# Is phosphorine (C₅H₅P) aromatic?

Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?

• Phosphinine is aromatic, but somewhat less than benzene. – mykhal Nov 23 '18 at 16:23

## 1 Answer

Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.

• With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book. – Martin - マーチン Dec 4 '18 at 16:38
• So ... you apparently think this is not aromatic? – Oscar Lanzi Dec 5 '18 at 0:38
• No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about. – Martin - マーチン Dec 5 '18 at 9:22