Conformational chirality and chiral crystallization of N-sulfonylpyrimidine derivatives
| Autor: | Mladen Žinić, Tanja Kajfež Novak, Aleksandar Višnjevac, Marija Luić, Biserka Žinić, Dinko Žiher |
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| Rok vydání: | 2007 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Pyrimidine conformational chirality crystallization N-sulfonylpyrimidine Organic Chemistry Uracil Crystal structure Condensation reaction Biochemistry law.invention Thymine chemistry.chemical_compound Crystallography chemistry law Drug Discovery Crystallization Chirality (chemistry) |
| Zdroj: | Tetrahedron. 63:86-92 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2006.10.048 |
| Popis: | New N-sulfonylpyrimidine derivatives 1-(p-toluenesulfonyl)uracil (1), 1-(p-toluenesulfonyl)thymine (2), 5-bromo-1-(p-toluenesulfonyl)uracil (3), 1-(methanesulfonyl)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. |
| Databáze: | OpenAIRE |
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