CHM 244 - nucleophile strength (formulas)

H₂S

hydrogen sulfide

pka = 7

moderate

R₂S

moderate

R-SH

thiol

pka = 10-12

moderate

NH₃

ammonia

pka = 32-38

moderate

RNH₂

moderate

R₂NH

moderate

R₃N

moderate

moderate

stronger nucleophiles have a __________ charge

negative

SR^-

strong

SH^-

strong

CN^-

cyanide

strong

OR^-

strong

OH^-

hydroxide

pka = -1.7

strong

NH₂^-

strong

NHR^-

strong

NR₂^-

strong

CH₃^-

strong

CH₂CH₃^-

ethane

strong

strong

strong

strong

I^-

strong nucleophile

H₂O

pka = 15.7

weak

R-OH

alcohol

pka = 16-18

weak

carboxylic acid

pka = 4-6

weak

Cl^-

weak

Br^-

weak

F^-

weak

HSO₄^-

hydrogen sulfate ion

very weak

SO₄^2-

sulfate

very weak

NO₃^-

nitrate

ClO₄^-

very weak

H₂PO₄^-

dihyrdogen phosphate

pka = 7.21

very weak

HPO₄^2-

hydrogen phosphate

pka = 12.3

very weak

PO₄^3-

phosphate

very weak

NH₄⁺

ammonium

pka = 9.2

non-nucleophilic

lewis acids

non-nucleophilic

non-nucleophilic

non-nucleophilic

cations

Ex. Na⁺, Ca²⁺

non-nucleophilic