Lewis Acid/Base Interaction Matrix Database

Type 15 Lewis Acid/Base Complexation Chemistry
Classical Organic Chemistry: S_n1, S_n2, SE1, SE2 Pathways

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 S_n2 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) more here
	Acetal, cyclic (generic) more here
	Acetaldehyde more here
	Acetamide more here
	Acetate ester (generic) more here
	Acetic acid more here
	Acetic anhydride more here
	Acetone more here
	Acetonitrile more here
	Acid chloride (generic) more here
	Acid isothiocyanate (generic) more here
	Alcohol (generic) more here
	1° Alcohol (generic) more here
	2° Alcohol (generic) more here
	3° Alcohol (generic) more here
	Alkyl bromide (generic) more here
	1° Alkyl bromide (generic) more here
	2° Alkyl bromide (generic) more here
	Alkyl chloride (generic) more here
	2° Alkyl chloride (generic) more here
	2° Alkyl iodide (generic) more here
	1° Alkyl oxonium ion (generic) more here
	Alkyl telluronium ion (generic) more here
	Alkyl, R-R (generic) more here
	Alkylated nucleophile (generic) more here
	Aluminium chloride dimer more here
	Aluminium hydroxide more here
	Aluminium isopropoxide more here
	Aluminium oxide more here
	Aluminium sulfate more here
	1° Amide (generic) more here
	1° Amine (generic) more here
	1° Amine, 1° alkyl (generic) more here
	2 Amine, (RCH2)2NH (generic) more here
	2° Amine, R, R- (generic) more here
	1° Ammonium ion (generic) more here
	Anhydride (generic) more here
	Antimony sulfide more here
	Antimony(III) chloride more here
	Antimony(v) chloride more here
	Arsenic(III) fluoride more here
	Arsenic(III) sulfide more here
	Arsenic(V) fluoride more here
	Azide (generic) more here
	Benzene, substituted (generic) more here
	Benzonitrile more here
	Benzyl isocyanide more here
	Borane/Methylsulfide complex more here
	Borane/THF Complex more here
	Boron nitride, hexagonal more here
	Boron sulfide more here
	Boron trifluoride etherate more here
	Bromine more here
	Bromine chloride more here
	alpha-Bromoaldehyde (generic) more here
	Bromobenzene more here
	Bromoethane more here
	Bromomethane more here
	alpha-Bromomethyl ketone (generic) more here
	Bromonium ion, alkyl (generic) more here
	1-Bromopropane more here
	N-Bromosuccinimide more here
	tertiary Butanol more here
	Butanone more here
	tertiary Butyl alkoxide more here
	1-Butylamine more here
	1-Butylammonium ion more here
	n-Butylisocyanide more here
	tertiary Butyl isocyanide more here
	tertiary Butyl oxonium ion more here
	Carbonyl, alkylated (generic) more here
	Carboxylic acid (generic) more here
	Chlorine more here
	2-Chloro-2-methylpropane more here
	Chlorobenzene more here
	Chloroethane more here
	beta-Chloroethyl amine (generic) more here
	beta-Chloroethyl ether (generic) more here
	beta-Chloroethyl thioether (generic) more here
	Chloromethane more here
	Chloronium ion, alkyl (generic) more here
	meta Chloroperoxybenzoic acid more here
	2-Chloropropane more here
	Cyanohydrin, alkyl (generic) more here
	Cyclohexyl isocyanide more here
	Cyclopentane carboxylate ion more here
	Diazomethane more here
	Di-tertary-butoxycarbonate more here
	Diethyl aluminium cyanide more here
	Diethyl sulfate more here
	3,3-Dimethyl-2-butanone more here
	Dinitrogen pentoxide more here
	Disulfide anion, organic (generic) more here
	Disulfide, organic (generic) more here
	Ester (generic) more here
	Ethyl acetoacetate more here
	Ethyl fluoride more here
	Ethylamine more here
	Fluoride, organic (generic) more here
	2-Fluoro-2-methylpropane more here
	Fluoromethane more here
	Fluoronium ion, alkyl (generic) more here
	2-Fluoropropane more here
	Formate ester (generic) more here
	Hexafluoroantimonate(V) more here
	beta-Hydroxy aldehyde (generic) more here
	Iodide, organic (generic) more here
	Iodine more here
	Iodobenzene more here
	Iodoethane more here
	2-Iodo-2-methyl propane more here
	Iodonium ion, alkyl (generic) more here
	Isocyanide (generic) more here
	Isopropyl alkoxide ion more here
	Isopropyl oxonium ion more here
	Ketone (generic) more here
	Ketone, alkyl phenyl (generic) more here
	Ketone, gamma-alkyl (generic) more here
	Methyl ester (generic) more here
	Methyl iodide more here
	Methyl thioether (generic) more here
	Methylphenylsulfinate more here
	Nitrating mixture more here
	Nitrile (generic) more here
	Nitrosyl hydrogen sulfate more here
	Oxalyl chloride more here
	2,4-Pentanedione more here
	Peracetic acid more here
	Peroxide, organic (generic) more here
	Phenyl ester (generic) more here
	Phenyl ether (generic) more here
	Phenyl selenenyl bromide more here
	Phosphate di-substituted (generic) more here
	Phosphate tri-substituted (generic) more here
	Phosphate, mono-substituted (generic) more here
	Phosphonium ion, alkyl triphenyl (generic) more here
	Phosphorus pentachloride more here
	Phosphorus pentachloride g more here
	2-Propyl bromide more here
	2-Propyliodide more here
	Sulfonium ion, alkyl (generic) more here
	Telluride (generic) more here
	Tetrabromoaluminate more here
	Tetrabromoborate more here
	Tetrabromoferrate ion more here
	Tetrachloroaluminium ion more here
	Tetrafluoroaluminate more here
	Tetrafluoroborate ion more here
	Tetrahydroxyborate ion more here
	Tetraiodoaluminate more here
	Tetraiodoborate more here
	Thiocyanate (generic) more here
	Thiol (generic) more here
	Triethylphosphate more here
	Triiodide ion more here
	Trimethylsulfoxonium ylid more here
	Vinyl chloride (generic) more here
	Wittig reagent (generic) more here

Lewis Acid/Base Interaction Matrix Database

Type 15 Lewis Acid/Base Complexation Chemistry