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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
12.6K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

9.2K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
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MO Theory and Covalent Bonding02:40

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10.6K
The molecular orbital theory describes the distribution of electrons in molecules in a manner similar to the distribution of electrons in atomic orbitals. The region of space in which a valence electron in a molecule is likely to be found is called a molecular orbital. Mathematically, the linear combination of atomic orbitals (LCAO) generates molecular orbitals. Combinations of in-phase atomic orbital wave functions result in regions with a high probability of electron density, while...
10.6K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

1.8K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Open shell versus closed shell bonding interaction in cyclopropane derivatives: EDA-NOCV analyses.

Sonam Suthar1, Kartik Chandra Mondal1

  • 1Department of Chemistry, Indian Institute of Technology Madras, Chennai, India.

Journal of Computational Chemistry
|August 2, 2023
PubMed
Summary

The chemical bonding in most cyclopropane rings involves dative covalent bonds, differing from typical electron-sharing bonds. This finding offers a more general bonding model for these common organic structures.

Keywords:
DFT calculationEDA-NOCVchemical bonding of cyclopropane ringelectron-sharing covalent bond versus dative covalent bondopen shell versus closed shell interactions

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Quantum Chemistry

Background:

  • Cyclopropane rings are prevalent in organic and bio-organic compounds, featuring unique strained C3 rings.
  • The chemical bonding and reactivity of cyclopropanes have been debated for over a century, with models like Bent-Bond and Walsh.
  • Understanding cyclopropane bonding is crucial for rationalizing their stability, reactivity, and physical properties.

Purpose of the Study:

  • To investigate the bonding nature of cyclopropane C-C bonds using advanced computational methods.
  • To develop a more general bonding model for cyclopropane rings by analyzing diverse functionalized compounds.
  • To elucidate the influence of functional groups on the chemical bonding within cyclopropane systems.

Main Methods:

  • Employed Energy Decomposition Analysis coupled with Natural Orbital for Chemical Valence (EDA-NOCV) on 49 different organic compounds containing cyclopropane rings.
  • Analyzed fragment orbitals and bond formation to characterize the nature of the C-C bonds within the cyclopropane ring.
  • Utilized Quantum Theory of Atoms in Molecules (QTAIM) analysis to complement EDA-NOCV findings.

Main Results:

  • The EDA-NOCV analysis revealed that the majority of cyclopropane C-C bonds (37/49 compounds) prefer forming two dative covalent bonds over two electron-sharing bonds.
  • A smaller fraction of compounds (7/49) exhibited electron-sharing bonds, while some (5/49) showed flexibility between both bonding types.
  • QTAIM analyses supported these findings, showing distinct parameters for cyclopropane C-C bonds compared to typical hydrocarbon single bonds.

Conclusions:

  • The predominant bonding in cyclopropane rings involves dative covalent interactions, challenging traditional bonding descriptions.
  • The study provides a more generalized bonding model for cyclopropanes, applicable across various functionalized systems.
  • The bonding characteristics of cyclopropane rings share similarities with metal-olefin systems.