Interaction of methanol with some aniline and pyrrole derivatives: DFT calculations

• Interaction of methanol on aniline derivatives (nANI) and pyrrole derivatives (mPY).
• Higher physisorption energy of methanol on terpyrrole than dianiline.
• Notable orbital hybridization between methanol with nANI as well as mPY.
• mPY has a more sensitive sensor toward methanol detection than nANI.

The interaction of methanol with two aniline derivatives (denoted as nANI, n = 2 and 4 for dianiline and tetraaniline,2 and 4 respectively) and also with two pyrrole derivatives (denoted as mPY, m = 3 and 5 for terpyrrole and pentapyrrole, respectively) were investigated and compared to each other using density functional theory (DFT) at a level of BLYP-D3/6-31+G(d,p). The computed density of states (DOS) showed that some orbital hybridization takes place during interaction of methanol with dianiline and terpyrrole. Natural population analysis (NPA) was used to find out the charge distribution as well as the net transferred charge of dianiline-M and terpyrrole-M complexes to assess the sensing ability of nANI and mPY systems. When methanol approaches to the nANI and mPY, the amount of the dielectric (μD) changes depend on the interaction configurations. As a result, the electronic properties of nANI and mPY are sensitive to methanol based on the calculated changes in the HOMO_LUMO energy gap. The interaction energy values of methanol were calculated about −14.9, −13.7, −24.3, and −22.8 kJ mol−1 upon interaction with dianiline, tetraaniline, terpyrrole, and pentapyrrole, respectively.

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