Gutmann Acceptor and Donor number

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 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

See →
Lewis donor strength for scales of Lewis bases.

NameFormulaANDN
1,1,1,3,3,3-hexafluoro-2-propanolC3H2F6O66.7-
1,1-dichloroethaneC2H4Cl216.2-
1,2,3-propanetriolC3H8O3-19.0
1,2-diaminoethaneC2H8N220.955.0
1,2-dichlorobenzeneC6H4Cl2-3.0
1,2-dichloroethaneC2H4Cl216.70.0
1,2-dimethoxyethaneC4H10O210.220.0
1,3,2-dioxathiolan-2-oxideC2H4O3S-15.3
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octaneC10H18O-24.0
1,3,5-trimethylbenzeneC9H12-10.0
1,3-dichlorobenzeneC6H4Cl2-2.0
1,3-dimethyl-2-imidazolidinoneC5H10N2O-27.7
1,3-dimethylbenzeneC8H10-5.0
1,3-dimethyltetrahydropyrimidin-2(1H)-oneC6H12N2O-33.0
1,3-dimethylureaC3H8N2O-29.7
1,3-dioxolan-2-oneC3H4O3-16.4
1,3-dioxolaneC3H6O2-21.2
1,4-dimethylbenzeneC8H10-5.0
1-di(piperidin-1-yl)phosphorylpiperidineC15H30N3OP-40.9
1-methylazepan-2-oneC7H13NO-27.1
2,2,2-trifluoro-N,N-dimethylacetamideC4H6F3NO-16.6
2,2,2-trifluoroethanolC2H3F3O53.8-
2,2,4,4-tetramethyl-3-pentanoneC9H18O-10.3
2,2,4-trimethylpentan-3-oneC8H16O-11.3
2,2,5,5-tetramethylhexan-3-oneC10H20O-11.8
2,2,6,6-tetramethyl-4-heptanoneC11H22O-15.0
2,2-dimethylpentan-3-oneC7H14O-14.6
2,3-butanedioneC4H6O2-11.0
2,4-dimethyl-3-pentanoneC7H14O-16.2
2,6-dimethyl-4-heptanoneC9H18O-16.4
2-aminoethanolC2H7NO33.7-
2-butanoneC4H8O-17.4
2-chloroanilineC6H6ClN-31.0
2-chloroethanolC2H5ClO-5.0
2-methyl-1-propanolC4H10O-37.0
2-methyl-2-butanolC5H12O-44.0
2-methyl-2-propanamineC4H11N-57.0
2-methyl-2-propanolC4H10O27.138.0
2-methylpentan-3-oneC6H12O-16.2
2-methylpropanenitrileC4H7N-15.4
2-methyltetrahydrofuranC5H10O-12.0
2-pentanoneC5H10O-17.5
2-phenylacetonitrileC8H7N-15.1
2-phenylethanolC8H10O33.823.0
2-propanolC3H8O33.521.1
2-propanoneC3H6O12.517.0
3,3-dimethyl-2-butanoneC6H12O-17.0
3-methyl-1-butanolC5H12O-32.0
3-methyl-2-butanoneC5H10O-17.1
3-methylphenolC7H8O50.4-
3-methylpyridineC6H7N-39.0
3-pentanoneC5H10O-15.0
4,4,5,5-tetrachloro-1,3-dioxolan-2-oneC3Cl4O3-0.8
4,5-dichloro-1,3-dioxolan-2-oneC3H2Cl2O316.73.2
4-methyl-2-oxo-1,3-dioxolaneC4H6O318.315.1
4-methyl-2-pentanoneC6H12O-16.0
4-methylpyridineC6H7N-34.0
4-methylpyridine N-oxideC6H7NO-36.3
acetic acidC2H4O252.920.0
acetic anhydrideC4H6O3-10.5
acetonitrileC2H3N18.914.1
acetophenoneC8H8O-15.0
acetyl chlorideC2H3ClO-0.7
ammoniaH3N-59.0
anilineC6H7N-35.0
antimony pentachlorideCl5Sb100.0-
benzaldehydeC7H6O-16.0
benzeneC6H68.20.1
benzonitrileC7H5N15.511.9
benzophenoneC13H10O-16.0
