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 176-200 of 210

NameFormulaAcceptor number
AN
Donor number
DN
🏷 Tag
N-bis(dimethylamino)phosphoryl-N-ethylethanamineC8H22N3OP37.8
2-methyl-2-propanolC4H10O27.138.0alcohol;
N-(dimethylamino-pyrrolidin-1-ylphosphoryl)-N-methylmethanamineC8H20N3OP38.0
hexamethylphosphoramideC6H18N3OP10.638.8
3-methylpyridineC6H7N39.0heteroaromatic;
dimethyl sulfideC2H6S(0.0)40.0
piperidineC5H11N(4.8)40.0amine;
bis(diethylamino)-pyrrolidinophosphine oxideC12H28N3OP40.2
bis(ethylamino)-(dimethylamino)phosphine oxideC6H18N3OP40.6
1-di(piperidin-1-yl)phosphorylpiperidineC15H30N3OP40.9
diethyl sulfideC4H10S(5.2)41.0
N-(azetidin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC7H18N3OP41.1
bis(dimethylamino)-(ethylamino)phosphine oxideC6H18N3OP41.2
butylamineC4H11N(8.8)42.0amine;
N,N,1,3-tetramethyl-1,3,2-diazaphospholidin-2-amine 2-oxideC6H16N3OP42.1
dimethylamino-di(azetidin-1-yl)phosphine oxideC8H18N3OP42.3
ethylamino-dipyrrolidinophosphine oxideC10H22N3OP42.6
tri(azetidin-1-yl)phosphine oxideC9H18N3OP43.0
2-methyl-2-butanolC5H12O(15.4)44.0alcohol;
hydrazineH4N244.0
N-dipyrrolidin-1-ylphosphoryl-N-methylmethanamineC10H22N3OP45.4
tripyrrolidinophosphine oxideC12H24N3OP47.2
N-bis(ethylamino)phosphorylethanamineC6H18N3OP47.3
N-(aziridin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC6H16N3OP48.6
N-[bis(aziridin-1-yl)phosphoryl]-N-methylmethanamineC6H14N3OP49.1