# Does triphenylphosphine show resonance?

The lone pair of phosphorus and the double bonds in benzene looks to be in conjugation. Do the molecule show resonance? If so, how?

• The final arbiter will probably be some computational study, but phosphorus 3p overlap with carbon 2p is not great to begin with. – orthocresol Apr 6 '17 at 17:15
• Somewhat related, since the lone pair of the $\ce{P}$ atom is addressed: chemistry.stackexchange.com/questions/38599 – Klaus-Dieter Warzecha Apr 6 '17 at 17:36
• @orthocresol,What do you think about the answer below? – Kai Hiwatari Apr 6 '17 at 18:01
• There's probably no question that some degree of resonance exists; and indeed it's not possible for donation into all 3 rings to happen at once. However, the devil is in the details: how much of it is there? I personally don't know, but I don't think it's a lot, at least simply based on overlap arguments. – orthocresol Apr 6 '17 at 18:31