Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triphenylmethanol: Difference between pages

| Watchedfields = changed

| verifiedrevid = 470616817

| Name = Triphenylmethanol

| ImageFile1 = Triphenylmethanol.png

| ImageFile2 = Triphenylmethanol crystals.jpg

| ImageName1 = Triphenylmethanol crystals

| PIN = Triphenylmethanol

| OtherNames = Triphenylcarbinol<br />Tritanol

| Section1 = {{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 6215

|PubChem = 6457

|InChI = 1/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H

|InChIKey = LZTRCELOJRDYMQ-UHFFFAOYAJ

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 118166

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = LZTRCELOJRDYMQ-UHFFFAOYSA-N

|CASNo = 76-84-6

|CASNo_Ref = {{cascite|correct|CAS}}

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = U97Q0OU9KB

|SMILES = OC(c1ccccc1)(c2ccccc2)c3ccccc3

| Section2 = {{Chembox Properties

|Formula = C₁₉H₁₆O

|MolarMass = 260.33 g/mol

| Appearance = White crystalline solid

|Density = 1.199 g/cm³

|MeltingPtC = 160 to 163

|BoilingPtC = 360 to 380

|MagSus = -175.7·10⁻⁶ cm³/mol }}

| Section7 = {{Chembox Hazards

|ExternalSDS = [http://www.coleparmer.com/Assets/Msds/45870.htm External MSDS]}}

| Section8 = {{Chembox Related

|OtherCompounds = [[Triphenylmethane]], [[Tricyclohexylmethanol]]}}

'''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.<ref name=Ull/>

== History ==

After the German chemist [[August Kekulé]] and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) first synthesized [[triphenylmethane]] in 1872,<ref>Aug. Kekulé and A. Franchimont (1872) [https://babel.hathitrust.org/cgi/pt?id=uc1.b3481750;view=1up;seq=868 "Ueber das Triphenylmethan"] (On triphenylmethane), ''Berichte der deutschen chemischen Gesellschaft'', '''5''' : 906-908.</ref> the Russian doctoral student Walerius Hemilian (1851–1914) first synthesized triphenylmethanol in 1874 by reacting triphenylmethyl bromide with water as well as by oxidizing triphenylmethane.<ref>W. Hemilian (1874) [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025694776;view=1up;seq=253 "Synthese des Triphenylmethans und des Methyl-phenyl-diphenylmethans"] (Synthesis of triphenylmethane and of methyl-phenyl-diphenylmethane), ''Berichte der deutschen chemischen Gesellschaft'', '''7''' : 1203–1210 ; see pp. 1206–1207.</ref>

==Structure and properties==

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 ''sp''³-''sp''² carbon-carbon bonds with lengths of approximately 1.47 [[angstrom|Å]], while the C–O bond length is approximately 1.42 [[angstrom|Å]].<ref>{{cite journal |doi=10.1107/S2053229619010714|title=Deciphering the Hydrogen-Bonding Scheme in the Crystal Structure of Triphenylmethanol: A Tribute to George Ferguson and Co-workers|year=2019|last1=Rodríguez Tzompantzi|first1=Tomasa|last2=Amaro Hernández|first2=Aldo Guillermo|last3=Meza-León|first3=Rosa Luisa|last4=Bernès|first4=Sylvain|journal=Acta Crystallographica Section C: Structural Chemistry|volume=75|issue=9|pages=1266–1273|pmid=31484815|pmc=6727172|bibcode=2019AcCrC..75.1266R }}</ref>

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]]:<ref>{{OrgSynth | author = W. E. Bachmann | title = Triphenylchloromethane | volume = 23 | lpages = 100 | doi = 10.15227/orgsyn.023.0100}}</ref>

:Ph₃COH + MeCOCl → Ph₃CCl + MeCO₂H

The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable [[hydroperoxide]], Ph₃COOH.<ref>Bryant E. Rossiter and Michael O. Frederick "Triphenylmethyl Hydroperoxide" E-EROS Encyclopedia of Reagents for Organic Synthesis, 2013. {{doi|10.1002/047084289X.rt363m.pub2}}</ref>

===Acid-base properties===

As a derivative of [[methanol]], triphenylmethanol is expected to have a p''K''_a in the range of 16-19. Typical of [[Alcohol (chemistry)|alcohol]]s, resonance offers no stabilization of the conjugate base due to being bonded to a saturated 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:

:Ph₃COH + H⁺ → Ph₃C⁺ + H₂O

The [[trityl cation]] is one of the easiest [[carbocation]]s to isolate, although it quickly reacts with water.

==Synthesis==

The preparation of triphenylmethanol from [[methyl benzoate]] or [[benzophenone]] and [[phenylmagnesium bromide]] is a common laboratory experiment for illustrating the [[Grignard reaction]].<ref>{{OrgSynth | author = W. E. Bachmann and H. P. Hetzner | title = Triphenylcarbinol | collvol = 3 | collvolpages = 839 | prep = cv3p0839}}</ref> An alternative starting material is [[diethyl carbonate]].<ref>{{cite journal | title = The GC–MS Observation of Intermediates in a Stepwise Grignard Addition Reaction | author = Latimer, Devin | journal = [[J. Chem. Educ.]] | year = 2007 | volume = 84 | pages = 699 | doi = 10.1021/ed084p699 | issue = 4| bibcode = 2007JChEd..84..699L}}</ref>

:[[File:Synthesis of triphenylmethanol.png|500px|Synthesis of triphenylmethanol]]

==Applications==

Although not of major industrial importance, triphenylmethanol is a useful reagent in the research laboratory. Substituted derivatives of triphenylmethanol are intermediates in the production of the commercially useful [[triarylmethane dye]]s.<ref name=Ull>{{Ullmann's | last1 = Gessner | first1 = Thomas | last2 = Mayer | first2 = Udo | title = Triarylmethane and Diarylmethane Dyes | year = 2000 | doi = 10.1002/14356007.a27_179}}</ref>

==References==

{{reflist}}

[[Category:Tertiary alcohols]]

[[Category:Phenyl compounds]]

[[Category:Substances discovered in the 19th century]]