RELATIVE STABILITIES OF NITRENIUM IONS DERIVED FROM HETEROCYCLIC AMINE FOOD CARCINOGENS - RELATIONSHIP TO MUTAGENICITY

The bacterial mutagenicities of a wide variety of complex heteroaromatic amine mutagens and carcinogens present in cooked foods are approximately related to the stabilities of the corresponding nitrenium ions through equations of the kind: log(m) = a-DELTA-DELTA-H + b. The stabilities of the nitrenium ions (DELTA-DELTA-H) were computed using the semiempirical AM1 molecular orbital procedure. Parallel calculations of the energies, charge distributions and geometries of simple model compounds provides a qualitative framework within which the stabilities of the nitrenium ions derived from the food carcinogens can be easily understood.