The effect of fullerene and some electron donating/withdrawing substituents on the molecular orbitals, strength and the nature of CN bond in a number of RCHNR′ imines: A theoretical study

•E and Z isomers of RCHNR′ compounds are studied.•NBO analysis, interaction energies and relative stabilities are investigated.•The type of molecular orbitals and the energy gap between them is studied.•Electron withdrawing group on nitrogen atom increases the stability of imine.•Fullerene substituent changes the type of frontier orbitals of imine molecules.

A theoretical study on the E and Z isomers of RCHNR′ compounds (R = R′, R ≠ R′; R or R′ = CH3, CF3, ph or t-Bu) as well as E isomer of RCHNCH3 and CH3CHNR (R = C60H or C60CH) molecules is reported. NBO analysis and DFT calculations were used to investigate the effect of R and R′ groups on the strength and the nature of CN bond in above imines. The relative stabilities of RCHNR′ and R′CHNR isomers is also compared. Furthermore, in all compounds the type of π and π* and also HOMO and LUMO molecular orbitals and the energy gap between them is studied. Also three types of anomeric effect in imine compounds having CH3, CF3, ph or t-Bu substituted groups have been assigned.

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