The DFT study on the reaction between benzaldehyde and 4-amine-4H-1,2,4-triazole and their derivatives as a source of stable hemiaminals and schiff bases. Effect of substitution and solvation on the reaction mechanism
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2606-4 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2606-4 | ||
| 245 | 0 | 4 | |a The DFT study on the reaction between benzaldehyde and 4-amine-4H-1,2,4-triazole and their derivatives as a source of stable hemiaminals and schiff bases. Effect of substitution and solvation on the reaction mechanism |h [Elektronische Daten] |c [Slawomir Berski, Agnieszka Gordon, Leszek Ciunik] |
| 520 | 3 | |a Reaction mechanism for the benzaldehyde (ald) and 4-amine-4H-1,2,4-triazole (4at) has been investigated at the DFT (B3LYP)/6-31+G(d) computational level. Three transition states (TS) have been identified. The TS1 corresponds to hydrogen transfer from the NH2 group to the C = O bond and nucleophillic attack of the carbon atom from the aldehyde group on the nitrogen atom from the NH2 group in 4at. The result of this reaction is the hemiaminal molecule. The TS2 characterises an internal rearrangement of the benzene and triazole rings in the hemiaminal molecule. The TS3 leads to breaking of the O-H bond, the elimination reaction of the H2O molecule, and formation of the C=N bond. The final product of this reaction is a Schiff base. In order to determine the most favorable conditions for hemiaminal formation, the influence of electronic structure modification on the energetic properties during the reaction of benzaldehyde and 4-amine-4H-1,2,4-triazole has been studied. Thirteen substituents: NH2, OH, OCH3, CH3, F, I, Cl, Br, COH, COOH, CF3, CN, NO2, with different Hammett's constant values (σ = −0.66-+0.78) have been considered. Finally, the reaction mechanism has been investigated in the presence of 1 to 5 water molecules. Graphical Abstract The R substituent effect on the energetics of the reaction between (modified) benzaldehyde (R-ald) and 4-amine-4H-1,2,4-triazole | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Bonding |2 nationallicence | |
| 690 | 7 | |a DFT |2 nationallicence | |
| 690 | 7 | |a ELF |2 nationallicence | |
| 690 | 7 | |a Hammett constant |2 nationallicence | |
| 690 | 7 | |a Hemiaminal |2 nationallicence | |
| 690 | 7 | |a Mechanism |2 nationallicence | |
| 690 | 7 | |a Schiff |2 nationallicence | |
| 690 | 7 | |a Substituent |2 nationallicence | |
| 700 | 1 | |a Berski |D Slawomir |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | |
| 700 | 1 | |a Gordon |D Agnieszka |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | |
| 700 | 1 | |a Ciunik |D Leszek |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-17 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2606-4 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2606-4 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Berski |D Slawomir |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Gordon |D Agnieszka |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ciunik |D Leszek |u Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383, Wroclaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-17 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | ||