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 → 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

See →
Lewis donor strength for scales of Lewis bases.

NameFormulaANDN
cyclohexaneC6H12-0.0
sulfuryl chlorideCl2O2S-0.1
tolueneC7H8-0.1
thionyl chlorideCl2OS-0.4
acetyl chlorideC2H3ClO-0.7
4,4,5,5-tetrachloro-1,3-dioxolan-2-oneC3Cl4O3-0.8
benzoyl fluorideC7H5FO-2.0
carbon disulfideCS2-2.0
1,3-dichlorobenzeneC6H4Cl2-2.0
benzoyl chlorideC7H5ClO-2.3
methyl trifluoroacetateC3H3F3O2-2.7
1,2-dichlorobenzeneC6H4Cl2-3.0
fluorobenzeneC6H5F-3.0
bromobenzeneC6H5Br-3.0
ethyl trichloroacetateC4H5Cl3O2-3.1
propanoyl chlorideC3H5ClO-3.2
chlorobenzeneC6H5Cl-3.3
iodobenzeneC6H5I-4.0
styreneC8H8-5.0
1,3-dimethylbenzeneC8H10-5.0
nitroethaneC2H5NO2-5.0
1,4-dimethylbenzeneC8H10-5.0
2-chloroethanolC2H5ClO-5.0
ethylbenzeneC8H10-6.0
cumeneC9H12-6.0
furanC4H4O-6.0
ethoxybenzeneC8H10O-8.0
methoxybenzeneC7H8O-9.0
ethyl dichloroacetateC4H6Cl2O2-9.4
1,3,5-trimethylbenzeneC9H12-10.0
chloroacetonitrileC2H2ClN-10.0
2,2,4,4-tetramethyl-3-pentanoneC9H18O-10.3
acetic anhydrideC4H6O3-10.5
phenolC6H6O-11.0
methyl propanoateC4H8O2-11.0
2,3-butanedioneC4H6O2-11.0
2,2,4-trimethylpentan-3-oneC8H16O-11.3
phosphorus oxychlorideCl3OP-11.7
2,2,5,5-tetramethylhexan-3-oneC10H20O-11.8
2-methyltetrahydrofuranC5H10O-12.0
selenium oxychlorideH2Cl2OSe-12.2
methyl 2,2-dimethylpropanoateC6H12O2-12.8
ethyl chloroacetateC4H7ClO2-13.0
ethyl 2,2-dimethylpropanoateC7H14O2-13.0
isopropyl pivalateC8H16O2-13.5
isopropyl 2,2-dimethylpropanoateC8H16O2-13.5
2,2-dimethylpentan-3-oneC7H14O-14.6
3-pentanoneC5H10O-15.0
2,2,6,6-tetramethyl-4-heptanoneC11H22O-15.0
acetophenoneC8H8O-15.0
methyl benzoateC8H8O2-15.0
butyl acetateC6H12O2-15.0
ethyl benzoateC9H10O2-15.0
2-phenylacetonitrileC8H7N-15.1
1,3,2-dioxathiolan-2-oxideC2H4O3S-15.3
2-methylpropanenitrileC4H7N-15.4
benzophenoneC13H10O-16.0
diethyl carbonateC5H10O3-16.0
benzaldehydeC7H6O-16.0
bis(2-chloroethyl) etherC4H8Cl2O-16.0
propyl acetateC5H10O2-16.0
4-methyl-2-pentanoneC6H12O-16.0
propanenitrileC3H5N-16.1
2-methylpentan-3-oneC6H12O-16.2
2,4-dimethyl-3-pentanoneC7H14O-16.2
2,6-dimethyl-4-heptanoneC9H18O-16.4
1,3-dioxolan-2-oneC3H4O3-16.4
phenylphosphonic difluorideC6H5F2OP-16.4
ethyl 2-methylpropanoateC6H12O2-16.4
N,N-dimethyltrifluoroacetamideC4H6F3NO-16.6
butanenitrileC4H7N-16.6
2,2,2-trifluoro-N,N-dimethylacetamideC4H6F3NO-16.6
ethyl butanoateC6H12O2-16.8
3,3-dimethyl-2-butanoneC6H12O-17.0
ethyl formateC3H6O2-17.0
dimethylcyanamideC3H6N2-17.0
ethyl propanoateC5H10O2-17.1
