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. 2008 Nov 6;13(11):2786-95.
doi: 10.3390/molecules13112786.

Synthesis and structural characterization of the 5-(2-haloethyl)pyrimidines--hydrogen-bonded chains in alpha-(1-carbamyliminomethylene)-gamma-butyrolactone

Tatjana Gazivoda  1 , Silvana Raić-Malić, Antonija Hergold-Brundić, Mario Cetina
Affiliations

Synthesis and structural characterization of the 5-(2-haloethyl)pyrimidines--hydrogen-bonded chains in alpha-(1-carbamyliminomethylene)-gamma-butyrolactone

Tatjana Gazivoda et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Synthesis of the 5-(2-haloethyl)pyrimidines 4-6.
Figure 1
Figure 1
A molecular structure of 2, with the atom-numbering scheme. Displacement ellipsoids for nonhydrogen atoms are drawn at the 40 % probability level.
Figure 2
Figure 2
Fragments from a Cambridge Structural Database survey.
Figure 3
Figure 3
A crystal packing diagram of 2, viewed along the a axis, showing chains of edge-fused rings formed by N−H···O hydrogen bonds.
Figure 4
Figure 4
A crystal packing diagram of 2, viewed along the b axis, showing parallel chains of hydrogen-bonding molecules.
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