Editing Acetonitrile (section)

===As an electron pair donor===
Acetonitrile has a free electron pair at the nitrogen atom, which can form many [[transition metal nitrile complexes]]. Being weakly basic, it is an easily displaceable [[ligand]]. For example, [[bis(acetonitrile)palladium dichloride]] is prepared by heating a suspension of [[palladium chloride]] in acetonitrile:<ref>{{Cite book|title=Organic synthesis : concepts and methods|last=Jürgen-Hinrich.|first=Fuhrhop|date=2003|publisher=Wiley-VCH|others=Li, Guangtao, Dr.|isbn=9783527302727|edition=3rd, completely rev. and enl.|location=Weinheim|oclc=51068223|page=26}}</ref>
:{{chem2|PdCl2 + 2 CH3CN -> PdCl2(CH3CN)2}}
A related complex is [[tetrakis(acetonitrile)copper(I) hexafluorophosphate]] {{chem2|[Cu(CH3CN)4]+}}. The {{chem2|CH3CN}} groups in these complexes are rapidly displaced by many other ligands.

It also forms Lewis adducts with group 13 [[Lewis acid]]s like [[boron trifluoride]].<ref>B. Swanson, D. F. Shriver, J. A. Ibers, "Nature of the donor-acceptor bond in acetonitrile-boron trihalides. The structures of the boron trifluoride and boron trichloride complexes of acetonitrile", Inorg. Chem., 2969., volume 8, pp. 2182-2189, {{doi:10.1021/ic50080a032}}</ref> In [[superacid]]s, it is possible to protonate acetonitrile.<ref name="Christe">{{cite journal|last1 = Haiges|first1=Ralf|last2=Baxter|first2=Amanda F.|last3=Goetz|first3=Nadine R.|last4=Axhausen|first4=Joachim A.|last5=Soltner|first5=Theresa|last6=Kornath|first6=Andreas|last7=Christe|first7=Kalr O.|title=Protonation of nitriles: isolation and characterization of alkyl- and arylnitrilium ions|journal=Dalton Transactions|year=2016|volume=45|issue=20|pages=8494–8499|doi=10.1039/C6DT01301E|pmid=27116374}}</ref>