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.

Lines 151-175 of 210

NameFormulaAcceptor number
AN
Donor number
DN
🏷 Tag
dimethyl sulfoxideC2H6OS19.329.8
hexanolC6H14O(29.9)30.0alcohol;
dioctyl sulfoxideC16H34OS30.3
N,N-diethylformamideC5H11NO(16.7)30.9amide;
2-chloroanilineC6H6ClN(23.7)31.0aromatic; halo; amine;
decanolC10H22O(27.8)31.0alcohol;
dibutyl sulfoxideC8H18OS31.0
N,N,N',N'-tetramethylureaC5H12N2O9.231.0amide;
dioctyl methylphosphonateC17H37O3P31.2
3-methyl-1-butanolC5H12O(30.3)32.0alcohol;
octanolC8H18O(29.0)32.0alcohol;
quinolineC9H7N(12.2)32.0aromatic; heteroaromatic;
N,N-diethylacetamideC6H13NO13.632.2amide;
1,3-dimethyltetrahydropyrimidin-2(1H)-oneC6H12N2O(17.3)33.0amide;
N-methylanilineC7H9N(18.0)33.0amine; aromatic;
pyridineC5H5N14.233.1heteroaromatic;
trioctylphosphine oxideC24H51OP33.8
4-methylpyridineC6H7N(12.6)34.0heteroaromatic;
pyridine N-oxideC5H5NO34.4heteroaromatic;
anilineC6H7N(21.4)35.0aromatic; amine;
tert-butyl acetateC6H12O235.9ester;
4-methylpyridine N-oxideC6H7NO36.3heteroaromatic;
N-(dimethylamino-ethoxyphosphoryl)-N-methylmethanamineC6H17N2O2P36.4
hexaethylphosphoramideC12H30N3OP36.6
2-methyl-1-propanolC4H10O(29.5)37.0alcohol;