title: Synthesis and structural characterization of the 5-(2-haloethyl)pyrimidines--hydrogen-bonded chains in alpha-(1-carbamyliminomethylene)-gamma-butyrolactone.
abstract: Three novel 5-(2-haloethyl)pyrimidine derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, MS, IR spectra and elemental analysis. Iodine and chlorine atoms in the C-5 side chain were introduced by reaction of 5-(2-hydroxyethyl)pyrimidine with hydroiodic acid and phosphoryl chloride, respectively. The structure of the intermediate alpha-(1-carbamyliminomethylene)-gamma-butyrolactone was determined by X-ray crystal structure analysis. The molecule deviates very slightly from planarity. Three N-H...O hydrogen bonds link the molecules into one-dimensional chains of edge-fused rings.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Zagreb, Croatia.
authors.forename: Tatjana
authors.initials: T
authors.lastname: Gazivoda
authors.forename: Silvana
authors.initials: S
authors.lastname: Raić-Malić
authors.forename: Antonija
authors.initials: A
authors.lastname: Hergold-Brundić
authors.forename: Mario
authors.initials: M
authors.lastname: Cetina
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013057:Spectrum Analysis
chemical_list: D011743:Pyrimidines; C534555:alpha-(1-carbamyliminomethylene)-gamma-butyrolactone; D015107:4-Butyrolactone