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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

16.1K
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...
16.1K
Hydrogen Bonds00:26

Hydrogen Bonds

136.3K
Hydrogen 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 unequally shared....
136.3K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
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...
4.3K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.1K
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
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

10.0K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
10.0K
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

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Updated: Mar 26, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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AMHB: (Anti)aromaticity-Modulated Hydrogen Bonding.

Tayeb Kakeshpour1, Judy I Wu2, James E Jackson1

  • 1Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.

Journal of the American Chemical Society
|February 11, 2016
PubMed
Summary
This summary is machine-generated.

This study reveals how altering the aromaticity of π-conjugated heterocycles precisely controls hydrogen bond strength. This aromaticity-modulated H-bonding phenomenon impacts various chemical and biological applications.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Hydrogen bonds are crucial in molecular interactions.
  • Aromaticity influences molecular properties and reactivity.
  • Understanding π-conjugated systems is key in chemistry.

Purpose of the Study:

  • To investigate the relationship between (anti)aromaticity and hydrogen bond strength in π-conjugated heterocycles.
  • To explore how π-electron polarization affects H-bonded complexes.
  • To identify the (anti)aromaticity-modulated H-bonding (AMHB) phenomenon.

Main Methods:

  • In silico computational survey.
  • Analysis of π-electron polarization during H-bonding.
  • Computation of dissected nucleus-independent chemical shifts (NICS(1)(zz)) to assess magnetic aromaticity.

Main Results:

  • Changes in (anti)aromaticity fine-tune hydrogen bond strengths.
  • π-electron polarization during dimerization reinforces or disrupts π-conjugated circuits.
  • H-bonding interactions are strengthened by enhanced aromaticity or relieved antiaromaticity.
  • Interactions intensifying antiaromaticity or disrupting aromaticity are weakened.
  • Computed NICS(1)(zz) values consistently document changes in magnetic (anti)aromatic character.

Conclusions:

  • The (anti)aromaticity-modulated H-bonding (AMHB) phenomenon provides a new perspective on H-bond modulation.
  • This understanding has implications for organocatalysis, self-assembly, and pharmaceutical chemistry.
  • Fine-tuning H-bond strengths via aromaticity offers novel design strategies.