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. Author manuscript; available in PMC: 2024 Feb 17.
Published in final edited form as: J Org Chem. 2023 Feb 6;88(4):2089–2094. doi: 10.1021/acs.joc.2c02420

Table 1.

QMA equilibration and elution solution investigation

QMA Equilibration
Agent
76/77Br Trapping (%) Entry QMA Elution
Agent
pKaa 76/77Br
Eluted (%)
n
Na2SO4 (0.5 M) 96 ± 4 %
n = 11
1 NH4OH 9.23 93 ± 7 9
2 Me3N 9.8 99 1
3 MeNH2 10.66 98 1
4 Me2NH 10.73 100 1
5 DBU 13.5 99 1
NaHCO3 (0.5 M) 99 ± 0.5 %
n = 9
6 NH4OH 9.23 1 1
7 Me3N 9.8 5 ± 1 2
8 MeNH2 10.66 55 1
9 Me2NH 10.73 86 ± 18 8
10 Me2NHb 10.73 94 ± 6 6
11 DBU 13.5 100 1
a

pKa values in aqueous solution from CRC Handbook of Chemistry and Physics Online except DBU from Kaupmees et al. Croat. Chem. Acta 87(4): 385–395 (2014).

b

Eluted with 1.6 mL of QMA releasing agent instead of the standard 800 μL. 0.1 M 1:1 MeCN / H2O