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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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1,5-Bis(1-phenyl-ethyl-idene)carbonohydrazide.

Lingqian Kong1, Yan Qiao, Zhiqing Gao

  • 1Dongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

This study details the crystal structure of a molecule with formula C(17)H(18)N(4)O. It reveals specific dihedral angles between phenyl rings and intermolecular hydrogen bonding that form dimers and chains.

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Area of Science:

  • Crystallography
  • Molecular Structure
  • Supramolecular Chemistry

Background:

  • Understanding molecular interactions is crucial in chemistry.
  • Crystal structure analysis provides insights into intermolecular forces.

Purpose of the Study:

  • To determine the crystal structure of the molecule C(17)H(18)N(4)O.
  • To investigate the intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed.
  • Analysis of bond lengths, angles, and intermolecular contacts was performed.

Main Results:

  • The molecule C(17)H(18)N(4)O exhibits a dihedral angle of 18.15° between its two phenyl rings.
  • Intermolecular N-H⋯O hydrogen bonds form centrosymmetric dimers.
  • Weak C-H⋯O interactions further assemble these dimers into chains along the [010] direction.

Conclusions:

  • The crystal packing is governed by a combination of hydrogen bonding and weaker interactions.
  • The identified structural motifs provide a basis for understanding the solid-state properties of this compound.