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Related Concept Videos

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.
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...
DNA Base Pairing02:27

DNA Base Pairing

Erwin Chargaff’s rules on DNA equivalence paved the way for the discovery of base pairing in DNA. Chargaff’s rules state that in a double-stranded DNA molecule,
DNA Base Pairing02:27

DNA Base Pairing

Erwin Chargaff’s rules on DNA equivalence paved the way for the discovery of base pairing in DNA. Chargaff’s rules state that in a double-stranded DNA molecule,
The DNA Helix01:16

The DNA Helix

Overview
The DNA Helix01:07

The DNA Helix

Deoxyribonucleic acid, or DNA, is the genetic material responsible for passing traits from generation to generation in all organisms and most viruses. DNA is composed of two strands of nucleotides that wind around each other to form a spring-like structure called a double helix. However, the double helix is not perfectly symmetrical. Instead, there are regularly occurring grooves in the structure. The major groove occurs where the sugar-phosphate backbones are relatively far apart. This space...

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Related Experiment Video

Updated: May 24, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Halogen bonding in DNA base pairs.

Anna J Parker1, John Stewart, Kelling J Donald

  • 1Department of Chemistry, Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, United States.

Journal of the American Chemical Society
|February 28, 2012
PubMed
Summary
This summary is machine-generated.

Halogen bonding offers a novel approach to designing artificial DNA base pairs. Bromine-substituted nucleosides show stable structures comparable to natural hydrogen-bonded pairs.

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Molecular Biology

Background:

  • Halogen bonding (R-X···Y) is analogous to hydrogen bonding.
  • It has potential applications in designing artificial proteins and nucleotides.

Purpose of the Study:

  • To explore halogen-bonded DNA base pairs with modified nucleosides.
  • To compare the structures and stabilities of these halogenated systems with natural base pairs.

Main Methods:

  • Computational analysis of halogenated guanine, cytosine, adenine, and thymine nucleosides.
  • Comparison of energetic stability and structural coplanarity.

Main Results:

  • Stable, coplanar structures were identified for most halogenated base pairs.
  • Stability of halogenated pairs was within 2 kcal mol(-1) of hydrogen-bonded analogues.
  • Bromine (Br) showed the best balance of polarizability and steric suitability among halogens (Cl, Br, I).
  • Single substitution of a hydrogen bond for a halogen bond in dA:dT and dG:dC pairs yielded the most stable structures.

Conclusions:

  • Halogen bonding can be effectively used to create stable artificial DNA base pairs.
  • Bromine is the most promising halogen for such applications due to its properties.
  • These findings support the rational design of novel nucleic acid structures.