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. 2019 Feb 11;4(2):3000–3011. doi: 10.1021/acsomega.8b03521

Table 1. XPS Results for the Optimization of the Alkylation/Charge–Neutralization Reaction on 2, via Either the Sodium Salt (a–d) or the Protected Acid (e–h) of the Indicated Alkyl halides (See Figure S3).

reactant conversiona (%)
a sodium iodoacetate 87
b sodium bromoacetate 54
c sodium bromoethane sulfonate 74
d sodium bromopropane sulfonate 70
e tert-butyl iodoacetate + deprotection 85
f tert-butyl bromoacetate + deprotection 93
g methyl iodoacetate + deprotection 79
h methyl bromoacetate + deprotection 77
a

Based on conversion to quaternary amine as measured by XPS N 1s narrow scans.