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,* email
Received: 21 August 2008; in revised form: 26 September 2008 / Accepted: 13 October 2008 / Published: 6 November 2008
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.
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
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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.

AMA 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(11):2786-2795.

Chicago/Turabian Style

Gazivoda, Tatjana; Raić-Malić, Silvana; Hergold-Brundić, Antonija; Cetina, Mario. 2008. "Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone." Molecules 13, no. 11: 2786-2795.

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