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Synthesis of Diazonium Tetrachloroaurate(III) Precursors for Surface Grafting
Department of Chemistry, Delaware State University, 1200 N. DuPont Highway, Dover, Delaware 19901, USA
Department of Chemistry, Center for Crystallographic Research, Michigan State University, East Lansing, Michigan 48824, USA
These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 8 November 2013; in revised form: 4 December 2013 / Accepted: 9 December 2013 / Published: 17 December 2013
Abstract: The synthesis of diazonium tetrachloroaurate(III) complexes [R-4-C6H4N≡N]AuCl4 involves protonation of anilines CN-4-C6H4NH2, C8F17-4-C6H4NH2, and C6H13-4-C6H4NH2 with tetrachloroauric acid H[AuCl4] 3H2O in acetonitrile followed by one-electron oxidation using [NO]PF6. FT-IR shows the diazonium stretching frequency at 2277 cm−1 (CN), 2305 cm−1 (C8F17), and 2253 cm−1 (C6H13). Thermogravimetric Analysis (TGA) shows the high stabilities of the electron-withdrawing substituents C8F17 and CN compared with the electron-donating substituent C6H13. Residual Gas Analysis (RGA) shows the release of molecular nitrogen as the main gas residue among other small molecular weight chlorinated hydrocarbons and chlorobenzene. Temperature-Dependent X-Ray Powder Diffraction (TD-XRD) shows the thermal decomposition in C6H13 diffraction patterns at low temperature of 80 °C which supports the TGA and RGA (TGA-MS) conclusions. X-ray structure shows N≡N bond distance of approximately 1.10 Å and N≡N-C bond angle of 178°.
Keywords: diazonium; tetrachloroaurate(III); X-ray
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Neal, S.N.; Orefuwa, S.A.; Overton, A.T.; Staples, R.J.; Mohamed, A.A. Synthesis of Diazonium Tetrachloroaurate(III) Precursors for Surface Grafting. Inorganics 2013, 1, 70-84.
Neal SN, Orefuwa SA, Overton AT, Staples RJ, Mohamed AA. Synthesis of Diazonium Tetrachloroaurate(III) Precursors for Surface Grafting. Inorganics. 2013; 1(1):70-84.
Neal, Sabine N.; Orefuwa, Samuel A.; Overton, Atiya T.; Staples, Richard J.; Mohamed, Ahmed A. 2013. "Synthesis of Diazonium Tetrachloroaurate(III) Precursors for Surface Grafting." Inorganics 1, no. 1: 70-84.