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Lanthanide ion‐induced hydrolyses of alkyl esters and amides of α‐amino acids
Author(s) -
Takarada Tohru,
Takahashi Rei,
Yashiro Morio,
Komiyama Makoto
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199801)11:1<41::aid-poc969>3.0.co;2-3
Subject(s) - chemistry , lanthanide , hydrolysis , alkyl , medicinal chemistry , ion , catalysis , limiting , inorganic chemistry , organic chemistry , mechanical engineering , engineering
Abstract Lanthanide ion‐induced hydrolyses of methyl esters, ethyl esters, and amides of α‐amino acids were systematically studied. In the hydrolysis of the alkyl esters, all the lanthanide ions are effective and the catalytic activities decrease in the order Ce(III), Nd(III) > Sm(III) > Eu(III) > Gd(III), Ce(IV) > Pr(III) > Dy(III), Tb(III), Er(III), Ho(III), Tm(III) > La(III), Lu(III), Yb(III). For the hydrolysis of the amides, however, the Ce(IV) ion is overwhelmingly more active than other lanthanide(III) and non‐lanthanide ions. The results are interpreted in terms of the difference in the rate‐limiting step for these two reactions. © 1998 John Wiley & Sons, Ltd.