Tautomeric Study of Neutral, Protonated and Deprotonated Isorhodanine Based on High Level Density Functional Theory

Safi, Zaki

doi:10.13005/ojc/320508

Cited by 6 publications

(4 citation statements)

References 36 publications

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“…8,9 As the experimental measurement of the PAs and GBs is difficult, the computation methods have witnessed a great interest last few decades. [10][11][12][13][14][15][16] DFT methods with a large and rational basis set can reproduce a reliable thermochemical and thermodynamic properties for chemical systems. [10][11][12][16][17][18] Previous studies showed that PA and GBs values calculated using the B3LYP method are as efficient possible as high-level ab initio results.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, wide experimental and theoretical efforts were attained to calculate the PA and GB values, especially in gas phase, for example, ion mobility spectrometry (IMS), 5 mass spectrometry (MS), 6,7 calorimetry, kinetic method and ion cyclotron resonance (ICR) mehods 8,9 . As the experimental measurement of the PAs and GBs is difficult, the computation methods have witnessed a great interest last few decades 10–16 . DFT methods with a large and rational basis set can reproduce a reliable thermochemical and thermodynamic properties for chemical systems 10–12,16–18 .…”

Section: Introductionmentioning

confidence: 99%

“…Schematic representation of some p-substituted benzaldehydes T A B L E 5 Predicted proton affinities and gas-phase basicities of some psubstituted benzaldehyde compounds(9)(10)(11)(12)(13)(14)(15)(16) …”

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confidence: 99%

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Benchmark calculations of proton affinity and gas‐phase basicity using multilevel (G4 and G3B3), B3LYP and MP2 computational methods of para‐substituted benzaldehyde compounds

Safi

Wazzan

2021

J Comput Chem

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This study presents the benchmark calculations of proton affinities (PAs) and gas-phase basicities (GBs) of 8-para substituted benzaldehyde compounds using the multilevel model chemistries (G3B3 and G4), density-functional quantum model (B3LYP) and ab initio model (MP2). The results show that the computed properties are strongly correlated with the available experimental data. The PAs and the GBs of other eight para-substituted benzaldehyde compounds, for which the experimental data does not currently exist, have been calculated using G3B3 and B3LYP methods.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Benchmark calculations of proton affinity and gas‐phase basicity using multilevel (G4 and G3B3), B3LYP and MP2 computational methods of para‐substituted benzaldehyde compounds

Safi

Wazzan

2021

J Comput Chem

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“…The ability of an atom or molecule in the gas phase to accept or to lose a proton can be described by calculating the proton affinity (PA), deprotonation (dehydrogenation) enthalpy, and molecular gas-phase basicity, which offer a profound understanding of the connections between the reactivity of the organic molecules, their molecular structures, and molecular stability 16 . The negative of the enthalpy change related to the gas-phase protonation reaction is referred to as proton affinity, while dehydrogenation energy is defined as the enthalpy change related to the gas-phase dehydrogenation reaction 17 .…”

Section: Introductionmentioning

confidence: 99%

Computational study of the unimolecular and bimolecular decomposition mechanisms of propylamine

Almatarneh

Omari

Omeir

et al. 2020

Sci Rep

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A detailed computational study of the dehydrogenation reaction of trans-propylamine (trans-pA) in the gas phase has been performed using density functional method (DFT) and CBS-QB3 calculations. Different mechanistic pathways were studied for the reaction of n-propylamine. Both thermodynamic functions and activation parameters were calculated for all investigated pathways. Most of the dehydrogenation reaction mechanisms occur in a concerted step transition state as an exothermic process. the mechanisms for pathways A and B comprise two key-steps: H 2 eliminated from pA leading to the formation of allylamine that undergoes an unimolecular dissociation in the second step of the mechanism. Among these pathways, the formation of ethyl cyanide and H 2 is the most significant one (pathway B), both kinetically and thermodynamically, with an energy barrier of 416 kJ mol −1. the individual mechanisms for the pathways from c to n involve the dehydrogenation reaction of PA via hydrogen ion, ammonia ion and methyl cation. The formation of α-propylamine cation and nH 3 (pathway E) is the most favorable reaction with an activation barrier of 1 kJ mol −1. this pathway has the lowest activation energy calculated of all proposed pathways. Propylamine is of significant importance in chemistry, as it constitutes a central structure block for aliphatic amines 1. It is widely utilized as a solvent in organic synthesis, and as a finishing agent for drugs, rubber, fiber, paints, pesticides, textile and resin 2,3 , and in the generation of fungicides 4-6. Furthermore, it may very well be used as a petroleum additive and preservative. The disintegration of protonated of propylamine has attracted a noteworthy arrangement of fascination in the previous decade 7-10. This is mainly due to the way that the proton affinity and the structural difference in propylamine through protonation influences the separation items through the arrangement of protonated amines, methane, propene and hydrogen gas 11,12. Additionally, this reaction prompts the generation of various poisonous synthetic substances such as, alkyl cyanide, propylene, ethylene, nitrogen and hydrogen gases 13,14. Protonation (B + H + → BH +) and deprotonation (dehydrogenation) (HA − H + → A −) reactions assume a significant role in natural science and organic chemistry, where A and B are the acidic and the basic centers, respectively. They are considered as the first step in several fundamental chemical mechanisms elucidated in the cited reference 15. The ability of an atom or molecule in the gas phase to accept or to lose a proton can be described by calculating the proton affinity (PA), deprotonation (dehydrogenation) enthalpy, and molecular gasphase basicity, which offer a profound understanding of the connections between the reactivity of the organic molecules, their molecular structures, and molecular stability 16. The negative of the enthalpy change related to the gas-phase protonation reaction is referred to as proton affinity, while dehydrogenation energy is defined as the en...

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PCM/DFT investigation of the hydrogen-bonds capability of 4-[4-(dimethylamino)phenyl]-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile (MAPC)

Al−Qurashi

Wazzan

2017

Journal of Molecular Liquids

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Tautomeric Study of Neutral, Protonated and Deprotonated Isorhodanine Based on High Level Density Functional Theory

Cited by 6 publications

References 36 publications

Benchmark calculations of proton affinity and gas‐phase basicity using multilevel (G4 and G3B3), B3LYP and MP2 computational methods of para‐substituted benzaldehyde compounds

Benchmark calculations of proton affinity and gas‐phase basicity using multilevel (G4 and G3B3), B3LYP and MP2 computational methods of para‐substituted benzaldehyde compounds

Computational study of the unimolecular and bimolecular decomposition mechanisms of propylamine

PCM/DFT investigation of the hydrogen-bonds capability of 4-[4-(dimethylamino)phenyl]-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile (MAPC)

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