Pyrrole and Pyridine in the Water Environment—Effect of Discrete and Continuum Solvation Models

Abstract

Properties of pyrrole and pyridine molecules upon different hydrations were investigated through density functional theory. Complexes of studied molecules with a cluster of 50 water molecules were considered, and the polarizable continuum model of solvation (PCM) was also taken into account. For comparative purposes, all mentioned calculations were repeated for single pyrrole and pyridine molecules and their complexes with one water molecule. Aromaticities of solvated pyrrole and pyridine rings were studied using several geometric-and electronic-based aromaticity criteria. Special attention was paid to studying the properties of formed hydrogen bonds between pyrrole or pyridine and either a single water molecule or several water molecules of the cluster. Overall, a comprehensive description of two very important heterocyclic compounds, that is, pyrrole and pyridine, in both discrete and continuum water solutions, is extensively presented.

Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity

“…The NICS(1)zz, one of the four NICS indices, will be utilized in further discussion since it provides a more precise measurement of magnetic shielding [ [107] , [108] , [109] , [110] , [111] ]. Our findings in Table 7 show a good agreement with earlier research on pyrrole [ [112] , [113] , [114] ].…”

A Comparative DFT Study on the Antioxidant Activity of Some Novel 3‐Hydroxypyridine‐4‐One Derivatives

“…A recently published study has shown that the effect of the solvent on strongly aromatic compound as pyrrole or pyridine are small. [47] We have previously reported some 3-hydroxypyridin-4-one scaffolds, derived from kojic acid, which exhibit high iron chelating and DPPH radical scavenging activities (Figure 1). The design of these derivatives was performed based on the fact that the free radical scavenging ability increases with a number of conjugated double bonds.…”

“…They can interact more strongly with the solvent molecules than compounds characterized by the high aromaticity. A recently published study has shown that the effect of the solvent on strongly aromatic compound as pyrrole or pyridine are small [47] …”