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
diethyl carbonateC5H10O3(7.7)16.0ester
propyl acetateC5H10O2(8.6)16.0ester
propanenitrileC3H5N(20.1)16.1nitrile
2-methylpentan-3-oneC6H12O16.2ketone
2,4-dimethyl-3-pentanoneC7H14O(10.9)16.2ketone
2,6-dimethyl-4-heptanoneC9H18O(9.5)16.4ketone
1,3-dioxolan-2-oneC3H4O3(29.5)16.4ester
phenylphosphonic difluorideC6H5F2OP16.4
ethyl 2-methylpropanoateC6H12O216.4ester
methyl acetateC3H6O210.716.5ester
N,N-dimethyltrifluoroacetamideC4H6F3NO16.6
2,2,2-trifluoro-N,N-dimethylacetamide     ⋮16.6amide; fluoro
butanenitrileC4H7N(19.2)16.6nitrile
ethyl butanoateC6H12O216.8ester
2-propanoneC3H6O12.517.0ketone
3,3-dimethyl-2-butanoneC6H12O(11.4)17.0ketone
dimethylcyanamideC3H6N2(20.5)17.0
ethyl formateC3H6O2(15.0)17.0ester
3-methyl-2-butanoneC5H10O(15.0)17.1ketone
ethyl acetateC4H8O29.317.1ester
ethyl propanoateC5H10O217.1ester
dimethyl carbonateC3H6O3(11.1)17.2ester
N,N-dimethylcarbamoyl chlorideC3H6ClNO17.2
2-butanoneC4H8O(15.8)17.4ketone
2-pentanoneC5H10O(15.4)17.5ketone