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Interactions | Reactions | Processes
Classified as: Type 3 Lewis Acid/Base Complexation Chemistry
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.![](http://www.chemthes.com/mech/103.gif)
H+ |
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[H2As]– |
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H3As |
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Br– |
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HBr |
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Cl– |
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HCl |
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F– |
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HF |
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I– |
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HI |
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H+ |
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N≡C–CH2– |
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CH3CN |
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H+ |
+ |
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R–CN |
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H+ |
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[NH2–NH]– |
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H2N–NH2 |
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H+ |
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[H2N]– |
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NH3 |
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R2NH |
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H+ |
+ |
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CH3CH2NH2 |
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H+ |
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[CH3–NH]– |
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CH3NH2 |
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H+ |
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[(CH3)2N]– |
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(CH3)2NH |
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H+ |
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[SO4]2– |
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[HSO4]– |
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[C2O4]2– |
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H+ |
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[H3IO6]2– |
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[H4IO6]– |
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H+ |
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[HPO3]2– |
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[H3PO4]– |
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[HPO4]2– |
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[H2PO4]– |
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H+ |
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[HAsO4]2– |
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[H2AsO4]– |
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H+ |
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[SeO3]2– |
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[HSeO3]– |
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[TeO3]2– |
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[HTeO3]– |
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H+ |
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[CO3]2– |
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[HCO3]– |
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H+ |
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[AsO4]3– |
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[HAsO4]2– |
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H+ |
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[PO4]3– |
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[HPO4]2– |
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H+ |
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[H2GeO4]2– |
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[H3GeO4]– |
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RCOO– |
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H+ |
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[CH3COO]– |
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CH3COOH |
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H+ |
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[(CH3)3C–O]– |
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(CH3)3COH |
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H+ |
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R–CH2O– |
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RCH2OH |
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H+ |
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CH3OH |
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H+ |
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[HOO]– |
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HOOH |
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H+ |
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[OH]– |
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H2O |
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H+ |
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[H2P]– |
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PH3 |
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H+ |
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S2– |
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[HS]– |
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H+ |
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–S–S– |
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[HSS]– |
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H+ |
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[HS]– |
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H2S |
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H+ |
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[R–S]– |
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R–SH |
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H+ |
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[CH3CH2S]– |
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CH3CH2SH |
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H+ |
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[H2Sb]– |
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H3Sb |
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H+ |
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[HSe]– |
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H2Se |
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H+ |
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[HTe]– |
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H2Te |
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H+ |
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R–TeH |
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R–TeH |
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H+ |
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H2C=CH2 |
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[CH3CH2]+ |
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H+ |
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HCHO |
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H+ |
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NH3 |
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[NH4]+ |
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H+ |
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R–NH2 |
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[R–NH3]+ |
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H+ |
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R2NH |
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[R2NH2]+ |
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H+ |
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R3N |
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[R3NH]+ |
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H+ |
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H2O |
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[H3O]+ |
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H+ |
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RCH2OH |
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[RCH2OH2]+ |
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H+ |
+ |
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[R2OH]+ |
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H+ |
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H2S |
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[SH3]+ |
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H+ |
+ |
R2S |
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[R2SH]+ |
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H+ |
+ |
Ar |
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[ArH]+ |
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H+ |
+ |
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H+ |
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[R2As]– |
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R2AsH |
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H+ |
+ |
(CH3H2)3As |
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[(CH3CH2)3AsH]+ |
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H+ |
+ |
H3As |
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[AsH4]+ |
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H+ |
