Aggregation of Hydrogen Bonded Dimeric Tri-Organotin Amino Substituted Pyrimidine-2-Thiolates

Anastasia Ioannidou; Agnieszka Czapik; Petros Gkizis; Muhamad Perviaz; Dimitrios Tzimopoulos; Maria Gdaniec; Pericles D. Akrivos

doi:10.1071/CH12537

RESEARCH ARTICLE

Aggregation of Hydrogen Bonded Dimeric Tri-Organotin Amino Substituted Pyrimidine-2-Thiolates

Anastasia Ioannidou ^A , Agnieszka Czapik ^B , Petros Gkizis ^A , Muhamad Perviaz ^C , Dimitrios Tzimopoulos ^A ^D , Maria Gdaniec ^B ^D and Pericles D. Akrivos ^A

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Aristotle University, 541 24 Thessaloniki, Greece.

^B Faculty of Chemistry, Adam Mickiewicz University, 70 580 Poznań, Poland.

^C Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, 75270 Karachi, Pakistan.

^D Corresponding authors. Email: dtzimopo@pharm.auth.gr; magdan@amu.edu.pl

Australian Journal of Chemistry 66(5) 600-606 https://doi.org/10.1071/CH12537
Submitted: 7 December 2012 Accepted: 30 January 2013 Published: 7 March 2013

Abstract

The synthesis of six tri-organotin compounds with 4-amino and 4,6-diaminopyrimidine-2-thiolate is described. The compounds have the general formula R₃Sn(thiolate) where R = Me, Bu, or Ph. The compounds are investigated by a variety of spectroscopic techniques both in solution and in the solid state. The environment around the tin centres proves to be tetrahedral with monodentate thiolate anions as is inferred from the infrared and NMR spectra. The coordination sphere is not affected even by the presence of DMSO as solvent. In the solid state, the crystal structure determination of the trimethyl and triphenyltin derivatives of the 4,6-diaminopyrimidine-2-thiolate ligand, reveal an association into centrosymmetric dimers through N–H⋯N hydrogen-bonding interactions leaving the organotin site practically unaffected. However, in addition to the classical hydrogen bonding, weaker N–H⋯RS and N–H⋯Rπ interactions are also present and play an important role in determining further aggregation of these dimers which gives rise to a three-dimensional polymeric structure in the case of the trimethyltin and a layer of dimers in the case of the triphenyltin derivative, respectively.

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Aggregation of Hydrogen Bonded Dimeric Tri-Organotin Amino Substituted Pyrimidine-2-Thiolates

Abstract

References

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