TOWARD ENGINEERING OF VERY STRONG ORGANIC-BASES - PRONOUNCED PROTON AFFINITY OF MOLECULES POSSESSING IMINO STRUCTURAL AND ELECTRONIC MOTIF

The absolute proton affinity of a group of compounds involving AN imin o group is examined by employing the MP2(fc)/6-311+G*//HF/6-31G*+ZPVE (HF/6-31G) theoretical model. It appears that these systems exhibit h igh proton affinity thus representing good candidates for efficient pr oton sponges. Their heavily substituted derivatives, involving bulky a lkyl groups, which protect the reactive double bonds, should possess e ven higher proton affinity being at the same time apt to chemical synt hesis. (C) 1998 Elsevier Science B.V. All rights reserved.