6-Aminofulvene-1-aldimine: A Model Molecule for the Study of Intramolecular Hydrogen Bonds

Abstract

The search for new systems that sustain phenomena such as intramolecular hydrogen bonds (IMHB), [1,2] proton transfer along hydrogen bonds, [3,4] and coupling constants through hydrogen bonds, [5,6] led us to select 6-aminofulvene-1-aldimines. These compounds were reported in the 1970s by Müller-Westerhoff and Ammon, who determined the X-ray structure of 1 and its NMR spectroscopic properties in solution. [8,9] [4] a)

Verification of a Designed Intramolecular Hydrogen Bond in a Drug Scaffold by Nuclear Magnetic Resonance Spectroscopy

“…23,24 Similarly, scalar couplings across intramolecular H bonds have been detected in smallmolecule model systems. [25][26][27][28][29][30] These studies generally require isotope labeling of the macromolecule or model compound, and for small molecules, the NMR measurements often need to be performed at low temperatures, 13 in the solid state, 31 or at multiple magnetic fields. 30 Scalar couplings across H bonds have been interpreted as evidence of their partial covalent nature.…”