page_title: Diphosphagermylene
hierarchical_section_title: Diphosphagermylene
caption_attribution_description: English: Diphosphagermylene
context_page_description: Diphosphagermylenes are a class of compounds containing a divalent germanium atom bound to two phosphorus atoms. While these compounds resemble diamidocarbenes, such as N-heterocyclic carbenes, diphosphagermylenes display bonding characteristics distinct from those of diamidocarbenes. In contrast to NHC compounds, in which there is effective N-C p-p overlap between the lone pairs of planar nitrogens and an empty p-orbital of a carbene, systems containing P-Ge p-p overlap are rare. Until 2014, the geometry of phosphorus atoms in all previously reported diphosphatetrylenes are pyramidal, with minimal P-Ge p-p interaction. It has been suggested that the lack of p-p in Ge-P bonds is due to the high energetic barrier associated with achieving a planar configuration at phosphorus, which would allow for efficient p-p overlap between the phosphorus lone pair and the empty P orbital of Ge. The resulting lack of π stabilization contributes to the difficulty associated with isolating diphosphagermylene and the Ge-P double bonds.
context_section_description: Diphosphagermylenes are a class of compounds containing a divalent germanium atom bound to two phosphorus atoms. While these compounds resemble diamidocarbenes, such as N-heterocyclic carbenes (NHC), diphosphagermylenes display bonding characteristics distinct from those of diamidocarbenes. In contrast to NHC compounds, in which there is effective N-C p(π)-p(π) overlap between the lone pairs of planar nitrogens and an empty p-orbital of a carbene, systems containing P-Ge p(π)-p(π) overlap are rare. Until 2014, the geometry of phosphorus atoms in all previously reported diphosphatetrylenes are pyramidal, with minimal P-Ge p(π)-p(π) interaction. It has been suggested that the lack of p(π)-p(π) in Ge-P bonds is due to the high energetic barrier associated with achieving a planar configuration at phosphorus, which would allow for efficient p(π)-p(π) overlap between the phosphorus lone pair and the empty P orbital of Ge. The resulting lack of π stabilization contributes to the difficulty associated with isolating diphosphagermylene  and the Ge-P double bonds. However, utilization of sterically encumbering phosphorus centers has allowed for the isolation of diphosphagermylenes with a planar phosphorus center with a significant P-Ge p(π)-p(π) interaction.
caption: Diphosphagermylene.
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