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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

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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.
Due to the absence of continuous...
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IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

7.2K
Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
7.2K
α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Structure and Nomenclature of Epoxides02:38

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Summary
This summary is machine-generated.

Structural analysis of a novel coumarin derivative reveals a significant dihedral angle between its core components. Molecular interactions, including hydrogen bonds and pi-pi stacking, dictate crystal packing and stability.

Keywords:
Hirshfeld surfacecoumarinscrystal structurehydrogen bond

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Coumarin derivatives are known for diverse biological activities.
  • Understanding molecular structure and intermolecular interactions is crucial for designing new materials.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a novel coumarin derivative (C14H14O4).
  • To analyze the factors contributing to the compound's crystal cohesion.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Hirshfeld surface analysis was used to quantify intermolecular interactions.

Main Results:

  • The coumarin nucleus was found to be planar.
  • A dihedral angle of 62.20(7)° was observed between the coumarin and penta-noate moieties.
  • Centrosymmetric dimers linked by C-H⋯O hydrogen bonds and π-π interactions were identified.
  • Hirshfeld surface analysis indicated H⋯H contacts (44.6%) as the dominant intermolecular interaction, followed by O⋯O/O⋯H (28.2%) and H⋯C/C⋯H (16.3%) contacts.

Conclusions:

  • The crystal structure is stabilized by a combination of hydrogen bonding and π-π interactions.
  • Hirshfeld surface analysis provides detailed insights into the nature and proportion of intermolecular forces governing crystal packing.