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R3As |
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[R3AsH]+ |
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H+ |
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HCl |
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[ClH2]+ |
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H+ |
+ |
RBr |
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[R–BrH]+ |
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H+ |
+ |
HBr |
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[BrH2]+ |
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H+ |
+ |
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H+ |
+ |
[(CN)3C]– |
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(CN)3CH |
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H+ |
+ |
[(NO2)2CH]– |
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(NO2)2CH2 |
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+ |
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H+ |
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[CN]– |
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HCN |
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H+ |
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H+ |
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R–NO2 |
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H+ |
+ |
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H+ |
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[(CN)2CH]– |
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(CN)2CH2 |
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H+ |
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H+ |
+ |
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H+ |
+ |
HC≡C– |
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HC≡CH |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
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H2C=CH2 |
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H+ |
+ |
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H+ |
+ |
[CH3]– |
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CH4 |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
[CH3CH2]– |
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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 |
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[R–ClH]+ |
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H+ |
+ |
HF |
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[FH2]+ |
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H+ |
+ |
R–F |
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[R–FH]+ |
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H+ |
+ |
[R3Ge]– |
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R3GeH |
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H+ |
+ |
[H3Ge]– |
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GeH4 |
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H+ |
+ |
HI |
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[IH2]+ |
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H+ |
+ |
R–I |
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[R–IH]+ |
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H+ |
+ |
Kr |
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[KrH]+ |
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H+ |
+ |
[N3]– |
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HN3 |
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H+ |
+ |
[NCO]– |
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HNCO |
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H+ |
+ |
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H+ |
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CH3CN |
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H+ |
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R–CN |
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H+ |
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H+ |
+ |
H2N–OH |
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[H3N-OH]+ |
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H+ |
+ |
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H+ |
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(CH3)3N |
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[(CH3)3NH]+ |
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H+ |
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H+ |
+ |
CH3CH2NH2 |
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[CH3CH2NH3]+ |
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H+ |
+ |
CH3NH2 |
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[CH3NH3]+ |
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H+ |
+ |
(CH3CH2)3N |
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[(CH3CH2)3NH]+ |
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H+ |
+ |
(CH3)2NH |
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[(CH3)2NH2]+ |
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H+ |
+ |
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H+ |
+ |
Ne |
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[NeH]+ |
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H+ |
+ |
PH3 |
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[PH4]+ |
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H+ |
+ |
R3P |
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[R3PH]+ |
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H+ |
+ |
(CH3CH2)3P |
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[(CH3CH2)3PH]+ |
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H+ |
+ |
(CH3)3P |
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[(CH3)3PH]+ |
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H+ |
+ |
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H+ |
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[SCN]– |
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N≡C–SH |
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H+ |
+ |
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H+ |
+ |
CH3CH2SH |
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[CH3CH2SH2]+ |
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H+ |
+ |
CH3–SH |
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[CH3–SH2]+ |
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H+ |
+ |
[CH3–S]– |
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CH3–SH |
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H+ |
+ |
R–SH |
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[R–SH2]+ |
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H+ |
+ |
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H+ |
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(CH3)2S |
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[(CH3)2SH]+ |
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H+ |
+ |
(CH3CH2)2S |
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[(CH3CH2)2SH]+ |
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H+ |
+ |
[R–SO2]– |
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H+ |
+ |
[HSS]– |
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HSSH |
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H+ |
+ |
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H+ |
+ |
H3Sb |
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[SbH4]+ |
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H+ |
+ |
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H+ |
+ |
H2Se |
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[SeH3]+ |
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H+ |
+ |
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H+ |
+ |
[H3Si]– |
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SiH4 |
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H+ |
+ |
[R3Si]– |
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R3SiH |
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H+ |
+ |
H2Te |
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[TeH3]+ |
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H+ |
+ |
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H+ |
+ |
R–TeH |
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[R–TeH2]+ |
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H+ |
+ |
H2Te |
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[R2TeH]+ |
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H+ |
+ |
[ClO4]– |
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HClO4 |
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H+ |
+ |
[HSO4]– |
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H2SO4 |
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H+ |
+ |
[FSO3]– |
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HSO3F |
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H+ |
+ |
[CF3SO3]– |
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CF3SO3H |
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H+ |
+ |
[NO3]– |
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HNO3 |
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H+ |
+ |
[CF3COO]– |
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CF3COOH |
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H+ |
+ |
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H+ |
+ |
[CCl3COO]– |
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CCl3COOH |
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H+ |
+ |
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H+ |
+ |
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H2O |
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H+ |
