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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Radicals: Electronic Structure and Geometry01:07

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

12.6K
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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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
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Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

14.7K
Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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A Rhodium-Pentane Sigma-Alkane Complex: Characterization in the Solid State by Experimental and Computational

F Mark Chadwick1, Nicholas H Rees1, Andrew S Weller2

  • 1Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

Angewandte Chemie (International Ed. in English)
|February 17, 2016
PubMed
Summary

Researchers synthesized a pentane σ-complex using a solid/gas transformation. This complex features unique rhodium-hydrogen-carbon interactions within the crystal lattice, confirmed by X-ray diffraction and spectroscopy.

Keywords:
C−H activationalkanescomputationrhodiumsigma complexes

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Area of Science:

  • Organometallic Chemistry
  • Solid-State Chemistry
  • Computational Chemistry

Background:

  • Synthesis of transition metal-alkane complexes is crucial for understanding C-H activation.
  • Previous studies often involve solution-phase reactions, limiting solid-state insights.
  • The development of single-crystal to single-crystal transformations offers a pathway to study solid-state reactivity.

Purpose of the Study:

  • To synthesize and characterize a pentane σ-complex of rhodium.
  • To investigate the nature of rhodium-alkane interactions in the solid state.
  • To explore the influence of the crystal lattice on alkane coordination and reactivity.

Main Methods:

  • Solid/gas single-crystal to single-crystal transformation of a 1,3-pentadiene precursor.
  • Low-temperature single-crystal X-ray diffraction (150 K) for structural determination.
  • Solid-state Nuclear Magnetic Resonance (SSNMR) spectroscopy (158 K) for dynamic studies.
  • Periodic Density Functional Theory (DFT) calculations and molecular dynamics simulations.

Main Results:

  • Successful synthesis of the pentane σ-complex [Rh{Cy2P(CH2)2PCy2}(η2:η2-C5H12)][BAr(F)4].
  • Characterization revealed coordination via two Rh···H-C interactions at the 2,4-positions of the pentane.
  • DFT and molecular dynamics provided insights into the Rh···H-C interaction and crystal environment.
  • SSNMR data indicated temperature-dependent pentane rearrangement within the solid state.

Conclusions:

  • The study demonstrates a novel solid-state synthesis of a rhodium-pentane σ-complex.
  • Rh···H-C interactions are key to stabilizing the alkane in the solid state.
  • The crystal lattice plays a significant role in mediating alkane dynamics and reactivity.