Lewis Acid/Base Interaction Matrix Database


Type 15 Lewis Acid/Base Complexation Chemistry
Classical Organic Chemistry: SN1, SN2, SE1, SE2 Pathways

               R3C+      +      Cl              R3C–Cl

Bonding:

The normal strong covalent and polarised covalent s-bonds of main group chemistry are generally Lobe-LUMO/Lobe-HOMO complexes:

C-C    C-N    C-O    C-F    C-Br     C-Nu    C-Nfg    Cl-Cl   O-O   S-Cl     P-Br    B-N+   etc.

In solution Lobe-LUMO/Lobe-HOMO complexes may be covalently bonded, polar-covalently bonded or strongly ion-paired, weakly ion-paired or solvent separated.

Charge: Complexes may be negatively or positively charged or they may be neutral.
Chemistry:

Prochiral tertiary carbenium ions – carbenium ions with three different ligands and a solvent separated Lobe-HOMO Lewis Base counter ion – react with nucleophiles to give racemic mixtures of enantiomers:

Chiral sp3 carbon/nucleofuge complexes react with nucleophiles via a concerted SN2 mechanistic process in which the chiral centre inverts ‘like an umbrella’, a 'Walden inversion'.

Strong ion-pairing makes concerted second order substitution more favorable than step-wise first order reactivity.

Acyl chlorides and other carbonyl/Nfg complexes also undergo concerted nucleophilic substitution, although the mechanism is rather different:

Congeneric Series:

There are many congeneric series and planars, for example:

Type 15 Lewis acid/base complex (generic)
Acetal (generic)

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Acetal, cyclic (generic)

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Acetaldehyde

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Acetamide

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Acetate ester (generic)

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Acetic acid

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Acetic anhydride

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Acetone

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Acetonitrile

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Acid chloride (generic)

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Acid isothiocyanate (generic)

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Alcohol (generic)

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1° Alcohol (generic)

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2° Alcohol (generic)

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3° Alcohol (generic)

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Alkyl bromide (generic)

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1° Alkyl bromide (generic)

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2° Alkyl bromide (generic)

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Alkyl chloride (generic)

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2° Alkyl chloride (generic)

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2° Alkyl iodide (generic)

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1° Alkyl oxonium ion (generic)

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Alkyl telluronium ion (generic)

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Alkyl, R-R (generic)

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Alkylated nucleophile (generic)

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Aluminium chloride dimer

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Aluminium hydroxide

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Aluminium isopropoxide

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Aluminium oxide

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Aluminium sulfate

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1° Amide (generic)

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1° Amine (generic)

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1° Amine, 1° alkyl (generic)

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2 Amine, (RCH2)2NH (generic)

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2° Amine, R, R- (generic)

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1° Ammonium ion (generic)

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Anhydride (generic)

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Antimony sulfide

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Antimony(III) chloride

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Antimony(v) chloride

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Arsenic(III) fluoride

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Arsenic(III) sulfide

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Arsenic(V) fluoride

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Azide (generic)

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Benzene, substituted (generic)

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Benzonitrile

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Benzyl isocyanide

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Borane/Methylsulfide complex

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Borane/THF Complex

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Boron nitride, hexagonal

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Boron sulfide

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Boron trifluoride etherate

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Bromine

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Bromine chloride

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alpha-Bromoaldehyde (generic)

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Bromobenzene

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Bromoethane

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Bromomethane

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alpha-Bromomethyl ketone (generic)

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Bromonium ion, alkyl (generic)

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1-Bromopropane

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N-Bromosuccinimide

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tertiary Butanol

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Butanone

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tertiary Butyl alkoxide

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1-Butylamine

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1-Butylammonium ion

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n Butylisocyanide

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tertiary Butyl isocyanide

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tertiary Butyl oxonium ion

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Carbonyl, alkylated (generic)

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Carboxylic acid (generic)

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Chlorine

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2-Chloro-2-methylpropane

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Chlorobenzene

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Chloroethane

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beta-Chloroethyl amine (generic)

