Lewis Acid/Base Interaction Matrix Database


Type 3 Lewis Acid/Base Complexation Chemistry
Common Brønsted Acids

               H+   +   H3C     CH4
               H+   +   H2O:     [H3O]+

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)
Acetic acid

more here
Acetone

more here
Acetonitrile

more here
Acetonitrile, protonated

more here
Acetylene

more here
Acrylic acid

more here
Alcohol (generic)

more here
1° Alcohol (generic)

more here
3° Alcohol (generic)

more here
Aldehyde, protonated (generic)

more here
Alkene, monosubstituted (generic)

more here
Alkene, tetrasubstituted (generic)

more here
Alkyl alkoxy hydroxy carbenium ion (generic)

more here
1° Alkyl oxonium ion (generic)

more here
Alkyl telluronium ion (generic)

more here
Alkyl, -CH2- (generic)

more here
Allyl alcohol

more here
1° Amide (generic)

more here
Amide, protonated (generic)

more here
2° Amine (generic)

more here
Ammonia

more here
Ammonium ion

more here
1° Ammonium ion (generic)

more here
2° Ammonium ion (generic)

more here
3° Ammonium ion (generic)

more here
Aniline

more here
Argonium ion

more here
Arsenate (dihydrogen) ion

more here
Arsenate (hydrogen) ion

more here
ortho Arsenic acid

more here
Arsine

more here
Arsonium ion

more here
Arsonium ion (generic)

more here
Benzenesulfonic acid

more here
Benzoic acid

more here
Benzylphenylsulfone

more here
Bicarbonate ion

more here
Bisulfite ion

more here
Brønsted acid, stabilised carbanion (generic)

more here
Bromoacetic acid

more here
Bromonium ion

more here
Bromonium ion, alkyl (generic)

more here
Butane

more here
Butanoic acid

more here
tertiary Butanol

more here
1-Butylammonium ion

more here
tertiary Butyl oxonium ion

more here
Carbenium ion

more here
Carbonic acid

more here
Carboxylic acid (generic)

more here
Carboxylic acid, protonated (generic)

more here
Chloroacetic acid

more here
Chloronium ion

more here
Chloronium ion, alkyl (generic)

more here
meta Chloroperoxybenzoic acid

more here
Chlorous acid

more here
cis Cinnamic acid

more here
trans Cinnamic acid

more here
Citrate (dihydrogen) ion

more here
Citric acid

more here
Cyanoacetic acid

more here
Cyclobutane

more here
Cycloheptatriene

more here
Cyclohexane

more here
Cyclohexanone

more here
Cyclopentane

more here
Cyclopentane carboxylic acid

more here
Cyclopropane

more here
Cyclopropane carboxylic acid

more here
Deuterium oxide

more here
Dialkyl arsine (generic)

more here
Dialkyl oxonium ion (generic)

more here
Dialkyl telluronium ion (generic)

more here
Dialkylhydroxy carbenium ion (generic)

more here
Dichloroacetic acid

more here
Diethyloxonium ion

more here
Diethylsulfonium ion

more here
Dihydrogen disulfide

more here
Dihydrogen phosphate ion

more here
Dihydroxymethyl carbenium ion

more here
Diisopropylamine

more here
beta-Diketone (generic)

more here
Dimethyl sulfonium ion

more here
Dimethylamine

more here
Dimethylammonium ion

more here
Dimethylformamide, protonated

more here
Dimethylhydroxy carbenium ion

more here
Dimethyloxonium ion

more here
Dimethylsulfoxide

more here
Dimethylsulfoxide, protonated

more here
Dinitromethane

more here
2,4-Dinitrophenol

more here
1,4-Dioxane, protonated

more here
Diphenyl phosphine

more here
Diphenylamine

more here
Diphenylammonium ion

more here
Disulfide (hydrogen) ion

more here
1,2-Dithioethane

more here
1,2-Dithioethane monoanion

more here
Ethane

more here
Ethane thiol

more here
Ethanol

more here
Ethanolamine, protonated

more here
Ethyl acetate

more here
Ethylacetate, protonated

more here
Ethylamine

more here
Ethylammonium ion

more here
Ethylene

more here
Ethylene glycol

more here
Ethylene glycol anion

more here
Ethylenediamine tetraacetic acid

more here
Ethylenediamine, mono-protonated

more here
Ethylenediaminetetraacetic acid dianion

more here
Ethylenediaminetetraacetic acid mono anion

more here
Ethylenediaminetetraacetic acid trianion

more here
Ethylium ion

more here
Ethyloxonium ion

more here
Ethylsulfonium ion

more here
Fluorene

more here
Fluoronium ion

more here
Fluoronium ion, alkyl (generic)

more here
Fluorosulfonic acid

more here
Formic acid

more here
Fumarate (hydrogen) ion

more here
Fumaric acid

more here
Germanate (trihydrogen) ion

more here
Germane

more here
Germane (generic)

more here
Germanic acid

more here
Glycolic acid

more here
Guanidine, protonated

more here
Hydrazine

more here
Hydrazoic acid

more here
Hydrogen bromide

more here
Hydrogen chloride

more here
Hydrogen citrate ion

more here
Hydrogen cyanide

more here
Hydrogen deuterium oxide

more here
Hydrogen fluoride

more here
Hydrogen iodide

more here
Hydrogen peroxide

more here
Hydrogen phosphite ion

more here
Hydrogen selenide

more here
Hydrogen sulfate ion

more here
Hydrogen sulfide

more here
Hydrogen sulfide anion

more here
Hydrogen telluride

more here
Hydroxy carbenium ion

more here
Hydroxyammonium ion

more here
Hydroxydialkoxy carbenium ion (generic)

