What is tricyclohexylphosphine in organic chemistry?

Tricyclohexylphosphine is a tertiary phosphine with chemical formula C18H33P. It is also expressed with the formula P(C6H11)3 or P(Cy)3, where Cy stands for cyclohexyl group.

Tricyclohexylphosphine is formed by the substitution of three hydrogen atoms by three cyclohexyl group.

The molecular weight of Tricyclohexylphosphine is 280.43 g / mol and its melting point is 355K. Tricyclohexylphosphine is soluble in organic solvents.

Tricyclohexylphosphine is commonly used as a ligand in organometallic chemistry. It is characterized by both high basicity and a large ligand cone angle.

Why Is Tricyclohexylphosphine Highly Basic?

The phosphorous atom in tricyclohexylphosphine is sp3 hybridized. The phosphorous atom contains one lone pair of electron which can’t participate in resonance with cyclohexyl ring due to absent of pi bond in cyclohexyl ring.

Hence the lone pair on phosphorous atom is available for donation to the electron deficient groups, atoms or ions. Consequently tricyclohexylphosphine shows high basic character.

Use of tricyclohexylphosphine

The central phosphorous atom in tricyclohexylphosphine contains one lone pair of electron which is available for donation. Hence phosphorous atom can co-ordinate with the other electron deficient species by using its lone pair.

Due to such properties tricyclohexylphosphine is mainly used as a ligand in organometallic chemistry.