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Triphenylcarbenium
Jorge Stolfi: /* top */ typo
[[File:Triphenylcarbenium.png|right|thumb|Triphenylcarbenium]]
In [[chemistry]], '''triphenylcarbenium''', '''triphenylmethyl cation''', or '''trityl cation''' is an [[ion]] with formula or , consisting of a [[carbon]] atom with a [[electric charge|positive charge]] connected to three [[phenyl]] groups. It is a charged version of the [[triphenylmethyl radical]] <sup>•</sup>. The name is often abbreviated to '''triphenylmethyl''' or '''trityl''' in salts, alhough these names also denote the chemical group in compounds like [[triphenylmethyl chloride]] that do not contain the cation.
Triphenylcarbenium is a relatively stable [[carbenium]] ion, because the positive charge can be distributed among 10 of the carbon atoms (the 3 carbon atoms in the ''ortho'' and ''para'' positions of each of the three phenyl groups, plus the central carbon atom).<ref name=deno/><ref name=Urch/> The cation exists in important chemical [[reagent]]s and [[catalyst]]s such as
* [[triphenylmethyl hexafluorophosphate]]
* [[triphenylmethyl tetrafluoroborate]]
* [[triphenylmethyl perchlorate]]
This and other similar cations can be obtained as intensely colored solutions by dissolving [[aryl]]-substituted [[methanol]]s in concentrated [[sulfuric acid]].<ref name=deno/>
==Triarylmethane dyes==
[[Triarylmethane dye]]s are derivatives are stabilized version of the trityl cation. They are water-soluble and are often obtained as the chloride salts. These dyes have strong electron donor groups, often amines, at the ''p''-positions of two or three of the aryl groups.<ref>Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in [[Ullmann's Encyclopedia of Industrial Chemistry]] 2002, [[Wiley-VCH]], Weinheim.</ref>
<gallery caption="Triarylmethane dyes" widths="180px" heights="120px" perrow="3">
Image:Methyl Violet 10B.png|[[Crystal violet]].
Image:NewFuchsineStructure.png|[[New fuchsine]] dye.
File:Pararosaniline.png|[[Pararosaniline]]
</gallery>
==See also==
*[[Triphenylmethane]]
*[[Triphenylmethanol]]
==References==
<references>
<ref name=deno>N. C. Deno, J. J. Jaruzelski, and Alan Schriesheim (1955) "Carbonium ions. I. An acidity function (''C''<sub>0</sub>) derived from arylcarbonium ion equilibria." ''Journal of the American Chemical Society'', voume 77, issue 11, pages 3044–3051. </ref>
<ref name=Urch></ref>
</references>
In [[chemistry]], '''triphenylcarbenium''', '''triphenylmethyl cation''', or '''trityl cation''' is an [[ion]] with formula or , consisting of a [[carbon]] atom with a [[electric charge|positive charge]] connected to three [[phenyl]] groups. It is a charged version of the [[triphenylmethyl radical]] <sup>•</sup>. The name is often abbreviated to '''triphenylmethyl''' or '''trityl''' in salts, alhough these names also denote the chemical group in compounds like [[triphenylmethyl chloride]] that do not contain the cation.
Triphenylcarbenium is a relatively stable [[carbenium]] ion, because the positive charge can be distributed among 10 of the carbon atoms (the 3 carbon atoms in the ''ortho'' and ''para'' positions of each of the three phenyl groups, plus the central carbon atom).<ref name=deno/><ref name=Urch/> The cation exists in important chemical [[reagent]]s and [[catalyst]]s such as
* [[triphenylmethyl hexafluorophosphate]]
* [[triphenylmethyl tetrafluoroborate]]
* [[triphenylmethyl perchlorate]]
This and other similar cations can be obtained as intensely colored solutions by dissolving [[aryl]]-substituted [[methanol]]s in concentrated [[sulfuric acid]].<ref name=deno/>
==Triarylmethane dyes==
[[Triarylmethane dye]]s are derivatives are stabilized version of the trityl cation. They are water-soluble and are often obtained as the chloride salts. These dyes have strong electron donor groups, often amines, at the ''p''-positions of two or three of the aryl groups.<ref>Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in [[Ullmann's Encyclopedia of Industrial Chemistry]] 2002, [[Wiley-VCH]], Weinheim.</ref>
<gallery caption="Triarylmethane dyes" widths="180px" heights="120px" perrow="3">
Image:Methyl Violet 10B.png|[[Crystal violet]].
Image:NewFuchsineStructure.png|[[New fuchsine]] dye.
File:Pararosaniline.png|[[Pararosaniline]]
</gallery>
==See also==
*[[Triphenylmethane]]
*[[Triphenylmethanol]]
==References==
<references>
<ref name=deno>N. C. Deno, J. J. Jaruzelski, and Alan Schriesheim (1955) "Carbonium ions. I. An acidity function (''C''<sub>0</sub>) derived from arylcarbonium ion equilibria." ''Journal of the American Chemical Society'', voume 77, issue 11, pages 3044–3051. </ref>
<ref name=Urch></ref>
</references>
July 24, 2019 at 04:26PM
