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. Author manuscript; available in PMC: 2023 Apr 15.
Published in final edited form as: J Org Chem. 2022 Mar 30;87(8):5076–5084. doi: 10.1021/acs.joc.1c02931

Table 2.

Photolysis (5 mW LED at 365 nm) of alkyl-Cbls in DMF.

ß-axial Substituent K OW a k (s−1)b Φc
4 ethyl 1.33 0.14 ± 0.02 0.46 ± 0.08
7 decyl 4.67 0.09 ± 0.02 0.29 ± 0.05
8 cyclopropyl 1.25 0.057 ± 0.009 0.19 ± 0.03
12 cyclohexylmethyl 2.83 0.12 ± 0.01 0.40 ± 0.01
15 1-amino-1-carboxypropyl −0.41 0.036 ± 0.005 0.12 ± 0.02
a

The octanol water partition coefficient was calculated using ChemDraw 20.0.

b

Initial rate of photolysis from the average of three photolysis trials per conjugate.

c

The quantum yields were calculated using methyl-Cbl as the actinometer.38