Interactions | Reactions | Processes

Classified as: Type 15 Lewis Acid/Base Complexation Chemistry

All covalent sigma-bonds can be regarded as Type 15 complexes. Reactions involving Type 15 complexes occur either occur via 1st order sequential mechanisms (decomplexation followed by complexation) or via 1st order concerted mechanisms.

For more information look in the Chemogenesis webbook sections on Lewis acids and Lewis bases and the Lewis acid/base interaction matrix.

BF3
  +  
         

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B2H6
  +  
2
         
2

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  +  
Cl–
         
R–O–CH2CH2Cl

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  +  
Cl–
         
R2N–CH2CH2Cl

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  +  
Cl–
         
R–S–CH2CH2Cl

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R+
  +  
Br–
         
RBr

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R+
  +  
[CN]–
         
R–NC

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  +  
[CN]–
         

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  +  
[CN]–
         

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Cl+
  +  
R–
         
RCl

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R+
  +  
F–
         
R–F

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R+
  +  
I–
         
R–I

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R+
  +  
[H2N]–
         
R–NH2

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  +  
[H2N]–
         

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CO2
  +  
         

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  +  
[CH3]–
         
[(CH3)3C–O]–

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R+
  +  
–S–S–
         
[RSS]–

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  +  
R–CH2O–
         

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R+
  +  
[N3]–
         
R–N3

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R+
  +  
RCOO–
         

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R+
  +  
[RSS]–
         
R–S–S–R

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[CH3CO]+
  +  
[CH3COO]–
         
(CH3CO)2CO

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Br+
  +  
Br–
         
Br2

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Cl+
  +  
Cl–
         
Cl2

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CH2
  +  
N2
         
CH2N2

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Al3+
  +  
[CN]–
  +  
2
[CH3CH2]–
         

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I+
  +  
I–
         
I2

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[CH3]+
  +  
I–
         
CH3I

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[HO]+
  +  
[CH3COO]–
         
CH3COOOH

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  +  
Br–
         

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2
  +  
[CO3]2–
         

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[CH3CO]+
  +  
RO–
         
CH3COOR

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[CH3CO]+
  +  
[H2N]–
         
CH3CONH2

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[RCO]+
  +  
Cl–
         
RCOCl

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2
Al3+
  +  
3
[SO4]2–
         
Al2(SO4)3

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Al3+
  +  
3
[OH]–
         
Al(OH)3

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Sb3+
  +  
3
Cl–
         
SbCl3

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Sb5+
  +  
5
Cl–
         
SbCl5

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As3+
  +  
3
F–
         
AsF3

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As5+
  +  
5
F–
         
AsF5

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Br+
  +  
Cl–
         
BrCl

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[CH3]+
  +  
F–
         
CH3F

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[CH3CH2]+
  +  
F–
         

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  +  
F–
         

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[CH3]+
  +  
Cl–
         
CH3Cl

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[CH3CH2]+
  +  
Cl–
         
CH3CH2Cl

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  +  
Cl–
         

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  +  
F–
         

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  +  
Cl–
         

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[CH3]+
  +  
Br–
         
CH3Br

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[CH3CH2]+
  +  
Br–
         
CH3CH2Br

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  +  
Br–
         
(CH3)2CHBr

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[CH3CH2]+
  +  
I–
         
CH3CH2I

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  +  
I–
         
(CH3)2CHI

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  +  
I–
         
(CH3)3CI

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RCHO
  +  
[CN]–
         

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R–C–H
  +  
         

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Br+
  +  
         

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  +  
Cl–
         

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  +  
Br–
         

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  +  
I–
         

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Cl+
  +  
         

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[RCO]+
  +  
         

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[RCO]+
  +  
         

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  +  
Cl+
         

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Br+
  +  
         

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FeBr3
  +  
Br–
         
[FeBr4]–

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  +  
I+
         

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[NO2]+
  +  
[HSO4]–
  +  
H2O
         
