Molecular Modeling of Anti-Bredt Compounds

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The molecular structure and thermochemical stability of 40 bicyclic alkenes and imines containing betweenfive and eight heavy atoms has been investigated computationally by high-level G3/B3LYP method. Thesame method was also used to study their building blocks: monocyclic alkenes and imines. The relativestability of isomers, standard enthalpies of formation and strain energies are discussed and compared. Ourresults suggest that molecular mechanics provides an unsatisfactory description of strain energies in bridgeheadalkenes. Some bridgehead alkene and imine species represent structures which are not local minima on thepotential energy surface and are hence unlikely to be isolated. Furthermore, some bicyclic alkenes andimines have open-shell 1,2-diradical character.
Original languageEnglish
Pages (from-to)334-338
Number of pages5
JournalJournal of Chemical Information and Modeling
Volume45
Issue number2
DOIs
Publication statusPublished - 2005

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Molecular modeling
Alkenes
Olefins
Imines
energy
Strain energy
mechanic
Molecular mechanics
Interfacial energy
Isomers
Molecular structure
Enthalpy
Atoms

Cite this

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title = "Molecular Modeling of Anti-Bredt Compounds",
abstract = "The molecular structure and thermochemical stability of 40 bicyclic alkenes and imines containing betweenfive and eight heavy atoms has been investigated computationally by high-level G3/B3LYP method. Thesame method was also used to study their building blocks: monocyclic alkenes and imines. The relativestability of isomers, standard enthalpies of formation and strain energies are discussed and compared. Ourresults suggest that molecular mechanics provides an unsatisfactory description of strain energies in bridgeheadalkenes. Some bridgehead alkene and imine species represent structures which are not local minima on thepotential energy surface and are hence unlikely to be isolated. Furthermore, some bicyclic alkenes andimines have open-shell 1,2-diradical character.",
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Molecular Modeling of Anti-Bredt Compounds. / Novak, Igor.

In: Journal of Chemical Information and Modeling, Vol. 45, No. 2, 2005, p. 334-338.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Molecular Modeling of Anti-Bredt Compounds

AU - Novak, Igor

N1 - Imported on 12 Apr 2017 - DigiTool details were: Journal title (773t) = Journal of Chemical Information and Modeling. ISSNs: 1549-9596;

PY - 2005

Y1 - 2005

N2 - The molecular structure and thermochemical stability of 40 bicyclic alkenes and imines containing betweenfive and eight heavy atoms has been investigated computationally by high-level G3/B3LYP method. Thesame method was also used to study their building blocks: monocyclic alkenes and imines. The relativestability of isomers, standard enthalpies of formation and strain energies are discussed and compared. Ourresults suggest that molecular mechanics provides an unsatisfactory description of strain energies in bridgeheadalkenes. Some bridgehead alkene and imine species represent structures which are not local minima on thepotential energy surface and are hence unlikely to be isolated. Furthermore, some bicyclic alkenes andimines have open-shell 1,2-diradical character.

AB - The molecular structure and thermochemical stability of 40 bicyclic alkenes and imines containing betweenfive and eight heavy atoms has been investigated computationally by high-level G3/B3LYP method. Thesame method was also used to study their building blocks: monocyclic alkenes and imines. The relativestability of isomers, standard enthalpies of formation and strain energies are discussed and compared. Ourresults suggest that molecular mechanics provides an unsatisfactory description of strain energies in bridgeheadalkenes. Some bridgehead alkene and imine species represent structures which are not local minima on thepotential energy surface and are hence unlikely to be isolated. Furthermore, some bicyclic alkenes andimines have open-shell 1,2-diradical character.

KW - Molecular modelling

U2 - 10.1021/ci0497354

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