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 223

NameFormulaAcceptor number
AN
Donor number
DN
🏷 Tag
triethyl phosphateC6H15O4P(16.5)26.0
diethyl dimethylamidophosphateC6H16NO3P29.5
diethyl dimethylphosphoramidate     ⋮29.5
N,N,1,3-tetramethyl-1,3,2-diazaphospholidin-2-amine 2-oxideC6H16N3OP42.1
N-(aziridin-1-yl-dimethylaminophosphoryl)-N-methylmethanamine     ⋮48.6
N-(dimethylamino-ethoxyphosphoryl)-N-methylmethanamineC6H17N2O2P36.4
bis(dimethylamino)-(ethylamino)phosphine oxideC6H18N3OP41.2
bis(ethylamino)-(dimethylamino)phosphine oxide     ⋮40.6
hexamethylphosphoramide     ⋮10.638.8
N-bis(ethylamino)phosphorylethanamine     ⋮47.3
benzoyl chlorideC7H5ClO2.3
benzoyl fluorideC7H5FO2.0
benzonitrileC7H5N15.511.9aromatic; nitrile;
benzaldehydeC7H6O16.0aromatic; aldehyde;
tolueneC7H8(1.8)0.1aromatic;
3-methylphenolC7H8O50.4
benzyl alcohol     ⋮36.823.0aromatic; alcohol;
methoxybenzene     ⋮(7.8)9.0aromatic; ether;
N-methylanilineC7H9N(18.0)33.0amine; aromatic;
1-methylazepan-2-oneC7H13NO(16.3)27.1amide;
2,2-dimethylpentan-3-oneC7H14O14.6ketone;
2,4-dimethyl-3-pentanone     ⋮(10.9)16.2ketone;
ethyl 2,2-dimethylpropanoateC7H14O213.0ester;
heptaneC7H160.00.0alkane;
N-(azetidin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC7H18N3OP41.1