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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.
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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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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
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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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Anion-Carbonyl Interactions.

Jun Zhu1, De-Hui Tuo1, Xu-Dong Wang1

  • 1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Organic Letters
|July 8, 2024
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Summary

This study reveals a novel non-covalent anion-carbonyl interaction using aromatic imides. Experimental and theoretical methods confirm electrostatic forces and electron delocalization drive this significant binding interaction.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Non-covalent interactions are crucial in molecular recognition and self-assembly.
  • Anion-carbonyl interactions represent an important class of non-covalent forces.

Purpose of the Study:

  • To explore and characterize a novel non-covalent anion-carbonyl interaction.
  • To elucidate the physical origin and provide experimental evidence for these interactions.

Main Methods:

  • Theoretical calculations including Density Functional Theory (DFT) and Energy Decomposition Analysis (EDA).
  • Experimental techniques such as Carbon-13 Nuclear Magnetic Resonance (13C NMR) and Infrared (IR) spectroscopy.
  • X-ray crystallographic analysis of anion and benzene triimide complexes.

Main Results:

  • DFT calculations indicated that electrostatic contributions dominate the binding energy, with significant electron delocalization.
  • Natural Bond Orbital (NBO) analysis visualized orbital interactions (n → π*) between halide lone pairs and carbonyl antibonding orbitals.
  • Spectroscopic data (13C NMR and IR) showed characteristic shifts and frequency changes upon halide addition, confirming the interaction.

Conclusions:

  • The study provides comprehensive evidence for a novel anion-carbonyl interaction.
  • Both electrostatic attraction and electron delocalization contribute significantly to the binding energy.
  • This interaction has implications for the design of novel receptors and anion sensing systems.