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The effect of the binding modes of two amino terminal groups present on two gold protrusions on currents passing through a single molecular junction of Au/1,4-diaminobutane/Au was studied via the repeated formation of a break junction using a scanning tunneling microscope (STM) under nitrogen at room temperature. In addition to the two reported (high and low) values of the single molecular conductance of diaminobutane, another lower conductance was found through a careful analysis of histograms in a low-current range (0–0.3 nA). The techniques used here to improve the determination of the values of single molecular conductance were the selection of valid i–s curves with current steps and the use of the robust statistical method to correct for the contribution of the background tunneling currents to the current histograms. These three single molecular conductance values are attributed to three different binding modes of the two terminal amino groups giving the three different contact resistances at room temperature. That is, each amino terminal group is likely to be bound to one or the other gold protrusion through a more or a less conductive contact mode. Thus, a single molecular junction between two gold electrodes has three different contact modes, i.e., i) more–more, ii) more–less (or less–more), and iii) less–less conductive contact modes at the two ends.

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A practical and highly effective one-pot synthesis of versatile heteroaryl ketones directly from carboxylic acids and heteroaryl halides under mild conditions is reported. This method does not require derivatization of carboxylic acids (preparation of acid chlorides, Weinreb amides, etc.) or the use of any additives/catalysts. A wide substrate scope of carboxylic acids with high functional group tolerance has also been demonstrated. The results reveal that the presence of an α-nitrogen on the halide substrate greatly improves the desired ketone formation.

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