benzoyl chlorideC7H5ClO-2.3
benzoyl fluorideC7H5FO-2.0
benzyl alcoholC7H8O36.823.0
bis(2-chloroethyl) etherC4H8Cl2O-16.0
bis(2-methoxyethyl) etherC6H14O39.9-
bis(diethylamino)-pyrrolidinophosphine oxideC12H28N3OP-40.2
bis(dimethylamino)-(ethylamino)phosphine oxideC6H18N3OP-41.2
bis(ethylamino)-(dimethylamino)phosphine oxideC6H18N3OP-40.6
bis(pyrrolidino)diethylaminophosphine oxideC12H26N3OP-55.2
bromobenzeneC6H5Br-3.0
butanenitrileC4H7N-16.6
butanolC4H10O36.819.5
butyl acetateC6H12O2-15.0
butylamineC4H11N-42.0
carbon disulfideCS2-2.0
chloroacetonitrileC2H2ClN-10.0
chlorobenzeneC6H5Cl-3.3
cumeneC9H12-6.0
cyclohexaneC6H12-0.0
cyclohexanolC6H12O-25.0
cyclohexanoneC6H10O-18.0
cyclopentanoneC5H8O-18.0
decanolC10H22O-31.0
dibenzyl etherC14H14O-19.0
dibutyl etherC8H18O-19.0
dibutyl sulfoxideC8H18OS-31.0
dichloromethaneCH2Cl220.41.0
diethyl carbonateC5H10O3-16.0
diethyl dimethylamidophosphateC6H16NO3P-29.5
diethyl dimethylphosphoramidateC6H16NO3P-29.5
diethyl etherC4H10O3.919.2
diethyl sulfideC4H10S-41.0
diethylamineC4H11N9.450.0
diisopropyl etherC6H14O-19.0
dimethyl carbonateC3H6O3-17.2
dimethyl sulfideC2H6S-40.0
dimethyl sulfoxideC2H6OS19.329.8
dimethylamino-di(azetidin-1-yl)phosphine oxideC8H18N3OP-42.3
dimethylcyanamideC3H6N2-17.0
dioctyl methylphosphonateC17H37O3P-31.2
dioctyl sulfoxideC16H34OS-30.3
dioxaneC4H8O210.314.3
diphenylphosphinic chlorideC12H10ClOP-22.4
dipropyl etherC6H14O-18.0
ethanediolC2H6O2-20.0
ethanolC2H6O37.919.2
ethoxybenzeneC8H10O-8.0
ethyl 2,2-dimethylpropanoateC7H14O2-13.0
ethyl 2-methylpropanoateC6H12O2-16.4
ethyl acetateC4H8O29.317.1
ethyl benzoateC9H10O2-15.0
ethyl butanoateC6H12O2-16.8
ethyl chloroacetateC4H7ClO2-13.0
ethyl chloroformateC3H5ClO2-21.3
ethyl dichloroacetateC4H6Cl2O2-9.4
ethyl formateC3H6O2-17.0
ethyl propanoateC5H10O2-17.1
ethyl trichloroacetateC4H5Cl3O2-3.1
ethylamineC2H7N-55.0
ethylamino-dipyrrolidinophosphine oxideC10H22N3OP-42.6
ethylbenzeneC8H10-6.0
fluorobenzeneC6H5F-3.0
formamideCH3NO39.824.0
formic acidCH2O283.619.0
furanC4H4O-6.0
heptaneC7H160.00.0
hexaethylphosphoramideC12H30N3OP-36.6
hexamethylphosphoramideC6H18N3OP10.638.8
hexaneC6H140.00.0
hexanolC6H14O-30.0
hydrazineH4N2-44.0
iodobenzeneC6H5I-4.0
isopropyl 2,2-dimethylpropanoateC8H16O2-13.5
isopropyl acetateC5H10O2-17.5
isopropyl pivalateC8H16O2-13.5
methanesulfonic acidCH4O3S126.3-
methanolCH4O41.519.0
methoxybenzeneC7H8O-9.0
methyl 2,2-dimethylpropanoateC6H12O2-12.8
methyl acetateC3H6O210.716.5
methyl benzoateC8H8O2-15.0
methyl propanoateC4H8O2-11.0
