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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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 π orbitals.
π Molecular Orbitals of the Allyl Cation and Anion01:18

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...
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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons.
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Supramolecular architectures based on As(lone pair)···π(aryl) interactions.

Julio Zukerman-Schpector1, Alberto Otero-de-la-Roza, Víctor Luaña

  • 1Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P. 676, São Carlos, SP 13565-905, Brazil. julio@power.ufscar.br

Chemical Communications (Cambridge, England)
|May 10, 2011
PubMed
Summary

Arsenic lone pair-π interactions stabilize crystal structures, forming supramolecular chains. These interactions are stronger than other arsenic contacts, driven by electron sharing and polarization.

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Organometallic Chemistry

Background:

  • Non-covalent interactions are crucial for crystal structure assembly.
  • Arsenic-containing compounds exhibit diverse intermolecular interactions.
  • Understanding these interactions guides the design of novel materials.

Purpose of the Study:

  • To investigate the role of arsenic lone pair (As)···π interactions in stabilizing crystal structures.
  • To quantify the strength and nature of these interactions.
  • To compare As···π interactions with other secondary arsenic contacts.

Main Methods:

  • Crystallographic analysis of arsenic-containing compounds.
  • Computational chemistry methods to analyze electronic interactions.
  • Energy calculations to quantify interaction strengths.

Main Results:

  • As(lone pair)···π interactions were identified as a significant stabilizing force in crystal structures.
  • These interactions lead to the formation of supramolecular chains.
  • The strength of the As···π interaction was quantified at approximately 8 kJ mol(-1).
  • As···π interactions were found to be dominant over other As···X secondary contacts.

Conclusions:

  • As(lone pair)···π interactions play a key role in the self-assembly of arsenic-containing molecules.
  • These interactions contribute to the formation of ordered supramolecular architectures.
  • The findings provide insights into the design principles for crystal engineering with arsenic compounds.