Bulletin of the Chemical Society of Japan p. 2917 - 2922 (1988)
Update date:2022-08-17
Topics:
Kinoshita, Tomomi
Shibayama, Koichi
Ikai, Keizo
Okamoto, Kunio
The salt effect of sodium phenoxide on the polarimetric (kp) and titrimetric rate constants (kt) has exhibited pattern B for the phenolysis of optically active 1-(p-methylphenyl)ethyl p-nitrobenzoate (ROPNB; (1)) in pure phenol.The other patterns A, C, and D were previously observed for the phenolyses of 1-phenylethyl p-nitrobenzoates with p-MeO- (2), p-H- (3), and p-NO2-substituents (4), respectively.Thus, the kp-kt pattern changes in the order A -> B -> C -> D as the stability of the intermediate decreases in the order of 2 > 1 > 3 > 4.All the kp-kt patterns can be correlated with the ion-pair stage for product formation, i.e., the pattern A with the second ion-pair intermediate and the patterns B, C, and D with the first one.The pattern of salt effect on the product distribution (percent of ROPh, o- and p-RC6H4OH, and p-MeC6H4CH=CH2) for 1 is also compatible with the kp-kt pattern B.
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