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Pregled bibliografske jedinice broj: 454274

Časopis

Autori: Ganguly, Bishwajit; Singh, Ajeet; Matković, Marija; Basarić, Nikola; Kesharwania, Manoj K.; Mlinarić-Majerski, Kata
Naslov: Hydrolysis and retro-aldol cleavage of ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate: competing reactions
Izvornik: Journal of physical organic chemistry (0894-3230) 24 (2011), 7; 578-587
Vrsta rada: članak
Ključne riječi: ester hydrolysis; retro-aldol; DFT; solvent effect; adamantane
Sažetak:
The hydrolysis of ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate (1) and the parent ester ethyl 3-hydroxybutyrate (4) has been studied experimentally and computationally. In the hydrolysis of threo-ester 1 with 2M NaOH, predominantly retro-aldol product was observed, whereas the hydrolyzed product was present in a minor amount. When the reaction is carried out under the same conditions with the parent ester ethyl 3-hydroxybutyrate (4), hydrolyzed product is exclusively observed. The competitive pathways, namely hydrolysis and the retro-aldol reaction for 1 and 4 were investigated using DFT calculations in the both gas and solvent phases. The calculated results at B3LYP/6-31+G* level revealed that the formation of retro-aldol products is kinetically and thermodynamically preferred over the hydrolysis of threo-ester 1 in the presence of a base. However, in methanol, the parent ester 4 showed that the retro-aldol process is less favored than the hydrolysis process. The bulky adamantyl group enhances the activation barriers for the hydrolysis of the ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate (1) through deleterious steric interaction with the nucleophile compared to parent ester ethyl 3- hydroxybutyrate (4).
Projekt / tema: 098-0982933-2911
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://onlinelibrary.wiley.com/doi/10.1002/poc.1793/abstract
Broj citata:
Altmetric:
DOI: DOI: 10.1002/poc.1793
URL cjelovitog teksta:
Google Scholar: Hydrolysis and retro-aldol cleavage of ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate: competing reactions
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 29. Ožu. 2010. u 09:40 sati



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