Periodic Table |
Lewis Acid/Base Interaction Matrix Database
Type 3 Lewis Acid/Base Complexation Chemistry |
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Common Brønsted Acids | |
Bonding: | The point-charge of the proton, H+, is able to efficiently penetrate and complex with the directional lobe shaped sp3/sp2/sp orbitals of all Lobe-HOMO Lewis bases. The resulting complexes are either covalent or polar-covalent. |
Charge: | Complexes may be negatively charged, positively charged or they may be neutral. |
Chemistry: | The vast majority of Brønsted acids are Type 3 Proton/Lobe-HOMO Lewis acid/base complexes, including all of the common mineral acids H2SO4, HCl, HNO3, H3PO4 etc. |
Congeneric Series: | Complexes show regular Brønsted acid behavior across congeneric series, ie across and down the periodic table: Brønsted acidity correlates with Lewis base to proton bond length, elsewhere in this webbook, here. CH4, methane and NH3, ammonia are the weakest Brønsted acids and have the shortest bond lengths while HI, hydrogen iodide and protonated xenon, [HXe]+, are the most acidic and have the longest bond lengths.Brønsted acidity increases with increasing conjugation and resulting π-stabilisation. Read more elsewhere in this webbook, here. |
Type 3 Lewis acid/base complex (generic) |
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Acetic acid more here |
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Acetone more here |
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Acetonitrile more here |
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Acetonitrile, protonated more here |
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Acetylene more here |
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Acrylic acid more here |
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Alcohol (generic) more here |
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1° Alcohol (generic) more here |
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3° Alcohol (generic) more here |
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Aldehyde, protonated (generic) more here |
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Alkene, monosubstituted (generic) more here |
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Alkene, tetrasubstituted (generic) more here |
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Alkyl alkoxy hydroxy carbenium ion (generic) more here |
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1° Alkyl oxonium ion (generic) more here |
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Alkyl telluronium ion (generic) more here |
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Alkyl, -CH2- (generic) more here |
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Allyl alcohol more here |
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1° Amide (generic) more here |
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Amide, protonated (generic) more here |
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2° Amine (generic) more here |
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Ammonia more here |
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Ammonium ion more here |
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1° Ammonium ion (generic) more here |
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2° Ammonium ion (generic) more here |
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3° Ammonium ion (generic) more here |
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Aniline more here |
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Argonium ion more here |
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Arsenate (dihydrogen) ion more here |
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Arsenate (hydrogen) ion more here |
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ortho Arsenic acid more here |
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Arsine more here |
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Arsonium ion more here |
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Arsonium ion (generic) more here |
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Benzenesulfonic acid more here |
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Benzoic acid more here |
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Benzylphenylsulfone more here |
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Bicarbonate ion more here |
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Bisulfite ion more here |
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Brønsted acid, stabilised carbanion (generic) more here |
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Bromoacetic acid more here |
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Bromonium ion more here |
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Bromonium ion, alkyl (generic) more here |
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Butane more here |
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Butanoic acid more here |
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tertiary Butanol more here |
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1-Butylammonium ion more here |
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tertiary Butyl oxonium ion more here |
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Carbenium ion more here |
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Carbonic acid more here |
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Carboxylic acid (generic) more here |
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Carboxylic acid, protonated (generic) more here |
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Chloroacetic acid more here |
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Chloronium ion more here |
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Chloronium ion, alkyl (generic) more here |
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meta Chloroperoxybenzoic acid more here |
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Chlorous acid more here |
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cis Cinnamic acid more here |
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trans Cinnamic acid more here |
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Citrate (dihydrogen) ion more here |
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Citric acid more here |
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Cyanoacetic acid more here |
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Cyclobutane more here |
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Cycloheptatriene more here |
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Cyclohexane more here |
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Cyclohexanone more here |
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Cyclopentane more here |
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Cyclopentane carboxylic acid more here |
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Cyclopropane more here |
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Cyclopropane carboxylic acid more here |
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Deuterium oxide more here |
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Dialkyl arsine (generic) more here |
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Dialkyl oxonium ion (generic) more here |
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Dialkyl telluronium ion (generic) more here |
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Dialkylhydroxy carbenium ion (generic) more here |
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Dichloroacetic acid more here |
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Diethyloxonium ion more here |
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Diethylsulfonium ion more here |
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Dihydrogen disulfide more here |
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Dihydrogen phosphate ion more here |
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Dihydroxymethyl carbenium ion more here |
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Diisopropylamine more here |
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beta-Diketone (generic) more here |
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Dimethyl sulfonium ion more here |
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Dimethylamine more here |
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Dimethylammonium ion more here |
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Dimethylformamide, protonated more here |
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Dimethylhydroxy carbenium ion more here |
