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Repair common Windows errors and clear accumulated junk for a smoother, more stable PC - no reinstall needed.Free scan · no reinstallMHPN, reported in 2017, was presented as the first superbase with two interacting phosphorus-ylide groups. Its two carbon atoms act as basicity centers, held close together by a naphthalene framework. The researchers measured strong solution basicity and investigated how a proton rapidly exchanges between the carbon centers after protonation.
What is a superbase?
A superbase is a substance with exceptionally strong proton-accepting ability. Basicity can be expressed in different ways, and the figures are meaningful only alongside their measurement conditions. For MHPN, the 2017 study reported an experimental pKBH+ value in acetonitrile and a separate calculated proton affinity in the gas phase; those are different quantities and should not be treated as interchangeable.
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What makes MHPN different from a classical proton sponge?
Classical proton sponges are nitrogen-centered bases: their basic sites are nitrogen atoms held in a geometry that supports proton acceptance. MHPN instead has two carbon basicity centers in phosphorus–carbon ylide groups. Its naphthalene scaffold brings those centers into proximity. The authors described it as the first superbase with two interacting P-ylide entities. The original 2017 paper investigated the structure and behavior using NMR spectroscopy, single-crystal X-ray diffraction, and theoretical calculations.
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1Scan for outdated or missing drivers - takes under a minute2Repair Windows errors before they cause bigger problems3Fix the driver behind crashes, sound loss and screen glitchesChemistry World characterized the discovery as a new class centred around carbon–phosphorus bonds. Its report also described a straightforward two-step synthesis, but the report is not a practical synthesis protocol; reagent quantities, yields, and handling details are not established by the available abstract. Katrina Krämer’s 2017 report provides that overview.
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How strong is the phosphorus bisylide superbase?
Kögel and colleagues reported an experimental pKBH+ of 33.3 ± 0.2 for MHPN on the acetonitrile scale in 2017. Separately, their theoretical calculation gave a gas-phase proton affinity of 277.9 kcal mol−1, nearly 15 kcal mol−1 above the corresponding monoylide in that computational comparison. The solution value and gas-phase calculation describe different settings, so neither should be substituted for the other or used as a universal ranking against every superbase. The 2017 study reports both figures.
How does the proton move between the carbon atoms?
After protonation, the proton rapidly exchanges between MHPN’s two basic carbon atoms. This is proton exchange, not evidence that the proton remains permanently centered between them. The researchers investigated the behavior experimentally and computationally; they proposed that this rapid exchange can partly account for the unexpectedly high basicity, rather than being its sole explanation.
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What did later phosphorus bisylide work find?
A 2025 follow-up study reported related superbases MTPN and P2-MHPN, with basicity values distinguished by solvent and method. The acetonitrile figures below are estimates in the authors’ abstract, not experimental measurements.
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| Compound | Experimental pKaH in THF | Estimated pKaH in acetonitrile | Proton self-exchange rate at 300 K |
|---|---|---|---|
| MTPN | 26.0 | 33.6 | 2298 s−1 |
| P2-MHPN | 29.5 | 37.4 | 300 s−1 |
These are values reported by the 2025 follow-up authors. They should not be directly ranked against MHPN’s 2017 pKBH+ on the acetonitrile scale without accounting for the different compounds and reported measures. Nor are the estimated acetonitrile values the same kind of evidence as the experimental THF values. The 2025 paper’s PubMed record summarizes the follow-up findings.
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What the discovery established—and what remained a prospect
The 2017 work established MHPN as a phosphorus bisylide superbase with two interacting carbon basicity centers and investigated its structural and proton-exchange behavior. Chemistry World also reported that the authors considered adding phosphazene groups as a way to increase superbasicity. That was a research prospect reported in 2017, not an established result; the later evidence described here concerns the specifically reported MTPN and P2-MHPN compounds.
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