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
N-bis(ethylamino)phosphorylethanamineC6H18N3OP47.3
N-dipyrrolidin-1-ylphosphoryl-N-methylmethanamineC10H22N3OP45.4
N-methylanilineC7H9N(18.0)33.0amine; aromatic
N-methylformamideC2H5NO32.127.0amide
N-methylpyrrolidoneC5H9NO13.327.3amide
N-[bis(aziridin-1-yl)phosphoryl]-N-methylmethanamineC6H14N3OP49.1
nitrobenzeneC6H5NO214.84.4nitro; aromatic
nitroethaneC2H5NO2(20.1)5.0nitro
nitromethaneCH3NO220.52.7nitro
octanolC8H18O(29.0)32.0alcohol
oxaneC5H10O(6.9)22.0ether
oxolan-2-oneC4H6O217.318.0ester
pentanolC5H12O(30.5)25.0alcohol
phenolC6H6O(38.6)11.0
phenylphosphonic dichlorideC6H5Cl2OP18.5
phenylphosphonic difluorideC6H5F2OP16.4
phosphorus oxychlorideCl3OP11.7
piperidineC5H11N(4.8)40.0amine
propanenitrileC3H5N(20.1)16.1nitrile
propanolC3H8O37.319.8alcohol
propanoyl chlorideC3H5ClO3.2
propyl acetateC5H10O2(8.6)16.0ester
pyridineC5H5N14.233.1heteroaromatic
pyridine N-oxideC5H5NO34.4heteroaromatic
pyridinium dichromateC10H12Cr2N2O718.3