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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 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.
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 II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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 π orbitals.
Introduction to Chemical Bonds01:01

Introduction to Chemical Bonds

Chemical Bonds
The electrons of the outermost energy level determine the energetic stability of the atom and its tendency to form chemical bonds with other atoms. The innermost electron shell has a maximum capacity of two electrons, but the next two electron shells can each have a maximum of eight electrons. This is known as the octet rule, which states that, with the exception of the innermost shell, atoms are most stable energetically when they have eight electrons in their valence shell, the...

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Extended hydrogen bond network enabled superbases.

Steven M Bachrach1

  • 1Department of Chemistry, Trinity University, One Trinity Place, San Antonio, Texas 78212, USA. sbachrach@trinity.edu

Organic Letters
|October 18, 2012
PubMed
Summary
This summary is machine-generated.

Researchers developed new organic superbases with enhanced hydrogen-bonding networks, significantly increasing their basicity compared to proton sponge. These novel compounds show potential for advanced chemical applications.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Proton sponge is a well-known strong organic base.
  • Developing new superbases with enhanced properties is an active area of research.
  • Hydrogen-bonding networks play a crucial role in molecular interactions and properties.

Purpose of the Study:

  • To design and investigate novel organic superbases.
  • To explore the role of extended hydrogen-bonding networks in enhancing basicity.
  • To compare the basicity of new compounds with that of proton sponge.

Main Methods:

  • Computational chemistry, specifically Density Functional Theory (DFT) calculations.
  • Design of organic compounds based on the 1,8-diaminonaphthalene framework.
  • Introduction of aminoethyl and related groups to create multi-layer hydrogen bonding.

Main Results:

  • New superbases incorporating extended hydrogen-bonding networks were proposed.
  • The addition of specific functional groups facilitated second- and third-layer hydrogen bonding in the conjugate base.
  • DFT computations predicted these novel compounds to be 10-15 kcal mol(-1) more basic than proton sponge.

Conclusions:

  • Extended hydrogen-bonding networks are effective in creating highly basic organic compounds.
  • The designed superbases represent a significant advancement in basicity beyond proton sponge.
  • These findings open avenues for the development of new reagents in organic synthesis and catalysis.