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Triphenylmethanol
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Triphenylmethanol
Triphenylmethanol (also known as triphenylcarbinol and TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.
Triphenylmethanol features three phenyl (Ph) rings and an alcohol group bound to a central tetrahedral carbon atom. All three C–Ph bonds are typical of sp3-sp2 carbon-carbon bonds with lengths of approximately 1.47 Å, while the C–O bond length is approximately 1.42 Å.
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride:
The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.
As a derivative of methanol, triphenylmethanol is expected to have a pKa in the range of 16–19. Typical of alcohols, resonance offers no stabilization of the conjugate base due to being bonded to a sp3 carbon atom. Stabilization of the anion by solvation forces is largely ineffective due to the steric influence of the three phenyl groups.
The basicity of triphenylmethanol is enhanced due to the formation of a resonance-stabilized carbocation upon breaking of the C–O bond. After protonation of the oxygen under strongly acidic conditions, triphenylmethanol loses water to form the triphenylmethyl ("trityl") cation:
The trityl cation is one of the easiest carbocations to isolate, although it quickly reacts with water.
Triphenylmethyl hydroperoxide is prepared from by treating triphenylmethanol with hydrogen peroxide in the presence of acid:
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Triphenylmethanol
Triphenylmethanol (also known as triphenylcarbinol and TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.
Triphenylmethanol features three phenyl (Ph) rings and an alcohol group bound to a central tetrahedral carbon atom. All three C–Ph bonds are typical of sp3-sp2 carbon-carbon bonds with lengths of approximately 1.47 Å, while the C–O bond length is approximately 1.42 Å.
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride:
The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.
As a derivative of methanol, triphenylmethanol is expected to have a pKa in the range of 16–19. Typical of alcohols, resonance offers no stabilization of the conjugate base due to being bonded to a sp3 carbon atom. Stabilization of the anion by solvation forces is largely ineffective due to the steric influence of the three phenyl groups.
The basicity of triphenylmethanol is enhanced due to the formation of a resonance-stabilized carbocation upon breaking of the C–O bond. After protonation of the oxygen under strongly acidic conditions, triphenylmethanol loses water to form the triphenylmethyl ("trityl") cation:
The trityl cation is one of the easiest carbocations to isolate, although it quickly reacts with water.
Triphenylmethyl hydroperoxide is prepared from by treating triphenylmethanol with hydrogen peroxide in the presence of acid:
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