Gutmann Acceptor and Donor number

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