more here
Hydroxymethyl carbenium ion

more here
Hypobromous acid

more here
Hypochlorous acid

more here
Hypofluouous acid

more here
Hypoiodous acid

more here
Hypophosphorous acid

more here
Imidazole

more here
Imidazonium ion

more here
Imine, dialkyl (generic)

more here
Iodic acid

more here
Iodoacetic acid

more here
Iodonium ion

more here
Iodonium ion, alkyl (generic)

more here
Isocyanic acid

more here
Isopropyl oxonium ion

more here
beta-Ketoaldehyde (generic)

more here
beta-Ketoester (generic)

more here
Kryptonium ion

more here
(+/-) Lactic acid

more here
Maleic acid

more here
Maleic acid monoanion

more here
Malonate (hydrogen) ion

more here
Malonate diester (generic)

more here
Malonic acid

more here
Malononitrile

more here
(+/-) Mandelic acid

more here
Methane

more here
Methane thiol

more here
Methanol

more here
Methoxyacetic acid

more here
4-Methyl-2,6-di-tert-butyl pryidinium ion

more here
Methyl ketone (generic)

more here
Methylamine

more here
Methylammonium ion

more here
Methyloxonium ion

more here
2-Methylpropane

more here
2-Methylpyridinium ion

more here
Methylsulfonium ion

more here
Methylsulfonyl acetic acid

more here
Methylthioacetic acid

more here
Neonium ion

more here
Nitric acid, concentrated

more here
Nitric acid, fuming

more here
Nitric acid, gas phase species

more here
Nitrile (generic)

more here
Nitrilium ion (generic)

more here
Nitro compound (generic)

more here
Nitroacetic acid

more here
Nitrobenzene, protonated

more here
Nitromethane, protonated

more here
3-Nitrophenol

more here
4-Nitrophenol

more here
4-Nitrophenylammonium ion

more here
Nitrosyl hydrogen sulfate

more here
Nitrous acid

more here
Tetrahydroorthoperiodate ion

more here
Orthoperiodic acid

more here
Oxalate monoanion

more here
Oxalic acid

more here
Oxonium ion

more here
2,4-Pentanedione

more here
Peracetic acid

more here
Perchloric acid

more here
Peroxide, organic (generic)

more here
Peroxodisulfate(VI) ion

more here
Peroxodisulfuric acid

more here
Phenol

more here
Phenyl arsine

more here
Phenyl silane

more here
Phenyl telluride

more here
Phenylacetylene

more here
Phenylammonium ion

more here
Phenyloxonium ion

more here
Phosphate dianion, hydrogen

more here
Phosphine

more here
Phosphonate, diethyl 1° alkyl (generic)

more here
Phosphonium ion

more here
Phosphonium ion (generic)

more here
Phosphoric acid

more here
Phosphorus acid

more here
Phthalate (o) (hydrogen) ion

more here
o-Phthalic acid

more here
Phthalimide

more here
Picric acid

more here
Piperidine, protonated

more here
Propane

more here
Propanoic acid

more here
2-Propanol

more here
Propargyl alcohol

more here
1-Propyl ammonium ion

more here
Pyridinium ion

more here
Pyrrolidine, protonated

more here
Pyruvic acid

more here
Salicyate ion

more here
Salicylic acid

more here
Selenite (hydrogen) ion

more here
Selenonium ion

more here
Selenous acid

more here
Selinophenol

more here
Silane

more here
Silane (generic)

more here
Sodium hydrogen sulfite

more here
Stibine

more here
Stibonium ion

more here
(-) Strychnine, protonated

more here
Succinate (hydrogen) ion

more here
Succinic acid

more here
Succinimide

more here
Sulfamic acid

more here
Sulfinic acid (generic)

more here
Sulfonium ion

more here
Sulfonium ion, alkyl (generic)

more here
Sulfonium ion, dialkyl (generic)

more here
Sulfuric acid

more here
Sulfurous acid

more here
d/l-Tartaric acid

more here
Tartrate (hydrogen) ion

more here
Telluride (generic)

more here
Tellurite (hydrogen) ion

more here
Telluronium ion

more here
Tellurous acid

more here
Tetrahydrofuran, protonated

more here
Thiocarbenium ion (generic)

more here
Thiocyanic acid

more here
Thiol (generic)

more here
Thiophenol

more here
p-Toluenesulfonic acid monohydrate

more here
Trichloroacetic acid

more here
2,2,2-Trichloroethanol

more here
Tricyanomethane

more here
Triethylammonium ion

more here
Triethylarsonium ion

more here
Triethylphosphonium ion

more here
Trifluoroacetic acid

more here
2,2,2-Trifluoroethanol

more here
Trifluoromethanesulfonic acid

more here
Trimethylammonium ion

more here
4-(Trimethylammonium) phenol

more here
Trimethylphosphonium ion

more here
2,4,6-Trimethylpyridinium ion

more here
bis(Trimethylsilyl) amine

more here
Trimethylsulfoxonium ion

more here
Trimethylsulfoxonium ylid

more here
Triphenylmethane

more here
Urea, protonated

more here
Water

more here


Interactions and reactions classified as:
Type 3 Lewis Acid/Base Complexation Chemistry
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      2 +1 1
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      1 +1 1 +1
      1 1 +1



Poster
Nucleophiles & Bases

© Mark R. Leach 1999-


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