Leaving groups ordered in decreasing ability to leave |
|
R–N2+ |
dinitrogen |
R–OR'2+ |
dialkyl ether |
R–OSO2R |
perfluoroalkylsulfonates (e.g. triflate) |
R–OTs, R–OMs, etc. |
tosylates, mesylates and similar sulfonates |
R–I |
iodide |
R–Br |
bromide |
R–OH2+, R'–OHR+ |
water, alcohols |
R–Cl |
chloride |
R–ONO2, R–OPO(OR')2 |
nitrate, phosphate, and other inorganic esters |
R–SR'2+ |
thioether |
R–NR'3+, R–NH3+ |
amines, ammonia |
R–F |
fluoride |
R–OCOR |
carboxylate |
R–OAr |
phenoxides |
R–OH, R–OR |
hydroxide |
R–N |
amides |
R–H |
hydride |
R–R' |
arenide, alkanide |