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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.1K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

2.0K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
2.0K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.9K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.9K
π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

1.9K
An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0,...
1.9K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.6K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...
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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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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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Different N-H⋯π inter-actions in two indole derivatives.

Jamie R Kerr1, Laurent Trembleau1, John M D Storey1

  • 1Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.

Acta Crystallographica. Section E, Crystallographic Communications
|June 17, 2016
PubMed
Summary

This study details the synthesis and crystal structures of two novel indole derivatives. The research reveals that N-H⋯π bonds, not hydrogen bonds, are the primary intermolecular forces driving crystal packing in these compounds.

Keywords:
N—H⋯π inter­actionchainscrystal structureindoleinversion dimers

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Spatial Separation of Molecular Conformers and Clusters
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Spatial Separation of Molecular Conformers and Clusters
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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Indole derivatives are important scaffolds in medicinal chemistry.
  • Understanding intermolecular interactions is crucial for crystal engineering and material design.

Purpose of the Study:

  • To synthesize and characterize two novel indole derivatives.
  • To elucidate the crystal structures and dominant intermolecular interactions of these compounds.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Structural analysis of intermolecular interactions (N-H⋯π, C-H⋯π, π-π stacking).

Main Results:

  • The crystal structures of 6-isopropyl-3-(2-nitro-1-phenyl-eth-yl)-1H-indole and 2-(4-meth-oxy-phen-yl)-3-(2-nitro-1-phenyl-eth-yl)-1H-indole were determined.
  • N-H⋯π bonds were identified as the dominant intermolecular interactions, leading to distinct packing motifs (chains and inversion dimers).
  • C-H⋯π interactions contribute to crystal consolidation, while π-π stacking interactions are absent.

Conclusions:

  • The study highlights the significant role of N-H⋯π interactions in the crystal packing of these indole derivatives.
  • The findings provide insights into the structure-property relationships of indole-based compounds and inform crystal engineering strategies.