Skip to main content
. Author manuscript; available in PMC: 2014 Mar 1.
Published in final edited form as: Org Lett. 2013 Feb 14;15(5):1084–1087. doi: 10.1021/ol400054m

Table 2.

Rate Constants of Hydrolysisa

graphic file with name nihms446619u4.jpg
entry R = khyd in D2O khyd in bufferb
1a H NDc NDc
1b 3-F 2.3 ± 0.2 × 10−5 7.1 ± 0.3 × 10−5
1c 5-F NDc NDc
1d 5-CF3 1.10 ± 0.05 × 10−6 7.0 ± 0.5 × 10−5
1e 6-CF3 NDc 1.20 ± 0.06 x10−4
1f 5-NO2 6.4 ± 0.4 × 10−5 2.40 ± 0.07 × 10−3
1g 4-CN 1.40 ± 0.03 × 10−6 1.60 ± 0.04 × 10−4
1h 5-CN 1.40 ± 0.05 × 10−5 8.3 ± 0.2 × 10−4
1i 6-CN 4.1 ± 0.3 × 10−6 4.10 ± 0.04 × 10−4
a

Rate constants given in units of min−1 were determined by 1H NMR spectroscopy.

b

50 mM phosphate buffer pH = 7.2.

c

Not determined, the reaction was too slow to observe hydrolysis.