Interactions | Reactions | Processes


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Classified as: Type 3 Lewis Acid/Base Complexation Chemistry



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Type 3 complexes form when Proton Lewis acids complex with Lobe-HOMO (lone-pair) Lewis bases. The resulting complexes are Brønsted acids.

In fact the vast majority of organic and inorganic Brønsted acids are Type 3 complexes. The pKa values of Type 3 complex species may vary from less than -12 (HI) to greater than 70 (tertiary alkanes), ie by more than 80 orders of magnitude!

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

H+
  +  
[H2As]–
        
H3As

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H+
  +  
Br–
        
HBr

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H+
  +  
Cl–
        
HCl

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H+
  +  
F–
        
HF

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H+
  +  
I–
        
HI

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H+
  +  
N≡C–CH2–
        
CH3CN

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H+
  +  
        
R–CN

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[NH2–NH]–
        
H2N–NH2

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H+
  +  
[H2N]–
        
NH3

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H+
  +  
        
R2NH

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H+
  +  
        
CH3CH2NH2

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H+
  +  
[CH3–NH]–
        
CH3NH2

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H+
  +  
[(CH3)2N]–
        
(CH3)2NH

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H+
  +  
[SO4]2–
        
[HSO4]–

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H+
  +  
[C2O4]2–
        

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H+
  +  
[H3IO6]2–
        
[H4IO6]–

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H+
  +  
[HPO3]2–
        
[H3PO4]–

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H+
  +  
        

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H+
  +  
[HPO4]2–
        
[H2PO4]–

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H+
  +  
[HAsO4]2–
        
[H2AsO4]–

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H+
  +  
[SeO3]2–
        
[HSeO3]–

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H+
  +  
        

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H+
  +  
[TeO3]2–
        
[HTeO3]–

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[CO3]2–
        
[HCO3]–

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[AsO4]3–
        
[HAsO4]2–

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H+
  +  
[PO4]3–
        
[HPO4]2–

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H+
  +  
[H2GeO4]2–
        
[H3GeO4]–

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        
RCOO–

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[CH3COO]–
        
CH3COOH

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H+
  +  
[(CH3)3C–O]–
        
(CH3)3COH

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H+
  +  
R–CH2O–
        
RCH2OH

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H+
  +  
CH3OH
        

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H+
  +  
[HOO]–
        
HOOH

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H+
  +  
[OH]–
        
H2O

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[H2P]–
        
PH3

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H+
  +  
S2–
        
[HS]–

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H+
  +  
        

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H+
  +  
–S–S–
        
[HSS]–

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H+
  +  
[HS]–
        
H2S

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H+
  +  
[R–S]–
        
R–SH

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H+
  +  
[CH3CH2S]–
        
CH3CH2SH

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H+
  +  
[H2Sb]–
        
H3Sb

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H+
  +  
[HSe]–
        
H2Se

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H+
  +  
[HTe]–
        
H2Te

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H+
  +  
R–TeH
        
R–TeH

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H+
  +  
H2C=CH2
        
[CH3CH2]+

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H+
  +  
HCHO
        

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H+
  +  
NH3
        
[NH4]+

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H+
  +  
R–NH2
        
[R–NH3]+

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H+
  +  
R2NH
        
[R2NH2]+

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H+
  +  
R3N
        
[R3NH]+

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H+
  +  
H2O
        
[H3O]+

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H+
  +  
RCH2OH
        
[RCH2OH2]+

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H+
  +  
        
[R2OH]+

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H+
  +  
H2S
        
[SH3]+

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H+
  +  
R2S
        
[R2SH]+

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H+
  +  
Ar
        
[ArH]+

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H+
  +  
        

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H+
  +  
[R2As]–
        
R2AsH

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H+
  +  
(CH3H2)3As
        
[(CH3CH2)3AsH]+

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H+
  +  
H3As
        
[AsH4]+

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H+
  +  
R3As
        
[R3AsH]+

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H+
  +  
HCl
        
[ClH2]+

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H+
  +  
RBr
        
[R–BrH]+

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H+
  +  
HBr
        
[BrH2]+

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H+
  +  
        

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H+
  +  
[(CN)3C]–
        
(CN)3CH

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H+
  +  
[(NO2)2CH]–
        
(NO2)2CH2

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[CN]–
        
HCN

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H+
  +  
        

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H+
  +  
        
R–NO2

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H+
  +  
        

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H+
  +  
[(CN)2CH]–
        
(CN)2CH2

