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The Sterically Mediated Reaction of Some Triorganotins with Picolinic Acid N-Oxide

Undergraduate #43
Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)

Adewola Osunsade - University of the District of Columbia
Co-Author(s): Xueqing Song, University of the District of Columbia, Washington, DC



Previous work in our laboratory examined the preferred mechanism in the reaction of Triphenyltin Hydroxide with Picolinic Acid N-Oxide. In this case, the tin had the option of either bonding covalently with the oxygen from the acid’s deprotonated carboxyl group via a substitution mechanism to form a 4-coordinated product, or coordinating with the oxygen from the N-Oxide of the ligand via an addition mechanism. We were able to show that both mechanisms were observed, and the product formed was a loosely associated 5-coordinated polymer that dissociated in solution into the substitution product. We hypothesize that this reaction is sterically mediated, and that the extent of association seen in the polymer – or whether a polymer forms at all – is dependent on the size of the organic groups bonded to the tin atom. We predict smaller R groups will result in a chain of tightly bound monomer units, while larger ones will form a more weakly linked product. A better understanding of the preferred reaction pathways of various triorganotins will increase the ease with which they can be functionalized in order to enhance their innate biocidal activity.

Picolinic Acid N-Oxide was reacted with a series of triorganotin chlorides (R = Pr, Bu, Cy, Ph, and Bn) in a 1:1 molar ratio in the presence of 1 molar equivalent of either triethylamine or dicyclohexylamine; the resulting products were purified. Characterization by FT-IR and NMR spectroscopies is underway. Preliminary data suggest the tripropyl- and tributyl-tin products in this case exist as liquids, while the triphenyltin complex is solid. The tribenzyltin complex is still being characterized, while the tricyclohexyltin reaction seems unlikely to proceed. X-ray crystallographic results will be discussed. Thorough structural analysis of our complexes will allow us to confirm or refute the validity of our hypothesis.

As the toxicity of triorganotins against a particular species is thought to be dependent on the R groups on the tin, this series will also be screened against different species of bacteria.

Funder Acknowledgement(s): Financial support from the Science, Technology, Engineering and Mathematics (STEM) Program at UDC is gratefully acknowledged (NSF/HBCU-UP-HRD-0928444).

Faculty Advisor: Xueqing Song,

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This material is based upon work supported by the National Science Foundation (NSF) under Grant No. DUE-1930047. Any opinions, findings, interpretations, conclusions or recommendations expressed in this material are those of its authors and do not represent the views of the AAAS Board of Directors, the Council of AAAS, AAAS’ membership or the National Science Foundation.

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