caa a22 4500 60551089X CHVBK 20210128100648.0 cr unu---uuuuu 210128e20150601xx s 000 0 eng 10.1007/s00894-015-2688-z doi (NATIONALLICENCE)springer-10.1007/s00894-015-2688-z Computational simulation study on the anion recognition properties of functionalized tetraphenyl porphyrins [Elektronische Daten] [Ju Xie, Xuesong Chen, Zhiling Huang, Tongfei Zuo] The anion recognitions of tetra-(2-formamido) phenyl porphyrin (APP), tetra-(2-ureido) phenyl porphyrin (UPP), and their zinc derivatives (ZnAPP and ZnUPP) to three anions (Cl−, H2PO4 −, CH3COO−) were studied using quantum mechanical calculations (QM) and molecular dynamics (MD) simulations. The density functional theory (DFT) calculations at M06-2X/6-31G (d, p) level indicated that the anion recognition ability of ZnAPP was better than that of APP, and the anion selectivity was in the order Cl− < H2PO4 − < CH3COO−. The selectivity trends for ZnUPP and UPP were found to be H2PO4 − < Cl− < CH3COO−. The structures, thermodynamic properties, and recognition mechanisms were discussed in detail. The 2ns MD simulations were then carried out for anion@ZnAPP and anion@ZnUPP complexes in mixed solvent DMSO/water. The MD simulation results showed that anion@ZnUPP complexes exhibited higher stability than anion@ZnAPP, which was in good agreement with QM results. H-bonds formed between the anions and the side-chains of receptors, and zinc coordination bonds with anions contributed significantly to the stability of complexes. The anion selectivity of ZnAPP and ZnUPP in the solvent phase were also discussed and compared with those in the gas phase. Springer-Verlag Berlin Heidelberg, 2015 Porphyrin derivative nationallicence Anion recognition nationallicence Quantum chemical calculation nationallicence Molecular dynamics simulation nationallicence Xie Ju College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut Chen Xuesong College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut Huang Zhiling College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut Zuo Tongfei College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/6(2015-06-01), 1-10 1610-2940 21:6<1 2015 21 894 https://doi.org/10.1007/s00894-015-2688-z text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2688-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Xie Ju College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut NATIONALLICENCE 700 1- Chen Xuesong College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut NATIONALLICENCE 700 1- Huang Zhiling College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut NATIONALLICENCE 700 1- Zuo Tongfei College of Chemistry and Chemical Engineering, Yangzhou University, 225002, Yangzhou, China aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/6(2015-06-01), 1-10 1610-2940 21:6<1 2015 21 894