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Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

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Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...
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Structure of Alkanes02:23

Structure of Alkanes

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The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes. 
Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms....
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Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

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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.
The...
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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Electrophilic Addition to Alkynes: Halogenation02:38

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

Mass Spectrometry: Long-Chain Alkane Fragmentation

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The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
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Characterisation of alkane σ-complexes.

Rowan D Young1

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 (Singapore). rowan.young@nus.edu.sg.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 9, 2014
PubMed
Summary
This summary is machine-generated.

Metal alkane σ-complexes are increasingly studied. This review details their bonding metrics, binding modes, selectivity, and stability, advancing understanding of these intermediates.

Keywords:
CH activationalkanescoordination modesrhenium

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Chemical Bonding

Background:

  • Alkane σ-complexes have transitioned from curiosities to key intermediates in chemical research.
  • Historically, geometric characterization was limited, leading to assumptions based on related complexes or C-H activation products.

Purpose of the Study:

  • To review and illuminate the bonding metrics of alkane-metal bonds.
  • To critically analyze the binding modes, selectivity, and stability of metal alkane complexes.

Main Methods:

  • Literature review of studies employing UV/Vis, IR, NMR spectroscopy, and X-ray and neutron diffractometry.
  • Assembly of data illuminating alkane-metal bonding metrics.
  • Critical analysis of binding characteristics.

Main Results:

  • Detailed characterization of metal alkane complexes has advanced significantly over the past fifteen years.
  • Established metrics for alkane-metal bonding are now available.
  • Insights into binding modes, selectivity, and stability have been elucidated.

Conclusions:

  • The understanding of metal alkane σ-complexes has matured due to advanced characterization techniques.
  • This review provides a critical analysis of their bonding, selectivity, and stability.
  • Further research is fueled by the growing interest in these important chemical intermediates.