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ERIC Number: EJ1048345
Record Type: Journal
Publication Date: 2014-Dec
Pages: 4
Abstractor: As Provided
Reference Count: 8
ISSN: ISSN-0021-9584
Formation of an Oxidant-Sensible Pd(II) Coordination Compound and Its [superscript 1]H NMR Specific Characterization: A Preparative and Analytical Challenge in Current Coordination Chemistry
Abraham, Maria L.; Oppel, Iris M.
Journal of Chemical Education, v91 n12 p2174-2177 Dec 2014
A three-part experiment that leads to the synthesis of palladium(II) complex starting from a C[subscript 3]-symmetric triaminoguanidinium-based ligand is presented. In the first part, the preparation of tris-benzylidenetriaminoguanidinium chloride ([H[subscript 6]Br[subscript 3]L]Cl) by an acidic catalyzed 3-fold imine formation reaction of 5-bromo-2-hydroxybenzaldehyde and triaminoguanidinium chloride is described. Starting from the second part, the reaction procedures are performed under inert gas atmosphere. The conversion of PdCl[subscript 2] with acetonitrile to give [Pd(MeCN)[subscript 4]]Cl[subscript 2] as a precursor is performed at 80 °C. The third part of the experiment is a three-step procedure that begins with deprotonation of [H[subscript 6]Br[subscript 3]L]Cl, followed by transfer of [Pd(MeCN)[subscript 4]]Cl[subscript 2] to the reaction flask, where the chelation of Pd(II)-precursor leads to the in situ species [Pd(MeCN)H[subscript 3]Br[subscript 3]L]. Addition of PPh[subscript 3] as the final reaction step yields [Pd(PPh[subscript 3])H[subscript 3]Br[subscript 3]L]. This sequence of experiments provides an excellent example of ligand and transition metal preparation and its subsequent complexation to form an oxidant-sensitive organometallic species. Undergraduate students get the opportunity to learn Schlenk techniques and to investigate [superscript 1]H NMR spectra of organic and organometallic compounds starting from relatively simple to more advanced spectra. The distinct result of the chemical shift of the [superscript 4]J[subscript P-H]-affected doublet mirrors the preparative success of the student and demonstrates the utility of [superscript 1]H NMR experiments.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A