Approximate but realistic estimates of bond properties in alkylamines

A simple bond energy scheme featuring the net charges of the bond-forming atoms is applied to alkylamines. The appropriate charge analyses are assisted by accurate correlations with ¹³C and ¹⁵N nuclear magnetic resonance shifts. Intrinsic carbon-nitrogen bond energies were thus calculated and subsequently used in the computation of the corresponding dissociation energies, in good agreement with experiment. (A few examples are also given for the C-N cleavage of nitroalkanes.) Enthalpy calculations are also presented. Additional applications, prospects and limitations are discussed. (C) 2000 Elsevier Science B.V.