Naslov
Conformational chirality and chiral crystallization of N-sulfonylpyrimidine derivatives

Autori
Višnjevac, Aleksandar ; Žinić, Mladen ; Luić, Marija ; Žiher, Dinko ; Kajfež Novak, Tanja ; Žinić, Biserka

Izvornik
Tetrahedron (0040-4020) 63 (2007), 1; 86-92

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

Ključne riječi
conformational chirality; crystallization; N-sulfonylpyrimidine

Sažetak
New N-sulfonylpyrimidine derivatives 1-(p-toluenesulfonyl)uracil (1), 1-(p-toluenesulfonyl)thymine (2), 5-bromo-1-(p-toluenesulfonyl)uracil (3), 1-(methylsulfonyl)uracil (4), 1-(1-naphthylsulfonyl)uracil (5) and 1-(1-naphthylsulfonyl)thymine (6) were prepared by the condensation reaction of silylated pyrimidine derivatives with selected sulfonyl chlorides in acetonitrile. Some members of the series showed unexpected crystal properties as a consequence of their conformational chirality in the solid state. Compounds 1 and 5 exhibited chiral crystallization, which was, in the case of 1, accompanied by the formation of racemically twinned crystals regardless of the solvent used, while 5 gave a conglomerate of enantiomorphous crystals. For 2, 3 and 6, substituents at the C-5 position of the pyrimidine ring prevented chiral crystallization by influencing the crystal packing. Analysis of the crystal structures of 1, 4, and 5, reveals the influence of the arylsulfonyl group on the occurrence or absence of chiral crystallization.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA