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Hydrogen Bonds00:26

Hydrogen Bonds

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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....
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Hydrogen Bonds01:04

Hydrogen Bonds

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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...
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IR Spectrum Peak Broadening: Hydrogen Bonding01:23

IR Spectrum Peak Broadening: Hydrogen Bonding

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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...
1.8K
Valence Bond Theory02:45

Valence Bond Theory

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Overview of Valence Bond Theory
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Covalent Bonds01:29

Covalent Bonds

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Overview
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Chirality02:25

Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Updated: Jan 28, 2026

A Micropatterning Assay for Measuring Cell Chirality
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Chiral Superbases with Extended Hydrogen Bond Networks.

Steven M Bachrach1

  • 1Department of Chemistry and School of Science , Monmouth University , 400 Cedar Avenue , West Long Branch , New Jersey 07764 , United States.

The Journal of Organic Chemistry
|February 23, 2019
PubMed
Summary
This summary is machine-generated.

Chiral superbases with anilinyl groups show tunable basicity and can induce enantioselectivity in deprotonation reactions. These compounds offer potential for asymmetric synthesis applications.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Extended hydrogen bond networks enhance basicity by stabilizing conjugate acids.
  • 1,8-bis(dimethylamino)naphthalene is a prototype superbase.

Purpose of the Study:

  • To investigate the basicity and enantioselectivity of novel chiral superbases.
  • To explore the effect of anilinyl substituents on the properties of 1,8-bis(dimethylamino)naphthalene.

Main Methods:

  • Density Functional Theory (DFT) methods, specifically PBE1PBE/6-311+G(d,p), were employed.
  • Computational analysis of chiral superbases (9-11) with anilinyl substituents.

Main Results:

  • Chiral superbases 9-11 exhibit higher basicity in the gas phase but lower basicity in THF solution compared to the parent superbase 1.
  • A significant rotational barrier (approx. 20 kcal mol⁻¹) was observed around the Caryl-Caryl bond in chiral superbases 9-11.
  • Aminonaphthyl substituents increased this rotational barrier by approximately 10 kcal mol⁻¹.
  • Predicted enantiomeric excesses (ee's) for deprotonation of propanal ranged from 58% to 95% using chiral bases 9-11.
  • Deprotonation of 4-tert-butylcyclohexanone and cyclohexanoxide by base 9 yielded ee's of 23% and 97%, respectively.

Conclusions:

  • The designed chiral superbases demonstrate tunable basicity and potential for enantioselective deprotonation.
  • These findings highlight the utility of these chiral superbases as catalysts in asymmetric synthesis.