Theoretical study of the Diels–Alder reaction between the S-methylthiophenium ion and ethene

Jursic, Branko S.; Здравковски, Зоран; Whittenburg, Scott L.

doi:10.1039/p29960000455

Cited by 41 publications

(48 citation statements)

References 36 publications

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“…As far as the OMe addition is concerned, in agreement with previous calculations, 17,18,20 the E = values calculated at the B3LYP/6-31G(d) level are the lowest ones and this is also true for the E 1 term defined Figure 6. The use of larger basis sets dramatically increases B3LYP barrier heights, which become larger than their PMP2 counterparts.…”

Section: Barrier Heights and Kinetic Parameterssupporting

confidence: 90%

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Quantum mechanical study of regioselectivity of radical additions to substituted olefins

2000

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Section: Barrier Heights and Kinetic Parameterssupporting

confidence: 90%

“…As mentioned by us 18,20 and others, 8,17 B3LYP reaction energies are too low with respect to post-HF calculations; this is also true for the difference in reaction energies of E r (a) − E r (r).…”

Section: Reaction Energies and Reaction Enthalpiesmentioning

confidence: 90%

Quantum mechanical study of regioselectivity of radical additions to substituted olefins

2000

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“…We have demonstrated that the single point hybrid DFT calculations on AM1 optimized geometries produce activation energies of the DielsAlder reactions that are 1-3 kcal away from the experimental results. 12 The motivation for this paper is twofold. First, although DFT calculations are becoming a very popular tool for the computational chemist excluding ourselves, there are not very many studies which use the hybrid DFT methods for solving systems which are difficult by using quantum chemistry methods.…”

Section: Introductionmentioning

confidence: 99%

Computation of electron affinities of O and F atoms, and energy profile of F–H2 reaction by density functional theory and ab initio methods

Jursic

1996

The Journal of Chemical Physics

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The validity of hybrid and nonlocal DFT methods are tested on examples of systems which are difficult to model by way of quantum chemistry techniques. The electron affinities for the oxygen and fluorine atoms were calculated. The exothermicity, the barrier for the fluorine atom reaction with the hydrogen molecule, and the energy of the H-F bond and its distance were computed with DFT methods, as well as, with ROHF, MPn, and QCISD͑T͒ ab initio methods. The computations were performed by using various basis sets, with 6-311ϩϩG (3d f ,3pd) as the largest. The obtained results are compared with the experimental values. The results of the Becke3LYP hybrid method is in qualitative agreement with experimental results and in the majority of the cases reassembles the high cost QCISD͑T͒ calculation results. Considering the modest computational cost for DFT methods, Becke3LYP/6-311ϩG(2d,2p) is suggested as the standard theory model for computation, and Becke3LYP/6-311ϩϩG(3d f ,3pd) as the model for generating highly accurate results. They should be applicable to relatively sizable chemical systems.

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“…According to the bond order uniformity approach the ring systems that have the most uniform bond order distributions are the most stable and aromatic ones. 45 This can be estimated by the bond order deviations from an average bond order; i.e., for delocalized system of benzene that contains 6 π electrons over 6 carbons average bond order is 1.5. According to our computational study, the structure of heterocycle 2 produces more uniform (more aromatic) ring system.…”

Section: Geometry Parameters and Reactivity Descriptorsmentioning

confidence: 99%

A theoretical approach to the nucleophilic behavior of benzofused thieno[3,2-b]furans using DFT and HF based reactivity descriptors

Vektarienė¹,

Vektaris²,

Svoboda³

2009

Arkivoc

131

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Calculations of traditional HF and DFT based reactivity descriptors are reported for the isomeric benzofused thieno [3,2-b]furans in order to get insight into the factors determining the nature of their interactions with electrophiles. Global reactivity descriptors such as ionization energy, molecular hardness, electrophilicity, frontier molecular orbital energies and shapes, the condensed Fukui functions, total energies were determined and used to identify the differences in the stability and reactivity of benzofused thieno[3,2-b]furans. Additionally the bond order uniformity analysis, local ionization energy and electrostatic potential energy surfaces revealed structural differences of isomeric thieno[3,2-b]furans. Calculated values lead to the conclusion that heterocyclic system in thieno [3,2-b]benzofuran is more aromatic and stable than in isomeric benzothieno [3,2-b]furan. Theoretical results are in complete agreement with the experimental results and show exceptional reactivity of C(2) atom for both isomers.

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Theoretical study of the Diels–Alder reaction between the S-methylthiophenium ion and ethene

Cited by 41 publications

References 36 publications

Quantum mechanical study of regioselectivity of radical additions to substituted olefins

Quantum mechanical study of regioselectivity of radical additions to substituted olefins

Computation of electron affinities of O and F atoms, and energy profile of F–H2 reaction by density functional theory and ab initio methods

A theoretical approach to the nucleophilic behavior of benzofused thieno[3,2-b]furans using DFT and HF based reactivity descriptors

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