Relationships between basicity, structure, chemical shift and the charge distribution in resonance-stabilized iminoamines

Howard, Sian T., Platts, James Alexis ORCID: https://orcid.org/0000-0002-1008-6595 and Coogan, Michael Peter 2002. Relationships between basicity, structure, chemical shift and the charge distribution in resonance-stabilized iminoamines. Journal of the Chemical Society - Perkins Transactions 2 (5) , pp. 899-905. 10.1039/B200899H

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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.

Item Type:	Article
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1364-5471
Last Modified:	18 Oct 2022 13:09
URI:	https://orca.cardiff.ac.uk/id/eprint/12516

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