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Molecules 2008, 13(11), 2786-2795; doi:10.3390/molecules13112786
Article

Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone

1, 1, 2 and 3,*
1 Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P.O. Box 177, HR-10000 Zagreb, Croatia 2 Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia 3 Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, HR-10000 Zagreb, Croatia
* Author to whom correspondence should be addressed.
Received: 21 August 2008 / Revised: 26 September 2008 / Accepted: 13 October 2008 / Published: 6 November 2008
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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 α-(1-carbamyliminomethylene)-γ-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.
Keywords: 5-(2-Haloethyl)pyrimidine; Synthesis; X-ray crystal structure; Hydrogen bonds 5-(2-Haloethyl)pyrimidine; Synthesis; X-ray crystal structure; Hydrogen bonds
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Gazivoda, T.; Raić-Malić, S.; Hergold-Brundić, A.; Cetina, M. Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone. Molecules 2008, 13, 2786-2795.

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