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Dimethyloxonium ion more here |
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Dimethylsulfoxide more here |
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Dimethylsulfoxide, protonated more here |
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Dinitromethane more here |
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2,4-Dinitrophenol more here |
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1,4-Dioxane, protonated more here |
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Diphenyl phosphine more here |
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Diphenylamine more here |
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Diphenylammonium ion more here |
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Disulfide (hydrogen) ion more here |
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1,2-Dithioethane more here |
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1,2-Dithioethane monoanion more here |
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Ethane more here |
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Ethane thiol more here |
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Ethanol more here |
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Ethanolamine, protonated more here |
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Ethyl acetate more here |
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Ethylacetate, protonated more here |
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Ethylamine more here |
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Ethylammonium ion more here |
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Ethylene more here |
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Ethylene glycol more here |
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Ethylene glycol anion more here |
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Ethylenediamine tetraacetic acid more here |
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Ethylenediamine, mono-protonated more here |
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Ethylenediaminetetraacetic acid dianion more here |
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Ethylenediaminetetraacetic acid mono anion more here |
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Ethylenediaminetetraacetic acid trianion more here |
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Ethylium ion more here |
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Ethyloxonium ion more here |
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Ethylsulfonium ion more here |
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Fluorene more here |
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Fluoronium ion more here |
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Fluoronium ion, alkyl (generic) more here |
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Fluorosulfonic acid more here |
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Formic acid more here |
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Fumarate (hydrogen) ion more here |
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Fumaric acid more here |
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Germanate (trihydrogen) ion more here |
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Germane more here |
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Germane (generic) more here |
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Germanic acid more here |
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Glycolic acid more here |
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Guanidine, protonated more here |
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Hydrazine more here |
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Hydrazoic acid more here |
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Hydrogen bromide more here |
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Hydrogen chloride more here |
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Hydrogen citrate ion more here |
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Hydrogen cyanide more here |
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Hydrogen deuterium oxide more here |
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Hydrogen fluoride more here |
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Hydrogen iodide more here |
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Hydrogen peroxide more here |
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Hydrogen phosphite ion more here |
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Hydrogen selenide more here |
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Hydrogen sulfate ion more here |
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Hydrogen sulfide more here |
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Hydrogen sulfide anion more here |
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Hydrogen telluride more here |
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Hydroxy carbenium ion more here |
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Hydroxyammonium ion more here |
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Hydroxydialkoxy carbenium ion (generic) more here |
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Hydroxymethyl carbenium ion more here |
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Hypobromous acid more here |
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Hypochlorous acid more here |
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Hypofluouous acid more here |
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Hypoiodous acid more here |
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Hypophosphorous acid more here |
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Imidazole more here |
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Imidazonium ion more here |
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Imine, dialkyl (generic) more here |
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Iodic acid more here |
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Iodoacetic acid more here |
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Iodonium ion more here |
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Iodonium ion, alkyl (generic) more here |
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Isocyanic acid more here |
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Isopropyl oxonium ion more here |
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beta-Ketoaldehyde (generic) more here |
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beta-Ketoester (generic) more here |
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Kryptonium ion more here |
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(+/-) Lactic acid more here |
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Maleic acid more here |
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Maleic acid monoanion more here |
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Malonate (hydrogen) ion more here |
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Malonate diester (generic) more here |
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Malonic acid more here |
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Malononitrile more here |
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(+/-) Mandelic acid more here |
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Methane more here |
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Methane thiol more here |
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Methanol more here |
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Methoxyacetic acid more here |
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4-Methyl-2,6-di-tert-butyl pryidinium ion more here |
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Methyl ketone (generic) more here |
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Methylamine more here |
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Methylammonium ion more here |
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Methyloxonium ion more here |
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2-Methylpropane more here |
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2-Methylpyridinium ion more here |
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Methylsulfonium ion more here |
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Methylsulfonyl acetic acid more here |
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Methylthioacetic acid more here |
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Neonium ion more here |
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Nitric acid, concentrated more here |
