TY - JOUR
T1 - 1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuC≡CPh)
T2 - An inorganic version of a click reaction
AU - Del Castillo, Trevor J.
AU - Sarkar, Soumya
AU - Abboud, Khalil A.
AU - Veige, Adam S.
PY - 2011/8/2
Y1 - 2011/8/2
N2 - 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 Π-bonding HOMO orbital.
AB - 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 Π-bonding HOMO orbital.
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U2 - 10.1039/c1dt10787a
DO - 10.1039/c1dt10787a
M3 - Article
AN - SCOPUS:79961138279
SN - 1472-7773
VL - 40
SP - 8140
EP - 8144
JO - Journal of the Chemical Society. Dalton Transactions
JF - Journal of the Chemical Society. Dalton Transactions
IS - 32
ER -