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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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.
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Structural Isomerism

Isomerism in Complexes
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Crystallization is a phase transformation process in which crystals are precipitated from a supersaturated solution or formed from other sources. During crystallization, atoms or molecules arrange themselves into a well-defined, rigid crystal lattice to minimize energy.
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Recrystallization: Solid–Solution Equilibria01:10

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Recrystallization is a purification technique used to separate impurities from solid compounds. In this technique, no chemical reactions occur. Instead, it exploits physical properties only, specifically, the solubility differences between the desired compound and impurities, either at a single temperature or at different temperatures, and under other selected conditions. The solid-solution equilibrium (solubility equilibrium) of each component in the solution represents a binary phase...
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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...

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Optimization of Crystal Growth for Neutron Macromolecular Crystallography
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Cyanoximes as effective and selective co-crystallizing agents.

Christer B Aakeröy1, Debra J Salmon, Michelle M Smith

  • 1Department of Chemistry, Kansas State University, Manhattan, KS, 66506, aakeroy@ksu.edu.

Crystengcomm
|January 5, 2010
PubMed
Summary
This summary is machine-generated.

Cyanoxime synthons are versatile tools for creating co-crystals. They effectively bind to N-heterocyclic acceptors, showing selectivity for stronger binding sites in complex molecules.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Crystallography

Background:

  • Co-crystals are crystalline solids composed of two or more molecular components held together by non-covalent interactions.
  • Cyanoximes are organic compounds containing the C=N-OH functional group, which can participate in hydrogen bonding.
  • Designing co-crystals with specific properties requires understanding the interactions between molecular components.

Purpose of the Study:

  • To demonstrate the utility of cyanoxime-based synthons in constructing co-crystals.
  • To structurally characterize novel co-crystals formed using cyanoximes.
  • To investigate the hydrogen bonding capabilities and selectivity of cyanoximes with N-heterocyclic acceptors.

Main Methods:

  • Synthesis of seven co-crystals utilizing cyanoxime synthons.
  • Single-crystal X-ray diffraction for structural characterization of the co-crystals.
  • Semi-empirical AM1 calculations to predict and analyze hydrogen bond acceptor strengths.

Main Results:

  • Successful preparation and structural elucidation of seven distinct co-crystals.
  • Demonstrated effective binding of cyanoximes to both five-membered and six-membered N-heterocyclic hydrogen-bond acceptors.
  • Observed selectivity of cyanoximes towards the strongest hydrogen-bond acceptor in ditopic systems, consistent with computational predictions.

Conclusions:

  • Cyanoxime-based synthons are effective and versatile building blocks for co-crystal engineering.
  • The hydrogen bonding behavior of cyanoximes can be predicted and controlled, enabling rational design of co-crystals.
  • This work expands the toolkit for supramolecular chemists seeking to create novel crystalline materials.