Trevor J. Del Castillo, Soumya Sarkar, Khalil A. Abboud and Adam S. Veige, 1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuCCPh): an inorganic version of a click reaction
Dalton Transactions, 2011-05-04
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 PPh3AuN3 (1) and the metal–acetylide PPh3Au–C CPh (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 p-bonding HOMO orbital.