Supramolecular arrangement in mono and bi-camphor acyl hydrazones: A structural study

• Supramolecular arrangements of camphor acyl hydrazones by hydrogen bonding to water.
• Z stabilization, in Z/E isomerisation, by intramolecular hydrogen bonding.
• New roles for the biologically active camphor scaffold.

New acyl hydrazones were synthesized by condensation with camphorquinone aiming at extending the range of applications of the biologically active camphor compounds and structural studies by XRD, 1H-NMR and IR were used in conjunction with advanced computational methodologies to understand the new structural chemistry enabled by the conjugation of the camphor ketone group to the hydrazone NC double bond. In particular, were analysed supramolecular arrangements either by hydrogen bonding to water molecules or electrostatic interactions with non protic solvents. The relative stability of all conformers (E/Z) prompted by the hydrazone bond was addressed by state of the art methods such as CR-CCSD(T) and their inter-conversion in both S0 and S1 by CR-EOM-CCSD(T).

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