Tetraphenylmethane

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Tetraphenylmethane
Tetraphenylmethane.svg
Tetraphenylmethane-from-xtal-view-1-Mercury-3D-bs.png
Names
Preferred IUPAC name
1,1′,1′′,1′′′-Methanetetrayltetrabenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.132 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-144-0
PubChem CID
UNII
  • InChI=1S/C25H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H Yes check.svgY
    Key: PEQHIRFAKIASBK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C25H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
    Key: PEQHIRFAKIASBK-UHFFFAOYAS
  • c1ccccc1C(c2ccccc2)(c3ccccc3)c4ccccc4
Properties
C25H20
Molar mass 320.44 g/mol
Melting point 272 °C (522 °F; 545 K)
Structure [1]
tetragonal
P421c, No. 114
S4
a = 10.896 Å, c = 7.280 Å
(20 °C)
2
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg
Danger
H350
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tetraphenylmethane is an organic compound consisting of a methane core with four phenyl substituents. It was first synthesized by Moses Gomberg in 1898.

Contents

Synthesis

Gomberg's classical organic synthesis shown below starts by reacting triphenylmethyl bromide 1 with phenylhydrazine 2 to the hydrazine 3. Oxidation with nitrous acid then produces the azo compound 4 from which on heating above the melting point, nitrogen gas evolves with formation of tetraphenylmethane 5. [2]

Tetraphenylmethane full.svg

Gomberg was able to distinguish this compound from triphenylmethane (elemental analysis was not an option given the small differences in the hydrogen fractions of 6.29% and 6.60%) by nitration of 5 with nitric acid to 6. A strong base would be able to abstract the methine proton of the nitrated triphenylmethyl compound if present, forming a strongly colored compound.

He obtained further evidence for the formation of tetraphenylmethane by reducing the nitro groups to amino groups with zinc dust in acetic acid to the leuco dye 7, which on exposure to hydrochloric acid eliminates aniline to the known compound pararosaniline 8.

Gomberg's success in synthesizing tetraphenylmethane set him on the attempt to prepare the next homologue hexaphenylethane, which led him to the discovery of the triphenylmethyl radical.

See also

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Triphenylmethane Chemical compound

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

Adamantane Molecule with three connected cyclohexane rings arranged in the "armchair" configuration

Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond). It is a white solid with a camphor-like odor. It is the simplest diamondoid.

Moses Gomberg American chemist born in Russia

Moses Gomberg was a chemistry professor at the University of Michigan. He was elected to the National Academy of Sciences and served as president of the American Chemical Society.

Triphenylmethanol Chemical compound

Triphenylmethanol 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.

Triphenylmethyl radical Chemical compound

The triphenylmethyl radical (often shorted to trityl radical) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical ever to be described in organic chemistry. Because of its accessibility, the trityl radical has been heavily exploited.

Phenylboronic acid Chemical compound

Phenylboronic acid or benzeneboronic acid, abbreviated as PhB(OH)2 where Ph is the phenyl group C6H5-, is a boronic acid containing a phenyl substituent and two hydroxyl groups attached to boron. Phenylboronic acid is a white powder and is commonly used in organic synthesis. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.

Triphenylmethyl chloride Chemical compound

Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group.

<i>S</i>-Nitrosothiol

S-Nitrosothiols, also known as thionitrites, are organic compounds or functional groups containing a nitroso group attached to the sulfur atom of a thiol. S-Nitrosothiols have the general formula RSNO, where R denotes an organic group. Originally suggested by Ignarro to serve as intermediates in the action of organic nitrates, endogenous S-nitrosothiols were discovered by Stamler and colleagues and shown to represent a main source of NO bioactivity in vivo. More recently, S-nitrosothiols have been implicated as primary mediators of protein S-nitrosylation, the oxidative modification of cysteine thiol that provides ubiquitous regulation of protein function.

Triphenylmethyl hexafluorophosphate Chemical compound

Triphenylmethylhexafluorophosphate is an organic salt with the formula C
19
H
15
F
6
P
or (C
6
H
5
)
3
CPF
6
, consisting of the triphenylmethyl cation [(C
6
H
5
)
3
C]+
and the hexafluorophosphate anion [PF
6
]
.

Gombergs dimer Chemical compound

Gomberg's dimer is the organic compound with the formula Ph2C=C6H5-CPh3, where Ph = C6H5. It is a yellow solid that is air-stable for hours at room temperature and soluble in organic solvents. The compound achieved fame as the dimer of triphenylmethyl radical, which was prepared by Moses Gomberg in his quest for hexaphenylethane.

Thorium(IV) nitrate Chemical compound

Thorium(IV) nitrate is a chemical compound with the formula Th(NO3)4. A white solid in its anhydrous form, it can form tetra- and pentahydrates. As a salt of thorium it is weakly radioactive.

Triphenylcarbenium

In chemistry, triphenylcarbenium, triphenylmethyl cation, tritylium , or trityl cation is an ion with formula [C
19
H
15
]+
or (C
6
H
5
)
3
C+
, consisting of a carbon atom with a positive charge connected to three phenyl groups. It is a charged version of the triphenylmethyl radical (C
6
H
5
)
3
C
. The name is often abbreviated to triphenylmethyl or trityl in salts, although these names also denote the chemical group in compounds like triphenylmethyl chloride that do not contain the cation.

References

  1. Robbins, A.; Jeffrey, G. A.; Chesick, J. P.; Donohue, J.; Cotton, F. A.; Frenz, B. A.; Murillo, C. A. (1975-10-01). "A refinement of the crystal structure of tetraphenylmethane: three independent redeterminations". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 31 (10): 2395–2399. doi:10.1107/S0567740875007686. ISSN   0567-7408.
  2. Gomberg, M. (1898). "On tetraphenylmethane". J. Am. Chem. Soc. 20 (10): 773–780. doi:10.1021/ja02072a009.