3-methyl-2-butanoneC5H10O-17.1
dimethyl carbonateC3H6O3-17.2
N,N-dimethylcarbamoyl chlorideC3H6ClNO-17.2
2-butanoneC4H8O-17.4
2-pentanoneC5H10O-17.5
isopropyl acetateC5H10O2-17.5
dipropyl etherC6H14O-18.0
cyclohexanoneC6H10O-18.0
cyclopentanoneC5H8O-18.0
methyl propyl etherC4H10O-18.1
phenylphosphonic dichlorideC6H5Cl2OP-18.5
dibenzyl etherC14H14O-19.0
1,2,3-propanetriolC3H8O3-19.0
diisopropyl etherC6H14O-19.0
dibutyl etherC8H18O-19.0
ethanediolC2H6O2-20.0
N,N-dimethylbenzylamineC9H13N-21.0
1,3-dioxolaneC3H6O2-21.2
ethyl chloroformateC3H5ClO2-21.3
oxaneC5H10O-22.0
N,N-dimethylurethaneC5H11NO2-22.4
diphenylphosphinic chlorideC12H10ClOP-22.4
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octaneC10H18O-24.0
pentanolC5H12O-25.0
cyclohexanolC6H12O-25.0
triethyl phosphateC6H15O4P-26.0
N,N-dimethylanilineC8H11N-27.0
1-methylazepan-2-oneC7H13NO-27.1
1,3-dimethyl-2-imidazolidinoneC5H10N2O-27.7
trimethylureaC4H10N2O-29.3
diethyl dimethylphosphoramidateC6H16NO3P-29.5
diethyl dimethylamidophosphateC6H16NO3P-29.5
1,3-dimethylureaC3H8N2O-29.7
hexanolC6H14O-30.0
dioctyl sulfoxideC16H34OS-30.3
N,N-diethylformamideC5H11NO-30.9
dibutyl sulfoxideC8H18OS-31.0
2-chloroanilineC6H6ClN-31.0
decanolC10H22O-31.0
dioctyl methylphosphonateC17H37O3P-31.2
octanolC8H18O-32.0
quinolineC9H7N-32.0
3-methyl-1-butanolC5H12O-32.0
1,3-dimethyltetrahydropyrimidin-2(1H)-oneC6H12N2O-33.0
N-methylanilineC7H9N-33.0
trioctylphosphine oxideC24H51OP-33.8
4-methylpyridineC6H7N-34.0
pyridine N-oxideC5H5NO-34.4
anilineC6H7N-35.0
tert-butyl acetateC6H12O2-35.9
4-methylpyridine N-oxideC6H7NO-36.3
N-(dimethylamino-ethoxyphosphoryl)-N-methylmethanamineC6H17N2O2P-36.4
hexaethylphosphoramideC12H30N3OP-36.6
2-methyl-1-propanolC4H10O-37.0
N-bis(dimethylamino)phosphoryl-N-ethylethanamineC8H22N3OP-37.8
N-(dimethylamino-pyrrolidin-1-ylphosphoryl)-N-methylmethanamineC8H20N3OP-38.0
3-methylpyridineC6H7N-39.0
dimethyl sulfideC2H6S-40.0
piperidineC5H11N-40.0
bis(diethylamino)-pyrrolidinophosphine oxideC12H28N3OP-40.2
bis(ethylamino)-(dimethylamino)phosphine oxideC6H18N3OP-40.6
1-di(piperidin-1-yl)phosphorylpiperidineC15H30N3OP-40.9
diethyl sulfideC4H10S-41.0
N-(azetidin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC7H18N3OP-41.1
bis(dimethylamino)-(ethylamino)phosphine oxideC6H18N3OP-41.2
butylamineC4H11N-42.0
N,N,1,3-tetramethyl-1,3,2-diazaphospholidin-2-amine 2-oxideC6H16N3OP-42.1
dimethylamino-di(azetidin-1-yl)phosphine oxideC8H18N3OP-42.3
ethylamino-dipyrrolidinophosphine oxideC10H22N3OP-42.6
