cycloadducts. They also undergo insertion into the C–Cl bonds of acyl chlorides in the Nef isocyanide reaction, a process that is believed to be concerted and illustrates their carbene character. Isocyanides have also been shown to be a useful reagent in palladium catalysed reactions with a wide variety of compounds being formed using this method. The α position of isocyanides have substantial acidity. For example, benzyl isocyanide has a pKa of 27.4. In comparison, benzyl cyanide has a pKa of 21.9. In the gas phase, is 1.8 kcal/mol less acidic than . Chlorination of isocyanides gives isocyanide dichlorides. Ligands in coordination chemistry Isocyanides form coordination complexes with most transition metals. They behave as electron-rich analogues of carbon monoxide. For example tert-butyl isocyanide forms , which is analogous to . Although structurally similar, the analogous carbonyls differ in several ways, mainly because t-BuNC is a better donor ligand than CO. Thus, is easily protonated, whereas its counterpart is not. Naturally occurring isocyanides Only few naturally occurring compounds exhibit the isocyanide functionality. The first was discovered in 1957 in an extract of the mold Penicillium notatum. The compound xanthocillin later was used as an antibiotic. Since then numerous other isocyanides have been isolated. Most of the marine isocyanides are terpenoid, while some of the terrestrial isocyanides originate from α-aminoacids. Nomenclature IUPAC uses the prefix "isocyano" for the systematic nomenclature of isocyanides: isocyanomethane, isocyanoethane, isocyanopropane, etc. The sometimes used old term "carbylamine" conflicts with systematic nomenclature. An amine always has three single bonds, whereas an isocyanide has only one single and one multiple bond. The isocyanamide functional group consists of a amino group attached to an isocyano moiety. for nomenclature as suffix of isonitrile or prefix of isocyano is used depending upon priority table. References Functional groups