The use of two metal systems cis-Pt(NHC)2Me2 and cis-Ir(NHC)(CO)2Cl help to highlight the flexibility of a series of cycloalkyl-substituted N-heterocyclic carbene ligands (ICy, ICy7, ICy8, ICy12). Bond dissociation enthalpies of several N-heterocyclic carbenes (NHCs) in cis-Pt(NHC)2Me2 are estimated. Electronic and steric parameters of the ICyn ligands are quantified and discussed.