HNO3|H2SO4
concentrated

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R+
  +  
         

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  +  
[CN]–
         

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[RCO]+
  +  
RCOO–
         
(RCOO)2O

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[CH3]+
  +  
RCOO–
         

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R+
  +  
         
R–Nu

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Br+
  +  
         

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[RCH2CH2]+
  +  
[H2N]–
         
RCH2NH2

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R+
  +  
R–
         
R–R

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[RCO]+
  +  
         

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R+
  +  
         

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Br+
  +  
         

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[CH3]+
  +  
[R–S]–
         
R–S–CH3

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[RCH2CH2]+
  +  
         
[(C6H5)3P–CH2R]+

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[CH3CH2]+
  +  
[PO4]3–
         
(CH3CH2O)3P=O

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[CH3CO]+
  +  
[CH3CH2]–
         

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[CH3CO]+
  +  
[(CH3)3C]–
         

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Br+
  +  
R–
         
RBr

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CH2
  +  
         

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  +  
[CN]–
         

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R+
  +  
Cl–
         
RCl

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I+
  +  
R–
         
R–I

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[CH3]+
  +  
[CN]–
         
CH3CN

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R+
  +  
[CN]–
         
R–CN

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[CH3CH2]+
  +  
[H2N]–
         
CH3CH2NH2

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CH3CHO
  +  
[CH3]–
         
[(CH3)2CH–O]–

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  +  
[CH3]–
         
CH3CHO

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[CH3CO]+
  +  
[CH3]–
         

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[CH3CO]+
  +  
[OH]–
         
CH3COOH

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  +  
[OH]–
         
(CH3)3COH

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[RCH2CH2]+
  +  
[OH]–
         
RCH2OH

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[RCO]+
  +  
[H2N]–
         

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R+
  +  
[HS]–
         
R–SH

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R+
  +  
[HTe]–
         
R–TeH

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R+
  +  
NH3
         
[R–NH3]+

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R+
  +  
HBr
         
[R–BrH]+

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[CH3CO]+
  +  
         

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R+
  +  
HCl
         
[R–ClH]+

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R+
  +  
HF
         
[R–FH]+

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R+
  +  
HI
         
[R–IH]+

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  +  
NH3
         

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R+
  +  
H2S
         
[R–SH2]+

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R+
  +  
H2Te
         
[R–TeH2]+

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[RCO]+
  +  
[OH]–
         
RCOOH

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R+
  +  
[HOO]–
         
ROOH

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  +  
H2O
         

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  +  
H2O
         

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  +  
R–
         

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R+
  +  
[OH]–
         
R–OH

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[RCO]+
  +  
RO–
         

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[R–S]+
  +  
[R–S]–
         
R–S–S–R

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I+
  +  
[CH3]–
         
CH3I

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Br+
  +  
         

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Cl+
  +  
[CH3]–
         
CH3Cl

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Cl+
  +  
[CH3CH2]–
         
CH3CH2Cl

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Cl+
  +  
         

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Cl+
  +  
[(CH3)3C]–
         

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Br+
  +  
[CH3]–
         
CH3Br

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Br+
  +  
[CH3CH2]–
         
CH3CH2Br

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Br+
  +  
         
(CH3)2CHBr

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I+
  +  
[CH3CH2]–
         
CH3CH2I

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I+
  +  
         
(CH3)2CHI

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I+
  +  
[(CH3)3C]–
         
(CH3)3CI

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[RCO]+
  +  
[CH3–O]–
         

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[RCO]+
  +  
R–
         

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[R3C]+
  +  
[OH]–
         
R3COH

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  +  
RCOO–
         

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  +  
RO–
         

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[CH3CO]+
  +  
         

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[R–S]+
  +  
[CH3]–
         
R–S–CH3

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Br+
  +  
         
R–CH2–Br

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[NO]+
  +  
[OH]–
         
HNO2

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  +  
         

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  +  
         

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  +  
         

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[CH3CH2]+
  +  
H2O
         
CH3CH2OH
  +  
H+

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[RCH2CH2]+
  +  
H2O
         
R–CH2CH2OH
  +  
H+

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[R2CH]+
  +  
H2O
         
R2CHOH
  +  
H+

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[R3C]+
  +  
H2O
         
R3COH
  +  
H+

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B2H6
  +  
2
(CH3)2S
         
2
(CH3)2S→BH3

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Br+
  +  
Br–
         
Br2(g)

