1,3-Dipolar cycloaddition between a metal-azide (Ph3PAuN 3) and a metal-acetylide (Ph3PAuCCPh): An inorganic version of a click reaction

Trevor J. Del Castillo, Soumya Sarkar, Khalil A. Abboud, Adam S. Veige

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71 Scopus citations

Abstract

This report describes the synthesis and characterization of 1,5-bis-triphenylphosphinegold(i) 1,2,3-triazolate (3(1,5)). The synthesis of the dinuclear complex 3(1,5) is achieved via an unprecedented inorganic click (iClick) reaction between the metal-azide PPh 3AuN3 (1) and the metal-acetylide PPh3Au-CCPh (2). Characterization of 3(1,5) includes multinuclear NMR spectroscopy, combustion analysis, and single crystal X-ray crystallography. Experimental characterization is complemented with density-functional-theory (DFT) calculations which indicate the 1,4-isomer 3(1,4) is less stable by 3.3 kcal mol-1. The energetic difference lies primarily in the ability of the phenyl group in the 4-position of 3(1,5) to lie coplanar with the triazolate to create a delocalized π-bonding HOMO orbital.

Original languageEnglish (US)
Pages (from-to)8140-8144
Number of pages5
JournalDalton Transactions
Volume40
Issue number32
DOIs
StatePublished - Aug 28 2011
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

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