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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
IR Spectrum Peak Broadening: Hydrogen Bonding01:23

IR Spectrum Peak Broadening: Hydrogen Bonding

The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
However, the extent of hydrogen bonding influences the observed stretching frequency and band broadening. Intermolecular or intramolecular hydrogen bonding...
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones.

Diana Becerra1, Braulio Insuasty, Justo Cobo

  • 1Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.

Acta Crystallographica. Section C, Crystal Structure Communications
|February 4, 2010
PubMed
Summary
This summary is machine-generated.

This study investigates the crystal structures of indolin-2-one derivatives. Hydrogen bonding and pi-pi stacking interactions dictate their molecular arrangements in solid-state, revealing diverse supramolecular structures.

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Published on: February 15, 2016

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Indolin-2-one derivatives are important scaffolds in medicinal chemistry.
  • Understanding their solid-state structures is crucial for drug design and material science.
  • Previous studies have explored related compounds, providing a basis for comparison.

Purpose of the Study:

  • To elucidate the crystal structures of racemic 3-benzoylmethyl-3-hydroxyindolin-2-one and its five monosubstituted analogues.
  • To analyze the role of hydrogen bonding and pi-pi stacking in the self-assembly of these molecules.
  • To compare the observed crystal packing with related indolin-2-one derivatives.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular structures and crystal packing.
  • Analysis of hydrogen bonding (N-H...O, O-H...O) and weak interactions (C-H...O, C-H...pi) was performed.
  • Comparison of crystal structures of seven related indolin-2-one compounds.

Main Results:

  • Racemic 3-benzoylmethyl-3-hydroxyindolin-2-one forms chains via N-H...O and O-H...O hydrogen bonds.
  • Five monosubstituted analogues are isomorphous, forming chains and sheets through similar hydrogen bonds and aromatic pi-pi stacking.
  • A thienyl derivative also forms hydrogen-bonded chains, with sheet formation driven by thienyl ring pi-pi stacking.

Conclusions:

  • The crystal structures of indolin-2-one derivatives are dictated by a combination of hydrogen bonding and pi-pi stacking interactions.
  • Substituents on the benzoyl group influence the specific hydrogen bonding patterns and overall supramolecular architecture.
  • These findings contribute to the understanding of structure-property relationships in this class of compounds.