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2
Al3+
  +  
3
O2–
         
Al2O3

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  +  
         

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  +  
         

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R+
  +  
         
R–Nfg

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[R3C]+
  +  
         
(R)3C–Nfg

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[R2CH]+
  +  
         
(R)2CH–Nfg

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[RCH2CH2]+
  +  
         
RCH2–Nfg

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[CH3]+
  +  
         
CH3–Nfg

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  +  
         

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  +  
         

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[RCO]+
  +  
         

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  +  
         

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RMgX
  +  
SO2
         

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RMgX
  +  
SO2
         
[R–SO2]–

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R+
  +  
[NCO]–
         
R–O–C≡N

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R+
  +  
[SCN]–
         
R–N=C=S

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  +  
AlCl3
         
  +  
[AlCl4]–

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CO2
  +  
2
KOH
         
K2CO3
  +  
H2O

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CO2
  +  
2
NaOH
         
Na2CO3
  +  
H2O

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CO2
  +  
[OH]–
         
[HCO3]–

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CO2
  +  
2
[OH]–
         
[CO3]2–
  +  
H2O

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[CO3]2–
  +  
CO2
  +  
H2O
  +  
H2O
         
2
[HCO3]–

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SiF4
  +  
2
F–
         
[SiF6]2–

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N2O4
         
[NO]+
  +  
[NO3]–

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[NO2]+
  +  
[NO3]–
         
N2O5

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SO3
  +  
H2S
  +  
         

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Cl+
  +  
[ClO4]–
         
Cl+ [ClO4]–

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SbF5
  +  
HSO3F
         
ROH
  +  
SO3

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BF3
  +  
ClF3
         
[ClF2]+
  +  
[BF4]–

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SbF5
  +  
ClF3
         
[ClF2]+
  +  
[SbF6]–

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BrF5
  +  
CsF
         
Cs+
  +  
[BrF6]–

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IF5
  +  
KF
         
K+
  +  
[IF6]–

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IF7
  +  
CsF
         
Cs+
  +  
[IF8]–

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I–Cl
  +  
KCl
         
K+
  +  
[ICl2]–

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I2
  +  
I–
         
[I3]–

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I–Cl
  +  
KI
         
K+
  +  
[I2Cl]–

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I2
  +  
I–Cl
  +  
AlCl3
         
[I3]+
  +  
[AlCl4]–

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Cl2
  +  
ClF3
  +  
AsF5
         
[Cl3]+
  +  
[AsF6]–
  +  
F2

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Br2
  +  
BrF3
  +  
AsF5
         
[Br3]+
  +  
[AsF6]–
  +  
F2

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  +  
[OH]–
         

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[NO]+
  +  
H+
  +  
[SO4]2–
         
NOHSO4

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CH3COCl
  +  
AlCl3
         
[CH3CO]+
  +  
[AlCl4]–

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Al(OH)3
  +  
NaOH
         
[Al(OH)4]–
  +  
Na+

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Al(OH)3
  +  
NaOH(aq)
         
[Al(OH)4]–
  +  
Na+

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  +  
Br–
         
(CH3)3CBr

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Be(OH)2
  +  
2
[OH]–
  +  
H2O
         
[Be(OH)4]2–

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Be(OH)2
  +  
2
NaOH(aq)
         
2
Na+
  +  
[Be(OH)4]2–

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AlCl3
  +  
Cl–
         
[AlCl4]–

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  +  
KCN
         
  +  
KBr

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  +  
Br–
         

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  +  
Br–
         

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  +  
Br–
         
(CH3)2CHBr

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[CH3CH2]+
  +  
H2O

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[CH3CH2]+
  +  
Br–
         
CH3CH2Br

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[NO2]+
  +  
H2O

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2
AlCl3
         
Al2Cl6

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© Mark R. Leach 1999 –

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please contact Mark R. Leach, the author, using mark@meta-synthesis.com