Comparison of calculated hydrocarbon strain energies using ab initio and composite methods

Walker, James; Adamson, P.A; Davis, Steven R.

doi:10.1016/s0166-1280(99)00149-9

Cited by 34 publications

(33 citation statements)

References 19 publications

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“…In recent years studies of ring strain have included larger hydrocarbons [23][24][25][26] and other homocyclic systems [27][28][29][30][31][32]. Relatively few studies, however, have dealt with the computation of strain energy in heterocyclic systems [10,[33][34][35][36].…”

mentioning

confidence: 99%

Conventional strain energy in the oxadiazetidines

Benton

Magers

2004

Int J of Quantum Chemistry

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ABSTRACT:The conventional strain energies for all four isomers of oxadiazetidine are determined within the isodesmic, homodesmotic, and hyperhomodesmotic models. Optimum equilibrium geometries, harmonic vibrational frequencies, and corresponding electronic energies are computed for all pertinent molecular systems using self-consistent field theory, second-order perturbation theory, and density functional theory (DFT) and employing two basis sets of triple-zeta valence quality: 6-311G(d,p) and 6-311ϩG(2df,2pd). The DFT functional employed is Becke's three-parameter hybrid functional using the Lee, Yang, and Paar correlation functional. Single-point fourth-order perturbation theory and coupled-cluster theory restricted to single and double excitations [CCSD(T)] calculations employing the larger basis set also are computed, at both the second-order Møller-Plesset (MP2)/6-311G(d,p) and the MP2/6-311ϩG(2df,2pd) optimized geometries, to determine the effect of higher-order correlation effects on strain energy computation and to gauge the effect of geometry on these effects. Using the same models and methods, the conventional strain energies for both isomers of oxazetidine also are computed, to determine the effect on the strain energy of replacing a nitrogen with a carbon in the ring.

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mentioning

confidence: 99%

Conventional strain energy in the oxadiazetidines

Benton

Magers

2004

Int J of Quantum Chemistry

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“…Various reactions have been suggested in the literature ranging from isogyric to isodesmic to homodesmotic forms [37,38]. Among them, the relatively accurate is homodesmotic schemes [39][40][41][42][43] in which not only the number of various bonds is conserved but also the valence environment around each atom is preserved to raise the advantage of canceling of systematic errors [44].…”

Section: Computational Detailsmentioning

confidence: 99%

“…DFT methods have been proved accurate for computing HOF through appropriate reactions [21][22][23][24][25][62][63][64][65]. In the present work, we calculated the HOFs of S1 and S2 by reaction (1) and (2) Table 4 collects the total energies (E 0 ) and SEs of the species involved in the reactions.…”

Section: Strain Energy and Heat Of Formationmentioning

confidence: 99%

Theoretical Insight into the Structure, Energetic Property and Thermal Stability of C6N6H12 Cages

Zhang¹,

Chen²,

Gong³

2017

J Phys Chem Biophys

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“…The geometric parameters for 1 have been reported at the Hartree-Fock (HF) and MP2 levels by Balaji and Michl [3], who found that the molecule belongs to the C 2V point group. The structure is highly strained and calculated strain energies of 109.8 kcal/mol at the HF/6-31G(d,p) level [3] and 106.5 kcal/mol at the QCISD(T)/6-311ϩG(2df,p)/ MP2/6-311G(d,p) level [4] have been reported.…”

Section: Introductionmentioning

confidence: 96%

“…The sixcarbon analog, tricyclo[3.1.0.0 2,6 ]hexane (3), has been shown to follow a conrotatory process leading to the (E,Z)-1,3-cyclohexadiene intermediate (4), which subsequently isomerizes to give cyclohexadiene (5) (Scheme 1). However, the intermediate 4 is a shallow minimum on the potential energy surface with an activation barrier of only 2.8 kcal/mol for trans double-bond rotation [5].…”

Section: Introductionmentioning

confidence: 99%

MCSCF study of the thermal isomerization of tricyclo[2.1.0.0^2,5]pentane to 1,3‐cyclopentadiene

Davis

Qin

Zhao

2003

Int J of Quantum Chemistry

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ABSTRACT:The isomerization of tricyclo[2.1.0.0 2,5 ]pentane to 1,3-cyclopentadiene was studied using ab initio calculations at the multiconfiguration self-consistent field level of theory. Single-point energy calculations were also performed using the MCQDPT2 and CCSD(T) methods. The isomerization process was found to proceed through a concerted, asynchronous pathway characterized as a disrotatory ring opening of the bicyclobutane moiety. The activation barrier was found to be 42 kcal/mol.

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Comparison of calculated hydrocarbon strain energies using ab initio and composite methods

Cited by 34 publications

References 19 publications

Conventional strain energy in the oxadiazetidines

Conventional strain energy in the oxadiazetidines

Theoretical Insight into the Structure, Energetic Property and Thermal Stability of C6N6H12 Cages

MCSCF study of the thermal isomerization of tricyclo[2.1.0.0^2,5]pentane to 1,3‐cyclopentadiene

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Comparison of calculated hydrocarbon strain energies using ab initio and composite methods

Cited by 34 publications

References 19 publications

Conventional strain energy in the oxadiazetidines

Conventional strain energy in the oxadiazetidines

Theoretical Insight into the Structure, Energetic Property and Thermal Stability of C6N6H12 Cages

MCSCF study of the thermal isomerization of tricyclo[2.1.0.02,5]pentane to 1,3‐cyclopentadiene

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MCSCF study of the thermal isomerization of tricyclo[2.1.0.0^2,5]pentane to 1,3‐cyclopentadiene