Potassium tris(3,5-dimethyl-1-pyrazolyl)borate, abbreviated KTp*, is the potassium salt of the anion HB((CH3)2C3N2H)3. Tp*− is a tripodal ligand that binds to a metal in a facial manner, more specifically a Scorpionate ligand.[1] KTp* is a white crystalline solid that is soluble in polar solvents, including water and several alcohols.
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Names | |
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IUPAC name
Potassium tri(3,5-dimethyl-1-pyrazolyl)borohydride
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Other names
Tp* ligand
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.203.488 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C15H22BKN6 | |
Molar mass | 336.28 gmol−1 |
Appearance | White solid |
Melting point | 292 to 301 °C (558 to 574 °F; 565 to 574 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
editKTp* is synthesized in a manner similar to that of KTp by the reaction of potassium borohydride and 3,5-dimethylpyrazole. Hydrogen gas is evolved as each of the pyrazole reacts at the boron. The rate of B-N bond formation becomes more difficult with each successive 3,5-dimethylpyrazolyl due to the increase in steric hindrance around the boron:[2]
- 3 Me2C3N2H2 + KBH4 → KHB(Me2C3N2H)3 + 3 H2
The required dimethylpyrazole is obtained by condensation of hydrazine and acetylacetone.
Role as ligand
editThe active binding sites in Tp*− are the three nitrogen centers that are not bonded to the boron. Although more weakly binding than cyclopentadienyl ligands, Tp*− is still a tightly coordinating. The benefit of Tp*− over its sister compound Tp− is the addition of the methyl groups on the pyrazolyl rings, which increases the steric hindrance of the ligand enough that only one Tp*− can bind to a metal. This leaves the remaining coordination sites available for catalysis.[3]
References
edit- ^ Trofimenko, Swiatoslaw (1999). Scorpionates: Polypyrazolylborate Ligands and Their Coordination Chemistry. World Scientific. ISBN 978-1860941726.
- ^ Trofimenko, S. (2002). "Compounds of General Interest". Inorganic Syntheses. Inorganic Syntheses. Vol. 33. pp. 220–221. doi:10.1002/0471224502.ch4. ISBN 9780471208259.
- ^ Trofimenko, S (2004). "Scorpionates: genesis, milestones, prognosis". Polyhedron. 23 (2–3): 197–203. doi:10.1016/j.poly.2003.11.013.