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Related Concept Videos

Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

24.1K
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...
24.1K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

3.0K
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...
3.0K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

12.1K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
12.1K
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

15.0K
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...
15.0K
Isomerism in Alkenes02:01

Isomerism in Alkenes

16.6K
Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
16.6K
Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

16.4K
The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
16.4K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Surfing π clouds for noncovalent interactions: arenes versus alkenes.

Abil E Aliev1, Josephine R T Arendorf, Ilias Pavlakos

  • 1Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ (UK). a.e.aliev@ucl.ac.uk.

Angewandte Chemie (International Ed. in English)
|November 19, 2014
PubMed
Summary

Noncovalent interactions with arenes are stronger than with alkenes, with cyano groups showing the strongest interaction. These π-interactions are electrostatic and depend on solvent properties.

Keywords:
NMR spectroscopyconformational analysismolecular balancesnoncovalent interactionsπ interactions

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • Understanding noncovalent interactions is crucial in chemistry.
  • Arene and alkene interactions with functional groups are key to molecular recognition.
  • Intramolecular hydrogen bonding influences molecular conformation.

Purpose of the Study:

  • To compare noncovalent interactions of functional groups with arenes and alkenes.
  • To investigate the strength and nature of π-facial intramolecular hydrogen bonds.
  • To correlate conformational free-energy differences with substituent properties and solvent effects.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy was used for comparative analysis.
  • Computational methods were employed to calculate atomic charges.
  • Analysis of conformational free-energy differences was performed.

Main Results:

  • Noncovalent interactions with arenes dominate over alkenes.
  • A π-facial intramolecular hydrogen bond from a hydroxyl group to an arene is favored by ~1.2 kJ/mol.
  • The cyano group exhibited the strongest observed interaction.
  • A correlation was found between conformational free-energy differences and the calculated charge on the C(α) atom.
  • Changes in free-energy differences showed a linear dependence on the solvent hydrogen bond acceptor parameter (β).

Conclusions:

  • Electrostatic forces are significant in π-interactions between substituents and aromatic rings.
  • The strength of these interactions is influenced by the electronic properties of the substituent and the solvent environment.
  • NMR spectroscopy provides valuable insights into noncovalent interactions and molecular conformation.