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Structures of Carboxylic Acid Derivatives01:28

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Anionic and zwitterionic carboranyl N-heterocyclic carbene Au(i) complexes.

Steven P Fisher1, Ahmad El-Hellani2, Fook S Tham1

  • 1Department of Chemistry University of California Riverside, Riverside, CA 92521, USA. vincent.lavallo@ucr.edu.

Dalton Transactions (Cambridge, England : 2003)
|March 1, 2016
PubMed
Summary

Researchers synthesized novel carboranyl N-heterocyclic carbene (NHC) complexes with gold. These new gold-NHC compounds exhibit unique structures and increased steric bulk compared to traditional adamantyl NHCs.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Carboranes are unique boron-rich clusters with diverse applications.
  • The development of novel NHC ligands is crucial for advancing catalysis and materials science.

Purpose of the Study:

  • To report the synthesis of the first carboranyl N-heterocyclic carbene (NHC) complexes.
  • To investigate the reactivity of these novel NHCs with gold precursors.
  • To characterize the resulting gold-NHC adducts and evaluate their structural properties.

Main Methods:

  • Synthesis of unsymmetrical mono-anionic and symmetrical dianionic carboranyl NHCs.
  • Reaction of NHCs with chloro(dimethyl sulfide)gold(I) (ClAuSMe2).
  • Characterization using NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction.
  • Calculation of percent buried volume (%Vbur) to assess steric properties.

Main Results:

  • Successful synthesis of novel carboranyl NHC ligands.
  • Formation of unusual zwitterionic and anionic gold(I) dimethyl sulfide adducts.
  • X-ray diffraction confirmed the structures of the synthesized compounds.
  • Replacement of adamantyl groups with carborane moieties increased steric bulk by 3.7% (%Vbur).

Conclusions:

  • The first carboranyl NHC-metal complexes have been successfully synthesized.
  • These novel NHCs form unique gold(I) adducts with significant steric profiles.
  • The increased %Vbur suggests potential for enhanced stability or altered reactivity in catalytic applications.