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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 (CC BY 3.0).
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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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