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Nitric acid, fuming more here |
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Nitric acid, gas phase species more here |
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Nitrile (generic) more here |
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Nitrilium ion (generic) more here |
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Nitro compound (generic) more here |
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Nitroacetic acid more here |
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Nitrobenzene, protonated more here |
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Nitromethane, protonated more here |
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3-Nitrophenol more here |
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4-Nitrophenol more here |
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4-Nitrophenylammonium ion more here |
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Nitrosyl hydrogen sulfate more here |
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Nitrous acid more here |
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Tetrahydroorthoperiodate ion more here |
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Orthoperiodic acid more here |
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Oxalate monoanion more here |
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Oxalic acid more here |
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Oxonium ion more here |
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2,4-Pentanedione more here |
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Peracetic acid more here |
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Perchloric acid more here |
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Peroxide, organic (generic) more here |
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Peroxodisulfate(VI) ion more here |
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Peroxodisulfuric acid more here |
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Phenol more here |
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Phenyl arsine more here |
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Phenyl silane more here |
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Phenyl telluride more here |
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Phenylacetylene more here |
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Phenylammonium ion more here |
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Phenyloxonium ion more here |
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Phosphate dianion, hydrogen more here |
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Phosphine more here |
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Phosphonate, diethyl 1° alkyl (generic) more here |
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Phosphonium ion more here |
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Phosphonium ion (generic) more here |
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Phosphoric acid more here |
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Phosphorus acid more here |
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Phthalate (o) (hydrogen) ion more here |
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o-Phthalic acid more here |
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Phthalimide more here |
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Picric acid more here |
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Piperidine, protonated more here |
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Propane more here |
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Propanoic acid more here |
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2-Propanol more here |
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Propargyl alcohol more here |
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1-Propyl ammonium ion more here |
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Pyridinium ion more here |
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Pyrrolidine, protonated more here |
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Pyruvic acid more here |
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Salicyate ion more here |
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Salicylic acid more here |
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Selenite (hydrogen) ion more here |
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Selenonium ion more here |
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Selenous acid more here |
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Selinophenol more here |
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Silane more here |
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Silane (generic) more here |
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Sodium hydrogen sulfite more here |
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Stibine more here |
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Stibonium ion more here |
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(-) Strychnine, protonated more here |
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Succinate (hydrogen) ion more here |
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Succinic acid more here |
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Succinimide more here |
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Sulfamic acid more here |
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Sulfinic acid (generic) more here |
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Sulfonium ion more here |
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Sulfonium ion, alkyl (generic) more here |
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Sulfonium ion, dialkyl (generic) more here |
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Sulfuric acid more here |
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Sulfurous acid more here |
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d/l-Tartaric acid more here |
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Tartrate (hydrogen) ion more here |
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Telluride (generic) more here |
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Tellurite (hydrogen) ion more here |
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Telluronium ion more here |
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Tellurous acid more here |
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Tetrahydrofuran, protonated more here |
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Thiocarbenium ion (generic) more here |
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Thiocyanic acid more here |
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Thiol (generic) more here |
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Thiophenol more here |
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p-Toluenesulfonic acid monohydrate more here |
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Trichloroacetic acid more here |
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2,2,2-Trichloroethanol more here |
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Tricyanomethane more here |
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Triethylammonium ion more here |
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Triethylarsonium ion more here |
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Triethylphosphonium ion more here |
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Trifluoroacetic acid more here |
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2,2,2-Trifluoroethanol more here |
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Trifluoromethanesulfonic acid more here |
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Trimethylammonium ion more here |
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4-(Trimethylammonium) phenol more here |
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Trimethylphosphonium ion more here |
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2,4,6-Trimethylpyridinium ion more here |
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bis(Trimethylsilyl) amine more here |
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Trimethylsulfoxonium ion more here |
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Trimethylsulfoxonium ylid more here |
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Triphenylmethane more here |
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Urea, protonated more here |
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Water more here |