+ |
[IO3]– |
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HIO3 |
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H+ |
+ |
[NH2SO3]– |
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H2NSO3H |
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H+ |
+ |
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H+ |
+ |
[CHCl2COO]– |
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CHCl2COOH |
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H+ |
+ |
[H4IO6]– |
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H5IO6 |
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H+ |
+ |
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H+ |
+ |
[H3PO4]– |
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H3PO3 |
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H+ |
+ |
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CH3CH2COOH |
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H+ |
+ |
[ClO2]– |
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HClO2 |
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H+ |
+ |
[H2PO2]– |
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H3PO2 |
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H+ |
+ |
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H+ |
+ |
[H2PO4]– |
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H3PO4 |
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H+ |
+ |
[H2AsO4]– |
+ |
H2O |
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H3AsO4 |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
[HSeO3]– |
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H2SeO3 |
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H+ |
+ |
[HTeO3]– |
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H2TeO3 |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
[ClCH2COO]– |
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CH2ClCOOH |
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H+ |
+ |
[BrCH2COO]– |
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CH2BrCOOH |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
[ICH2COO]– |
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CH2ICOOH |
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H+ |
+ |
[NO2]– |
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HNO2 |
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H+ |
+ |
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H+ |
+ |
[HCOO]– |
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HCOOH |
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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+ |
+ |
CH3COOH |
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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+ |
+ |
[HCO3]– |
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H2CO3 |
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H+ |
+ |
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H+ |
+ |
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H+ |
+ |
[ClO]– |
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HClO |
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[BrO]– |
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HOBr |
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H+ |
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[HSO3]– |
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H2SO3 |
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H+ |
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[SO3]2– |
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[HSO3]– |
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CH3–NO2 |
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H+ |
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RCHO |
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CH3CHO |
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H+ |
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RCOO– |
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RCOOH |
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RCOOH |
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[H3GeO4]– |
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H4GeO4 |
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[IO]– |
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HOI |
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CCl3CH2OH |
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CF3CH2OH |
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HC≡CCH2OH |
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[ROO]– |
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ROOH |
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[CH3–O]– |
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CH3OH |
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CH3CH2OH |
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H+ |
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CH3CH2O– |
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CH3CH2OH |
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H+ |
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(CH3)3COH |
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[(CH3)2CH–O]– |
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R–CH3 |
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RO– |
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R–OH |
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H+ |
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CH2 |
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[CH3]+ |
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H+ |
+ |
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H+ |
+ |
Base– Proton abstractor |
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Base-H Protonated base |
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H+ |
+ |
Base: Proton abstractor |
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R3COH |
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H+ |
+ |
[BF4]– |
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HBF4(aq) |
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H+ |
+ |
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H+ |
+ |
Cl– |
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HCl(aq) |
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H+ |
+ |
Cl– |
+ |
H2O |
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HCl(conc) |
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H+ |
+ |
[HSO4]– |
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H2SO4(aq) |
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H+ |
+ |
[NO3]– |
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HNO3(aq) |
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H+ |
+ |
[CH3COO]– |
+ |
H2O |
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CH3COOH(aq) |
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H+ |
+ |
[NO3]– |
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HNO3 5 molar |
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+ |
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H+ |
+ |
R–C≡C– |
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R–C≡C–H |
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H+ |
+ |
[R–S–CH2]– |
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R–S–CH3 |
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3 |
H+ |
+ |
3 |
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3 |
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H+ |
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–C≡C– |
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HC≡C– |
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4 |
H+ |
+ |
C4– |
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CH4 |
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H+ |
+ |
[BO2]– [B3O6]3– |
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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 |
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H+ |
+ |
[FHF]– |
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H+ |
+ |
[FO]– |
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HOF |
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H+ |
+ |
[ClO3]– |
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HClO3 |
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H+ |
+ |
[BrO3]– |
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HBrO3 |
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H+ |
+ |
[IO4]– |
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HIO4 |
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H+ |
+ |
CH4 |
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[CH5]+ |
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H+ |
+ |
CO |
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[NO]+ |
+ |
H+ |
+ |
[SO4]2– |
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NOHSO4 |
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2 |
H+ |
+ |
[SiF6]2– |
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H2SiF6(aq) |
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H+ |
+ |
[O=N=C]– |
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H–O=N=C |
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HNO3 |
+ |
H2SO4 |
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+ |
[HSO4]– |
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HNO3|H2SO4 concentrated |
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+ |
[HSO4]– |
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© Mark R. Leach 1999 –
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