Periodic Table |
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Lewis Acid/Base Interaction Matrix Database
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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 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 |