HClO₄


ClO₄^– 

–10

–9

R₂C(=O⁺H)
(protonated ketone)

R₂C(=O)

(ketone) 

–7

RC(=O⁺H)OR'
^{(protonated ester)}

RC(=O)OR'
(ester)

–6

R—O⁺H—R'
(protonated ether)

R—O—R'

(ether) 

–3.5

ROH₂⁺
 (protonated alcohol)

ROH

(alcohol)

–2

H₃O⁺

H₂O 

HNO₃

NO₃^– 

–1.4

2

HF

F^– 

3.1

9.2

9.2

10

10

MeC(=O)NH₂
(acetamide)

MeC(=O)NH^– 

MeOC(=O)CH₃
(ester)

MeOC(=O)CH₂^– 

RCCH
(terminal alkyne)

RCC^– 

Ph—CH₃
(toluene)

Ph—CH₂^–