Attributing to the chemical sensor application based on charge transfer phenomena between the host and the guest for new derivative of calix 4quinone, 1,3-alternate-calix 4quinone (C4Q), have been investigated via DFT-D3 calculation and compared to the experimental data. The structural design of the title molecule has been characterized, and the organic quinone has been clearly identified. The selected sites for the Cu2+, Ag2+ and Hg2+ cations by the calix 4quinone molecule have been discussed. The molecular electrostatic potential (MEP) map has been performed in order to identify the highly attractive site for the selected cations. The 1H NMR chemical shifts of the stable complexes have been calculated. Moreover, the calculated stretching vibrational modes in the most stable conformations have been assigned and compared with the experimental ones. The UV–Vis spectroscopy revealed that the interaction of the Cu2+, Ag2+ (d9 electron configuration) and Hg2+(d10 electron configuration) cations with the C4Q is reinforced with the red shifting to high absorption bands of the free molecule. The HOMO and LUMO orbital iso-surfaces exhibit that the C4Q-Cu2+ complex has the highest charge transfer terms (CTT) which increased the overall energetic stabilization of the system. The Hirshfeld surface (HS) showed the highly attractive energetic binds that favor the efficient charge transfer phenomena between the two systems. The interactions between the host (C4Q) and guest (metal cation) are discussed deeply using the topological AIM and non-covalent RDG index analyses. The computed values from electron density and the binding energies for all active bonds have been interpreted. Finally, the ELF/LOL at bond critical points and ELF maps are computed to confirm and visualize the donor-acceptor couple formed between the selected host-guest systems. Display omitted •Higher metal cations adsorption with C4Q through the electron released exchange process.•Electronic properties identified the charge transfer phenomena between the host and the guest.•The Hirshfeld surface (HS) is used to determine the high attractive energetic binds.•The host-guest interactions are discussed through AIM-RDG and ELF analyses.•C4Q is suitable to have a good performance sensor.