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
methyl 2,2-dimethylpropanoateC6H12O212.8ester;
methyl acetateC3H6O210.716.5ester;
methyl benzoateC8H8O2(9.7)15.0aromatic; ester;
methyl propanoateC4H8O2(9.5)11.0ester;
methyl propyl etherC4H10O18.1ether;
methyl trifluoroacetateC3H3F3O22.7ester; halo;
morpholineC4H9NO17.5ether; amine;
N,N,1,3-tetramethyl-1,3,2-diazaphospholidin-2-amine 2-oxideC6H16N3OP42.1
N,N,N',N'-tetramethylureaC5H12N2O9.231.0amide;
N,N-diethylacetamideC6H13NO13.632.2amide;
N,N-diethylformamideC5H11NO(16.7)30.9amide;
N,N-dimethylacetamideC4H9NO13.627.8amide;
N,N-dimethylanilineC8H11N(6.7)27.0amine; aromatic;
N,N-dimethylbenzylamineC9H13N21.0amine; aromatic;
N,N-dimethylcarbamoyl chlorideC3H6ClNO17.2
N,N-dimethylformamideC3H7NO16.026.6amide;
N,N-dimethylthioformamideC3H7NS18.8
N,N-dimethyltrifluoroacetamideC4H6F3NO16.6
N,N-dimethylurethaneC5H11NO222.4amide; ester;
N,N-dioctyloctan-1-amine oxideC24H51NO52.3
N-(azetidin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC7H18N3OP41.1
N-(aziridin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC6H16N3OP48.6
N-(dimethylamino-ethoxyphosphoryl)-N-methylmethanamineC6H17N2O2P36.4
N-(dimethylamino-pyrrolidin-1-ylphosphoryl)-N-methylmethanamineC8H20N3OP38.0
N-bis(dimethylamino)phosphoryl-N-ethylethanamineC8H22N3OP37.8