tri(azetidin-1-yl)phosphine oxideC9H18N3OP-43.0
2-methyl-2-butanolC5H12O-44.0
hydrazineH4N2-44.0
N-dipyrrolidin-1-ylphosphoryl-N-methylmethanamineC10H22N3OP-45.4
tripyrrolidinophosphine oxideC12H24N3OP-47.2
N-bis(ethylamino)phosphorylethanamineC6H18N3OP-47.3
N-(aziridin-1-yl-dimethylaminophosphoryl)-N-methylmethanamineC6H16N3OP-48.6
N-[bis(aziridin-1-yl)phosphoryl]-N-methylmethanamineC6H14N3OP-49.1
tributylamineC12H27N-50.0
triethylenephosphoramideC6H12N3OP-50.0
N,N-dioctyloctan-1-amine oxideC24H51NO-52.3
ethylamineC2H7N-55.0
bis(pyrrolidino)diethylaminophosphine oxideC12H26N3OP-55.2
2-methyl-2-propanamineC4H11N-57.0
ammoniaH3N-59.0
hexaneC6H140.00.0
heptaneC7H160.00.0
triethylamineC6H15N1.461.0
diethyl etherC4H10O3.919.2
tetrahydrofuranC4H8O8.020.0
benzeneC6H68.20.1
tetrachloromethaneCCl48.60.0
N,N,N',N'-tetramethylureaC5H12N2O9.231.0
ethyl acetateC4H8O29.317.1
diethylamineC4H11N9.450.0
bis(2-methoxyethyl) etherC6H14O39.9-
tributyl phosphateC12H27O4P9.923.7
1,2-dimethoxyethaneC4H10O210.220.0
dioxaneC4H8O210.314.3
hexamethylphosphoramideC6H18N3OP10.638.8
methyl acetateC3H6O210.716.5
2-propanoneC3H6O12.517.0
N-methylpyrrolidoneC5H9NO13.327.3
N,N-dimethylacetamideC4H9NO13.627.8
N,N-diethylacetamideC6H13NO13.632.2
pyridineC5H5N14.233.1
nitrobenzeneC6H5NO214.84.4
benzonitrileC7H5N15.511.9
N,N-dimethylformamideC3H7NO16.026.6
1,1-dichloroethaneC2H4Cl216.2-
trimethyl phosphateC3H9O4P16.323.0
1,2-dichloroethaneC2H4Cl216.70.0
4,5-dichloro-1,3-dioxolan-2-oneC3H2Cl2O316.73.2
oxolan-2-oneC4H6O217.318.0
morpholineC4H9NO17.5-
1-methylpyrrolidin-2-thioneC5H9NS17.7-
pyridinium dichromateC10H12Cr2N2O718.3-
4-methyl-2-oxo-1,3-dioxolaneC4H6O318.315.1
N,N-dimethylthioformamideC3H7NS18.8-
acetonitrileC2H3N18.914.1
sulfolaneC4H8O2S19.214.8
dimethyl sulfoxideC2H6OS19.329.8
dichloromethaneCH2Cl220.41.0
nitromethaneCH3NO220.52.7
1,2-diaminoethaneC2H8N220.955.0
trichloromethaneCHCl323.14.0
2-methyl-2-propanolC4H10O27.138.0
N-methylformamideC2H5NO32.127.0
2-propanolC3H8O33.521.1
2-aminoethanolC2H7NO33.7-
2-phenylethanolC8H10O33.823.0
butanolC4H10O36.819.5
benzyl alcoholC7H8O36.823.0
propanolC3H8O37.319.8
ethanolC2H6O37.919.2
formamideCH3NO39.824.0
methanolCH4O41.519.0
3-methylphenolC7H8O50.4-
acetic acidC2H4O252.920.0
2,2,2-trifluoroethanolC2H3F3O53.8-
waterH2O54.818.0
1,1,1,3,3,3-hexafluoro-2-propanolC3H2F6O66.7-
formic acidCH2O283.619.0
antimony pentachlorideCl5Sb100.0-
trifluoroacetic acidC2HF3O2105.3-
methanesulfonic acidCH4O3S126.3-
trifluoromethanesulfonic acidCHF3O3S129.1-