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. Author manuscript; available in PMC: 2014 Apr 5.
Published in final edited form as: Org Lett. 2013 Mar 11;15(7):1646–1649. doi: 10.1021/ol400427x

Table 2.

Apparent 2nd order rate constants (M 1 min 1) for different ortho proton donor nucleophilic catalysts.a

catalyst 2nd order rate constant rel. to uncat. rxn.
(none) 0.10 ± 0.01 1
graphic file with name nihms455047t1.jpg 1.1 ± 0.1 11
graphic file with name nihms455047t2.jpg 4.7 ± 0.3 46
graphic file with name nihms455047t3.jpg 5.0 ± 0.7 49
graphic file with name nihms455047t4.jpg 8.5 ± 0.5 83
graphic file with name nihms455047t5.jpg 5.4 ± 0.7 53
a

Conditions: 18 µM NBD Hydrazine, 1 mM 4-nitrobenzaldehyde, 1 mM catalyst in 10:1 PBS (pH 7.4):DMF, 23 °C.