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
HC≡C–
        
HC≡CH

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        
H2C=CH2

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H+
  +  
        

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H+
  +  
[CH3]–
        
CH4

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[CH3CH2]–
        
CH3CH3

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
[R3C]–
        

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H+
  +  
[(CH3)3C]–
        

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H+
  +  
RCl
        
[R–ClH]+

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H+
  +  
HF
        
[FH2]+

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H+
  +  
R–F
        
[R–FH]+

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H+
  +  
[R3Ge]–
        
R3GeH

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H+
  +  
[H3Ge]–
        
GeH4

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H+
  +  
HI
        
[IH2]+

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H+
  +  
R–I
        
[R–IH]+

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H+
  +  
Kr
        
[KrH]+

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H+
  +  
[N3]–
        
HN3

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H+
  +  
[NCO]–
        
HNCO

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
CH3CN
        

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H+
  +  
R–CN
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
H2N–OH
        
[H3N-OH]+

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H+
  +  
        

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H+
  +  
        

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H+
  +  
        

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H+
  +  
(CH3)3N
        
[(CH3)3NH]+

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H+
  +  
        

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H+
  +  
        

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H+
  +  
CH3CH2NH2
        
[CH3CH2NH3]+

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H+
  +  
CH3NH2
        
[CH3NH3]+

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H+
  +  
(CH3CH2)3N
        
[(CH3CH2)3NH]+

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H+
  +  
(CH3)2NH
        
[(CH3)2NH2]+

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H+
  +  
        

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
Ne
        
[NeH]+

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H+
  +  
PH3
        
[PH4]+

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H+
  +  
R3P
        
[R3PH]+

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H+
  +  
(CH3CH2)3P
        
[(CH3CH2)3PH]+

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H+
  +  
(CH3)3P
        
[(CH3)3PH]+

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H+
  +  
        

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H+
  +  
[SCN]–
        
N≡C–SH

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H+
  +  
        

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H+
  +  
CH3CH2SH
        
[CH3CH2SH2]+

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H+
  +  
CH3–SH
        
[CH3–SH2]+

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H+
  +  
[CH3–S]–
        
CH3–SH

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H+
  +  
R–SH
        
[R–SH2]+

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H+
  +  
        

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H+
  +  
(CH3)2S
        
[(CH3)2SH]+

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H+
  +  
(CH3CH2)2S
        
[(CH3CH2)2SH]+

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H+
  +  
[R–SO2]–
        

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H+
  +  
[HSS]–
        
HSSH

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H+
  +  
        

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H+
  +  
H3Sb
        
[SbH4]+

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H+
  +  
        

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H+
  +  
H2Se
        
[SeH3]+

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H+
  +  
        

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H+
  +  
[H3Si]–
        
SiH4

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H+
  +  
[R3Si]–
        
R3SiH

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H+
  +  
H2Te
        
[TeH3]+

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H+
  +  
        

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H+
  +  
R–TeH
        
[R–TeH2]+

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H+
  +  
H2Te
        
[R2TeH]+

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H+
  +  
[ClO4]–
        
HClO4

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H+
  +  
[HSO4]–
        
H2SO4

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H+
  +  
[FSO3]–
        
HSO3F

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H+
  +  
[CF3SO3]–
        
CF3SO3H

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H+
  +  
[NO3]–
        
HNO3

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H+
  +  
[CF3COO]–
        
CF3COOH

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H+
  +  
        

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H+
  +  
[CCl3COO]–
        
CCl3COOH

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H+
  +  
        

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H+
  +  
  +  
H2O
        

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H+
  +  
[IO3]–
        
HIO3

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H+
  +  
[NH2SO3]–
        
H2NSO3H

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H+
  +  
        

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H+
  +  
[CHCl2COO]–
        
CHCl2COOH

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H+
  +  
[H4IO6]–
        
H5IO6

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H+
  +  
        

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H+
  +  
[H3PO4]–
        
H3PO3

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H+
  +  
        
CH3CH2COOH

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H+
  +  
[ClO2]–
        
HClO2

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H+
  +  
[H2PO2]–
        
H3PO2

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
[H2PO4]–
        
H3PO4

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H+
  +  
[H2AsO4]–
  +  
H2O
        
