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Atomic carbon

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Atomic carbon

Atomic carbon
Names
Preferred IUPAC name
Atomic carbon
Systematic IUPAC name
Methanediylidene (substitutive)
Carbon (additive)
Identifiers
ChEBI  YesY
ChemSpider  YesY
Jmol-3D images Image
PubChem
Properties
C
Molar mass 12.01 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY  (: YesY/N?)

Atomic carbon (systematically named methanediylidene and carbon), also called monocarbon, is an chemical with the chemical formula C (also written [C]). It is a gas that only exists above 3,642 °C (6,588 °F), below which it aggregates into graphite or other fullerenes.

Nomenclature

The trivial name monocarbon is the preferred IUPAC name. The systematic names, methanediylidene and carbon, valid IUPAC names, are constructed according to the substitutive and additive nomenclatures, respectively.

Methanediylidene is viewed as methane with all four hydrogen atoms removed. By default, this name pays no regard to the radicality of the atomic carbon. Although, in even more specific context, it can also name the non-radical excited states, whereas the radical ground state with two unpaired electrons is named methanediylylidene.

Chemical Properties

Radicality

Many of atomic carbon's electronic states lie relatively close to each other, giving rise to varying degrees of radical chemistry. The ground state is a triplet radical with two unpaired electrons (X3P0), and the first two excited states are a singlet non-radical (a1D2) and a singlet radical with two unpaired electrons (b1S0). A sample of atomic carbon exists as a mixture of electronic states even at room temperature, giving rise to complex reactions. For example, reactions of the triplet radical with non-radical species generally involves abstraction, whereas reactions of the singlet non-radical involves not only abstraction, but also insertion or addition.

[C]2•(X3P0) + H
2
O
→ [CH] + [HO]
[C](a1D2) + H
2
O
→ [CO] + H
2
or H
2
CO

Amphotericity

Atomic carbon accept an electron-pair donating ligand into the molecule by adduction:[1]

[C] + :L → [CL]

Because of this acceptance of the electron-pair donating ligand, atomic carbon has Lewis-acidic character.[2] Atomic carbon can accept two such ligands. An example is C(CO)
2
.

The methylylidyne group can also donate an electron-pair to an accepting centre by adduction:

M + [C] → [MC]

Because of this donation of the electron-pair, atomic carbon has Lewis-basic character. An example is [Au
6
C(PPh
3
)
6
]2+
. Since a Lewis base is also Brønsted base,[2] atomic carbon can in theory be protonated to form a conjugate acid, which is methyliumylidene or hydridocarbon(+) (CH+
). Atomic carbon is not stable in aqueous solution, as it is rapidly oxidized to form carbon monoxide or formaldehyde.[1]

Chemical reactions

Atomic carbon is highly reactive, most reactions are very exothermic. They are generally carried out in the gas phase at liquid nitrogen temperatures (77 K). Typical reactions with organic compounds include:[3]

Insertion into a C-H bond in alkanes to form a carbene
Deoxygenation of carboxyl groups in ketones and aldehydhdes to form a carbene, 2-butanone forming 2-butanylidene.
Insertion into carbon -carbon double bonds to form a cyclopropylidene which undergoes ring-opening, a simple example being insertion into an alkene to form a cumulene.

With water insertion into the O-H bond forms the carbene, H-C-OH that rearranges to formaldehyde, HCHO.

Normally, a sample of atomic carbon exists as a mixture of excited states in addition to the ground-state in thermodynamic equilibrium. Each state contributes differently to the reaction mechanisms that can take place. A simple test used to determine which state is involved is to make use of the diagnostic reaction of the triplet state with O2, if the reaction yield is unchanged it indicates that the singlet state is involved. The diradical ground-state normally undergoes abstraction reactions. Atomic carbon has been used to generate "true" carbenes by the abstraction of oxygen atoms from carbonyl groups:

R2C=O + :C: → R2C: + CO

Carbenes formed in this way will exhibit true carbenic behaviour. Carbenes prepared by other methods such as diazo compounds, might exhibit properties better attributed to the diazo compound used to make the carbene (which mimic carbene behaviour), rather than to the carbene itself. This is important from a mechanistic understanding of true carbene behaviour perspective.

Production

Making atomic carbon :C: - The source of light is the electrical arcing between two carbon rods. Liquid nitrogen cools the reaction vessel. The black substance is soot. This photo was taken in the Laboratory of Professor Phil Shevlin at Auburn University.

This very short lived species is created by passing a large current through two adjacent carbon rods, generating an electric arc. Atomic carbon is generated in the process. Professor Phil Shevlin has done the principal work in the field based at Auburn University in the USA.

The way this species is made is closely related to the formation of fullerenes C60, the chief difference being that a much lower vacuum is used in atomic carbon formation.

References


-- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --


local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno

local p = {}


-- Helper functions


local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end

function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end

function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '
%s
', table.concat(classes, ' '), s )

end

return p-------------------------------------------------------------------------------- -- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --


local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno

local p = {}


-- Helper functions


local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end

function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end

function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '
%s
', table.concat(classes, ' '), s )

end

return p
  1. ^ a b
  2. ^ a b
  3. ^ Reactive Intermediate Chemistry, Robert A. Moss, Matthew S. Platz and Maitland Jones Jr., Wiley-Blackwell, (2004), isbn: 978-0471233244
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