Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Alomari, Mohammed I.; Ababneh, Taher S.; Al‐Shboul, Tareq M. A.

doi:10.1142/s0219633617500419

Cited by 2 publications

(1 citation statement)

References 29 publications

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“…The relative energy between the most stable conformer and the less stable ones or the transition states was obtained using the same approach explained in our previous works (also see the supporting information). [30,31] The natural bond orbital (NBO) analysis [32] was carried out using CCSD/6-311G + (d) level of theory to get the point charges of all atoms of each conformer. The obtained data were used to calculate the dipole moment (μ) of the nitrile groups of succinonitrile.…”

Section: Computational Detailsmentioning

confidence: 99%

Conformational Relative Stability and Thermal Properties of Succinonitrile in Gas and Condensed Phases: Using CCSD and DFT Calculations

Alomari

2020

ChemistrySelect

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The geometry and relative stability of succinonitrile in the gas phase have been studied using DFT and ab initio calculations. The trans 1(A) and gauche 1(B) conformers found in succinonitrile are stemmed from the different positions of the two nitrile groups relative to each other. Our results suggest that the trans conformer is more stable than the gauche geometry by 0.65 and 1.01 kcal/mol using the CCSD/6‐311G+(d) and M06/ aug‐cc‐pVDZ calculations, respectively. The results from population analysis indicate that the gas phase is 64.4 % abundant of trans conformer. To imitate the crystal phase, unit cells containing four succinonitrile molecules have been optimized. The data suggest that the trans molar volume of the condensed phase 5(A, B) is smaller than the gauche form 4(A, B, C) by ∼50 Å3 per unit cell. Therefore, at extremely high pressures of up to about 2.9 GPa, the trans conformer predominates. On the contrary, the gauche conformer becomes the predominant isomer as the temperature of the system decreases. This is attributed to the higher stability exhibited by the gauche conformer unit cells compared to that of the trans conformer.

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Section: Computational Detailsmentioning

confidence: 99%

Conformational Relative Stability and Thermal Properties of Succinonitrile in Gas and Condensed Phases: Using CCSD and DFT Calculations

Alomari

2020

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Computational study of n-butyronitrile in gas and condensed phases: conformational relative stability and thermal properties

Alomari

2018

J Chem Sci

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Geometrical structures and relative stability of gauche and trans butyronitrile conformers have been investigated by utilizing ab initio and DFT calculations. The results showed that the gauche conformer is more stable by 0.27 kcal/mol, outlined as enthalpy change H between the two conformers, at CCSD/6-311G+(d,p), the highest level of theory used. Also, the population analysis displays that the gauche conformer is present at 70% in the gas phase, more predominant than the trans conformer. These results agree well with the previous experimental and theoretical findings. Additionally, thermodynamic properties of the two conformers have been investigated. The data exhibit that the abundance of the gauche conformer increases as the temperature decreases under high-pressure condition. The results help to understand the reasons behind the conformational transitions between the fluid and the solid phases.

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Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Cited by 2 publications

References 29 publications

Conformational Relative Stability and Thermal Properties of Succinonitrile in Gas and Condensed Phases: Using CCSD and DFT Calculations

Conformational Relative Stability and Thermal Properties of Succinonitrile in Gas and Condensed Phases: Using CCSD and DFT Calculations

Computational study of n-butyronitrile in gas and condensed phases: conformational relative stability and thermal properties

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