H3AsO4

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H+
  +  
        

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

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H+
  +  
[HSeO3]–
        
H2SeO3

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H+
  +  
[HTeO3]–
        
H2TeO3

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
[ClCH2COO]–
        
CH2ClCOOH

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H+
  +  
[BrCH2COO]–
        
CH2BrCOOH

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
[ICH2COO]–
        
CH2ICOOH

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H+
  +  
[NO2]–
        
HNO2

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H+
  +  
        

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H+
  +  
[HCOO]–
        
HCOOH

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
CH3COOH
        

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

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H+
  +  
[HCO3]–
        
H2CO3

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

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H+
  +  
[ClO]–
        
HClO

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H+
  +  
        

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H+
  +  
[BrO]–
        
HOBr

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H+
  +  
[HSO3]–
        
H2SO3

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H+
  +  
[SO3]2–
        
[HSO3]–

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
CH3–NO2
        

Go To Reaction Data Page
H+
  +  
RCHO
        

Go To Reaction Data Page
H+
  +  
CH3CHO
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
RCOO–
        
RCOOH

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H+
  +  
RCOOH
        

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H+
  +  
[H3GeO4]–
        
H4GeO4

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H+
  +  
[IO]–
        
HOI

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H+
  +  
        
CCl3CH2OH

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H+
  +  
        
CF3CH2OH

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H+
  +  
        
HC≡CCH2OH

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H+
  +  
[ROO]–
        
ROOH

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H+
  +  
[CH3–O]–
        
CH3OH

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
CH3CH2OH
        

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H+
  +  
CH3CH2O–
        
CH3CH2OH

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H+
  +  
(CH3)3COH
        

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
[(CH3)2CH–O]–
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        
R–CH3

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
RO–
        
R–OH

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
CH2
        
[CH3]+

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H+
  +  
        

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H+
  +  
Base–
Proton abstractor
        
Base-H
Protonated base

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H+
  +  
Base:
Proton abstractor
        

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

Go To Reaction Data Page
H+
  +  
        
R3COH

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
        

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H+
  +  
[BF4]–
        
HBF4(aq)

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H+
  +  
        

Go To Reaction Data Page
H+
  +  
Cl–
        
HCl(aq)

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H+
  +  
Cl–
  +  
H2O
        
HCl(conc)

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H+
  +  
[HSO4]–
        
H2SO4(aq)

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H+
  +  
[NO3]–
        
HNO3(aq)

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H+
  +  
[CH3COO]–
  +  
H2O
        
CH3COOH(aq)

Go To Reaction Data Page
H+
  +  
[NO3]–
        
HNO3
5 molar

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  +  
        

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H+
  +  
R–C≡C–
        
R–C≡C–H

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H+
  +  
[R–S–CH2]–
        
R–S–CH3

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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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3
H+
  +  
3
        
3

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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
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H+
  +  
–C≡C–
        
HC≡C–

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4
H+
  +  
C4–
        
CH4

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H+
  +  
[BO2]–
[B3O6]3–
        
HBO2

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2
H+
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2
H+
  +  
        

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2
H+
  +  
        

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2
H+
  +  
        

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2
HF
        
H+
  +  
[FHF]–

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H+
  +  
[FO]–
        
HOF

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H+
  +  
[ClO3]–
        
HClO3

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H+
  +  
[BrO3]–
        
HBrO3

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H+
  +  
[IO4]–
        
HIO4

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H+
  +  
CH4
        
[CH5]+

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H+
  +  
CO
        

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

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2
H+
  +  
[SiF6]2–
        
H2SiF6(aq)

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H+
  +  
[O=N=C]–
        
H–O=N=C

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HNO3
  +  
H2SO4
        
  +  
[HSO4]–

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HNO3|H2SO4
concentrated
        
  +  
[HSO4]–

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© Mark R. Leach 1999 –

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