methyl propyl etherC4H10O-18.1
methyl trifluoroethanoateC3H3F3O2-2.7
morpholineC4H9NO17.5-
N,N,1,3-tetramethyl-1,3,2-diazaphospholidin-2-amine 2-oxideC6H16N3OP-42.1
N,N,N',N'-tetramethylureaC5H12N2O9.231.0
N,N-diethylacetamideC6H13NO13.632.2
N,N-diethylformamideC5H11NO-30.9
N,N-dimethylacetamideC4H9NO13.627.8
N,N-dimethylanilineC8H11N-27.0
N,N-dimethylbenzylamineC9H13N-21.0
N,N-dimethylcarbamoyl chlorideC3H6ClNO-17.2
N,N-dimethylformamideC3H7NO16.026.6
N,N-dimethylthioformamideC3H7NS18.8-
N,N-dimethyltrifluoroacetamideC4H6F3NO-16.6
N,N-dimethylurethaneC5H11NO2-22.4
N,N-dioctyloctan-1-amine oxideC24H51NO-52.3
N-(azetidin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC7H18N3OP-41.1
N-(aziridin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC6H16N3OP-48.6
N-(dimethylamino-ethoxyphosphoryl)-N-methylmethanamineC6H17N2O2P-36.4
N-(dimethylamino-pyrrolidin-1-ylphosphoryl)-N-methylmethanamineC8H20N3OP-38.0
N-bis(dimethylamino)phosphoryl-N-ethylethanamineC8H22N3OP-37.8
N-bis(ethylamino)phosphorylethanamineC6H18N3OP-47.3
N-dipyrrolidin-1-ylphosphoryl-N-methylmethanamineC10H22N3OP-45.4
N-methylanilineC7H9N-33.0
N-methylformamideC2H5NO32.127.0
N-methylpyrrolidoneC5H9NO13.327.3
N-[bis(aziridin-1-yl)phosphoryl]-N-methylmethanamineC6H14N3OP-49.1
nitrobenzeneC6H5NO214.84.4
nitroethaneC2H5NO2-5.0
nitromethaneCH3NO220.52.7
octanolC8H18O-32.0
oxaneC5H10O-22.0
oxolan-2-oneC4H6O217.318.0
pentanolC5H12O-25.0
phenolC6H6O-11.0
phenylphosphonic dichlorideC6H5Cl2OP-18.5
phenylphosphonic difluorideC6H5F2OP-16.4
phosphorus oxychlorideCl3OP-11.7
piperidineC5H11N-40.0
propanenitrileC3H5N-16.1
propanolC3H8O37.319.8
propanoyl chlorideC3H5ClO-3.2
propyl acetateC5H10O2-16.0
pyridineC5H5N14.233.1
pyridine N-oxideC5H5NO-34.4
pyridinium dichromateC10H12Cr2N2O718.3-
quinolineC9H7N-32.0
selenium oxychlorideH2Cl2OSe-12.2
styreneC8H8-5.0
sulfolaneC4H8O2S19.214.8
sulfuryl chlorideCl2O2S-0.1
tert-butyl acetateC6H12O2-35.9
tetrachloromethaneCCl48.60.0
tetrahydrofuranC4H8O8.020.0
thionyl chlorideCl2OS-0.4
tolueneC7H8-0.1
tri(azetidin-1-yl)phosphine oxideC9H18N3OP-43.0
tributyl phosphateC12H27O4P9.923.7
tributylamineC12H27N-50.0
trichloromethaneCHCl323.14.0
triethyl phosphateC6H15O4P-26.0
triethylamineC6H15N1.461.0
triethylenephosphoramideC6H12N3OP-50.0
trifluoroacetic acidC2HF3O2105.3-
trifluoromethanesulfonic acidCHF3O3S129.1-
trimethyl phosphateC3H9O4P16.323.0
trimethylureaC4H10N2O-29.3
trioctylphosphine oxideC24H51OP-33.8
tripyrrolidinophosphine oxideC12H24N3OP-47.2
waterH2O54.818.0