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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Synthesis and Exfoliation of Discotic Zirconium Phosphates to Obtain Colloidal Liquid Crystals
08:54

Synthesis and Exfoliation of Discotic Zirconium Phosphates to Obtain Colloidal Liquid Crystals

Published on: May 25, 2016

En route to zirconium hydrazides(2-).

Heike Herrmann1, Hubert Wadepohl, Lutz H Gade

  • 1Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Dalton Transactions (Cambridge, England : 2003)
|April 10, 2008
PubMed
Summary

New zirconium hydrazido(1-) complexes were synthesized and characterized. Conversion to hydrazido(2-) species proved challenging, dependent on N beta-substituents and co-ligands for stable zirconium complexes.

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Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Zirconium Complexes

Background:

  • Zirconium complexes are crucial in catalysis and materials science.
  • Understanding the reactivity of hydrazido ligands is key to developing new synthetic methodologies.
  • Previous studies on zirconium hydrazido complexes are limited, particularly concerning their conversion to higher oxidation states.

Purpose of the Study:

  • To synthesize and characterize novel zirconium hydrazido(1-) complexes.
  • To investigate the feasibility of converting these hydrazido(1-) complexes to hydrazido(2-) species.
  • To explore the influence of ligand substituents and co-ligands on the stability and isolation of zirconium hydrazido complexes.

Main Methods:

  • Synthesis of zirconium hydrazido(1-) complexes via reaction of [Zr(N2TBSNpy)Cl2] with lithiated hydrazides.
  • Attempts at conversion to hydrazido(2-) complexes using strong bases (lithium hexamethyldisilazide) and thermal elimination.
  • Characterization using spectroscopic techniques (NMR, IR) and elemental analysis.

Main Results:

  • Successfully synthesized two isomeric forms of a zirconium hydrazido(1-) complex, [Zr(N2TBSNpy)(NHNMe2)Cl].
  • Conversion attempts to the corresponding hydrazido(2-) complex were unsuccessful.
  • Synthesized a zirconium hydrazido(2-) complex, [Zr(N2TBSNpy)(NNPhMe)(dmap)], which was fully characterized, demonstrating that N beta-substituents and co-ligands are critical for stability.

Conclusions:

  • The successful isolation of stable zirconium hydrazido(2-) complexes is highly dependent on the nature of the substituents on the nitrogen beta atom.
  • The choice of co-ligands, such as 4-dimethylaminopyridine (dmap), plays a crucial role in stabilizing the hydrazido(2-) species.
  • This study provides insights into the synthetic challenges and requirements for accessing diverse zirconium hydrazido complexes.