Archive for December 6th, 2009

The nature of the C≡S triple bond: part 3.

Sunday, December 6th, 2009

In the previous two posts, a strategy for tuning the nature of the CS bond in the molecule HO-S≡C-H was developed, based largely on the lone pair of electrons identified on the carbon atom. By replacing the HO group by one with greater σ-electron withdrawing propensity, the stereo-electronic effect between the O-S bond and the carbon lone pair was enhanced, and in the process, the SC bond was strengthened. It is time to do a control experiment in the other direction. Now, the HO-S group is replaced by a H2B-S group. The B-S bond, boron being very much less electronegative than oxygen, should be a very poor σ-acceptor. In addition, whereas oxygen was a π-electron donor (acting to strengthen the S=C region), boron is a π-acceptor, and will also act in the opposite direction. So now, this group should serve to weaken the S-C bond.

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