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Packing effects in 4,4'-bis(4-hydroxybutyl)-2,2'-bipyridine and 4,4'-bis(4-bromobutyl)-2,2'-bipyridine

Vijay Mahadevan Iyer1, Helen Stoeckli-Evans, Anthony D'Aléo

  • 1Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700 Fribourg, Switzerland. vijaymahadevan.iyer@unifr.ch

Acta Crystallographica. Section C, Crystal Structure Communications
|April 5, 2005
PubMed

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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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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...
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