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beta-Chloroethyl ether (generic)

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beta-Chloroethyl thioether (generic)

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Chloromethane

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Chloronium ion, alkyl (generic)

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meta Chloroperoxybenzoic acid

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2-Chloropropane

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Cyanohydrin, alkyl (generic)

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Cyclohexyl isocyanide

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Cyclopentane carboxylate ion

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Diazomethane

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Di-tertary-butoxycarbonate

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Diethyl aluminium cyanide

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Diethyl sulfate

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3,3-Dimethyl-2-butanone

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Dinitrogen pentoxide

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Disulfide anion, organic (generic)

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Disulfide, organic (generic)

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Ester (generic)

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Ethyl acetoacetate

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Ethyl fluoride

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Ethylamine

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Fluoride, organic (generic)

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2-Fluoro-2-methylpropane

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Fluoromethane

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Fluoronium ion, alkyl (generic)

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2-Fluoropropane

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Formate ester (generic)

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Hexafluoroantimonate(V)

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beta-Hydroxy aldehyde (generic)

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Iodide, organic (generic)

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Iodine

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Iodobenzene

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Iodoethane

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2-Iodo-2-methyl propane

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Iodonium ion, alkyl (generic)

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Isocyanide (generic)

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Isopropyl alkoxide ion

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Isopropyl oxonium ion

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Ketone (generic)

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Ketone, alkyl phenyl (generic)

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Ketone, gamma-alkyl (generic)

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Methyl ester (generic)

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Methyl iodide

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Methyl thioether (generic)

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Methylphenylsulfinate

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Nitrating mixture

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Nitrile (generic)

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Nitrosyl hydrogen sulfate

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Oxalyl chloride

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2,4-Pentanedione

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Peracetic acid

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Peroxide, organic (generic)

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Phenyl ester (generic)

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Phenyl ether (generic)

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Phenyl selenenyl bromide

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Phosphate di-substituted (generic)

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Phosphate tri-substituted (generic)

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Phosphate, mono-substituted (generic)

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Phosphonium ion, alkyl triphenyl (generic)

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Phosphorus pentachloride

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Phosphorus pentachloride g

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2-Propyl bromide

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2-Propyliodide

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Sulfonium ion, alkyl (generic)

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Telluride (generic)

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Tetrabromoaluminate

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Tetrabromoborate

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Tetrabromoferrate ion

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Tetrachloroaluminium ion

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Tetrafluoroaluminate

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Tetrafluoroborate ion

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Tetrahydroxyborate ion

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Tetraiodoaluminate

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Tetraiodoborate

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Thiocyanate (generic)

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Thiol (generic)

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Triethylphosphate

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Triiodide ion

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Trimethylsulfoxonium ylid

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Vinyl chloride (generic)

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Wittig reagent (generic)

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Interactions and reactions classified as:
Type 15 Lewis Acid/Base Complexation Chemistry
      1 +1 1
      1 +2 2
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 +2 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      2 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      2 +3 1
      1 +3 1
      1 +3 1
      1 +5 1
      1 +3 1
      1 +5 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +2 2
      1 +1 1
      2 +3 1
       +
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1 +1
      1 +2 1 +1
      1 +2 1 +1
      1 +1 1
      1 +2 1 +1
      1 +1 +1 + 2
      1 +2 1
      1 1 +1
      1 +1 1
      1 +1 + 1
      1 +1 1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1
      1 +1 1 +1
      1 +1 +1 1 +1
      1 +1 +1 1 +1 +1
      1 +1 +1 1 +1 +1
      1 +1 1
      1 +1 +1 1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1 +1
      1 +1 1
      1 +2 + 1
      1 +2 2 +1
      1 +1 1
      1 +1 1 +1
      1 +1 1
      1 +1 1
      1 +1 1
      1 1 +1
      1 +1 1
      1 1 +1
      2 1



Poster
Nucleophiles & Bases

© Mark R. Leach 1999-


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