Abstract
Taking formamidine (gas phase proton affinity ≈950 kJ mol−1) and guanidine (gas phase proton affintiy ≈990 kJ mol−1) as the prototype iminoamines with resonance-stabilized cations, similar non-cyclic analogs based on a conjugated carbon atom backbone are studied computationally. A simple model of the charge delocalization is developed which predicts theoretical maximum gas-phase proton affinties (PAs) of ≈1114 kJ mol−1 (unbranched), 1154 kJ mol−1 (singly-branched) and 1209 kJ mol−1 (doubly-branched) for such systems. It is also shown that the 1H and 15N chemical shifts of the protons and nitrogens in the imine functions correlate both with basicity and with atoms-in-molecules multipole moments. The properties of these and related compounds are discussed in the context of proton sponges or superbases.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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