Editing Methyl radical (section)

== Chemical properties ==
Its first ionization potential (yielding the [[methenium]] ion, {{chem|CH|3|+}}) is {{val|9.837|0.005|ul=eV}}.<ref name=Golob> {{cite journal | last1 = Golob | first1 = L. | last2 = Jonathan | first2 = N. | last3 = Morris | first3 = A. | last4 = Okuda | first4 = M. | last5 = Ross | first5 = K.J. | year = 1972 | title = The first ionization potential of the methyl radical as determined by photoelectron spectroscopy | journal = Journal of Electron Spectroscopy and Related Phenomena | volume = 1 | issue = 5| pages = 506–508 | doi = 10.1016/0368-2048(72)80022-7 | bibcode = 1972JESRP...1..506G }}</ref>

=== Redox behaviour ===
The carbon centre in methyl can bond with electron-donating molecules by reacting:
:{{Chem|CH|3|•}} + R<sup>•</sup> → {{Chem|RCH|3}}
Because of the capture of the nucleophile (R<sup>•</sup>), methyl has oxidising character. Methyl is a strong oxidant with organic chemicals. However, it is equally a strong reductant with chemicals such as water. It does not form aqueous solutions, as it reduces water to produce [[methanol]] and elemental hydrogen:
:2&nbsp;{{Chem|CH|3|•}} + 2&nbsp;{{Chem|H|2|O}} → 2&nbsp;{{Chem|CH|3|OH}} + {{Chem|H|2}}

=== Structure ===
The [[molecular geometry]] of the methyl radical is [[trigonal planar molecular geometry|trigonal planar]] (bond angles are 120°), although the energy cost of distortion to a [[trigonal pyramidal molecular geometry|pyramidal geometry]] is small.  All other electron-neutral, non-conjugated alkyl radicals are pyramidalized to some extent, though with very small inversion barriers.  For instance, the [[t-Butyl|''t''-butyl]] radical has a bond angle of 118° with a {{cvt|0.7|kcal/mol|kJ/mol}} barrier to [[pyramidal inversion]]. On the other hand, substitution of hydrogen atoms by more electronegative substituents leads to radicals with a strongly pyramidal geometry (112°), such as the  [[trifluoromethyl]] radical, {{chem|CF|3|•}}, with a much more substantial inversion barrier of around {{cvt|25|kcal/mol|kJ/mol}}.<ref>Anslyn E.V. and Dougherty D.A., ''Modern Physical Organic Chemistry'' (University Science Books, 2006), p.57</ref>

=== Chemical reactions ===
Methyl undergoes the typical chemical reactions of a radical. Below approximately {{Convert|1100|C|K|-2}}, it rapidly dimerises to form [[ethane]]. Upon treatment with an alcohol, it converts to [[methane]] and either an alkoxy or hydroxyalkyl. Reduction of methyl gives methane. When heated above, at most, {{Convert|1400|C|K|-2}}, methyl decomposes to produce [[methylidyne]] and elemental hydrogen, or to produce [[methylene radical|methylene]] and atomic hydrogen:
:{{Chem|CH|3|•}} → CH<sup>•</sup> + {{Chem|H|2}}
:{{Chem|CH|3|•}} → {{Chem|CH|2|•}} + H<sup>•</sup>
Methyl is very corrosive to metals, forming methylated metal compounds:
:M + ''n''&nbsp;{{Chem|CH|3|•}} → M(CH<sub>3</sub>)<sub>''n''</sub>