Naslov
Design of a depside with a lipophilic adamantane moiety : Synthesis, crystal structure and molecular conformation

Autori
Matković, Marija ; Veljković, Jelena ; Mlinarić-Majerski, Kata ; Molčanov, Krešimir ; Kojić-Prodić, Biserka

Izvornik
Journal of molecular structure (0022-2860) 832 (2007), 1/3; 191-198

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

Ključne riječi
depside design; adamantyl hydroxybutanoic acid; conformation; X-ray structure analysis

Sažetak
New adamantane depsides, ethyl 2-(1-adamantyl)-3-O-[(S)-Boc-Phe]butanoate (R, R, S)-1a and (S, S, S)-1b were prepared and characterized by spectroscopic data. The crystal structures and the stereochemistry of rac-(R, R, S)-1a and threo-2-(1-adamantyl)-3-hydroxy-butanoic acid rac-(R, R)-4a were determined by X-ray structure analysis. In the racemic crystal, the molecules of 1a from centrosymmetric dimers through hydrogen bonds involving a double acceptor function of the depside carbonil oxygen, and donors of the amino group and aromatic C-H atoms. The dimers are connected through an infinite chain of C-H...O interactions, were C-H is an aromatic donor and the ester carbonil oxygen is an acceptor. In the solid state, amphilic molecules 1a and 4a exihibit pronouced hydrophilic and hydropfobic biliayers.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA