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. Author manuscript; available in PMC: 2010 Feb 1.
Published in final edited form as: J Adhes. 2009 Feb 1;85(2-3):126. doi: 10.1080/00218460902782188

Table 1.

Effect of Chlorination on the pKa of the o-Dihydroxyl Groups in DOPA (pKa was Calculated using www.chemaxon.com/demosite/marvin/index.html)

pK1 pK2
DOPA 12.50 (4-OH) 8.74 (3-OH)
6-Cl-4,5-DOPA 12.05 (4-OH) 7.82 (3-OH)
3-Cl-4,5-DOPA 7.85 (4-OH) 12.01 (5-OH)
2-Cl-4,5-DOPA 8.32 (4-OH) 12.15 (5-OH)