.3amide
1,3-dimethyl-2-imidazolidinoneC5H10N2O(18.0)27.7amide
N,N-dimethylacetamideC4H9NO13.627.8amide
trimethylureaC4H10N2O29.3
diethyl dimethylamidophosphateC6H16NO3P29.5
diethyl dimethylphosphoramidate     ⋮29.5
1,3-dimethylureaC3H8N2O29.7