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 → Catal├ín 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
1,1,1,3,3,3-hexafluoro-2-propanolC3H2F6O66.7halo; alcohol;
1,1-dichloroethaneC2H4Cl216.2halo;
1,2,3-propanetriolC3H8O3(45.4)19.0alcohol;
1,2-diaminoethaneC2H8N220.955.0amine;
1,2-dichlorobenzeneC6H4Cl2(9.5)3.0aromatic; halo;
1,2-dichloroethaneC2H4Cl216.70.0halo;
1,2-dimethoxyethaneC4H10O210.220.0ether;
1,3,2-dioxathiolan-2-oxideC2H4O3S15.3
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octaneC10H18O(2.0)24.0ether;
1,3,5-trimethylbenzeneC9H12(0.0)10.0aromatic;
1,3-dichlorobenzeneC6H4Cl2(7.1)2.0aromatic; halo;
1,3-dimethyl-2-imidazolidinoneC5H10N2O(18.0)27.7amide;
1,3-dimethylbenzeneC8H10(0.7)5.0aromatic;
1,3-dimethyltetrahydropyrimidin-2(1H)-oneC6H12N2O(17.3)33.0amide;
1,3-dimethylureaC3H8N2O29.7
1,3-dioxolan-2-oneC3H4O3(29.5)16.4ester;
1,3-dioxolaneC3H6O2(19.2)21.2
1,4-dimethylbenzeneC8H10(0.3)5.0aromatic;
1-di(piperidin-1-yl)phosphorylpiperidineC15H30N3OP40.9
1-methylazepan-2-oneC7H13NO(16.3)27.1amide;
1-methylpyrrolidin-2-thioneC5H9NS17.7
2,2,2-trifluoro-N,N-dimethylacetamideC4H6F3NO16.6amide; fluoro;
2,2,2-trifluoroethanolC2H3F3O53.8halo; alcohol;
2,2,4,4-tetramethyl-3-pentanoneC9H18O10.3ketone;
2,2,4-trimethylpentan-3-oneC8H16O11.3ketone;