Naslov
A computational study of regioselectivity in ß- lactam iminothiazolidinone formation

Autori
Vazdar, Katarina ; Vazdar, Mario

Izvornik
Tetrahedron letters (0040-4039) 56 (2015); 6908-6911

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
iminothiazolidinones regioselectivity ; DFT calculations ; free energy barrier ; steric effects

Sažetak
Density functional theory calculations were performed to explain the different regioselectivity for the formation of β-lactam iminothiazolidinones. Computational results were in agreement with experimental observations that phenyl and cyclohexyl derivatives led to the thermodynamically more stable regioisomers formed by cyclization at the nitrogen atom directly attached to the β- lactam ring which was in contrast to the n- hexyl derivative where the regioisomer with the β-lactam ring attached to the imino bond is instead more stable. It was demonstrated that the different regioselectivity was the consequence of larger steric effects when bulky substituents and the leaving ethoxy group were in close contact during the cyclization step.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA