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Related Concept Videos

Leveling Effect01:29

Leveling Effect

In acid-base chemistry, the leveling effect refers to the limitation imposed by the solvent on the strength of acids and bases in solution. When a base stronger than the solvent's conjugate base is used, it deprotonates the solvent until the base is entirely consumed, making it ineffective against weaker acids. Conversely, an acid stronger than the solvent's conjugate acid protonates the solvent until the acid is depleted, rendering it ineffective against weaker bases. Essentially, the solvent...
Solvating Effects02:12

Solvating Effects

An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

Leveling Effect and Non-Aqueous Acid-Base Solutions

This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Phosphodiester Linkages01:01

Phosphodiester Linkages

Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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.

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Related Experiment Video

Updated: May 18, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Hyperconjugation-mediated solvent effects in phosphoanhydride bonds.

Jean C Summerton1, Jeffrey D Evanseck, Michael S Chapman

  • 1Department of Biochemistry & Molecular Biology, School of Medicine, Oregon Health & Science University, Mail Code L224, 3181 SW Sam Jackson Park Road, Portland, Oregon 97239-3098, USA.

The Journal of Physical Chemistry. A
|September 27, 2012
PubMed
Summary

Solvent interactions significantly impact hyperconjugation in methyl triphosphate, a model for ATP's energy-rich bonds. Water coordination modulates the anomeric effect, influencing phosphoanhydride bond stability through stereoelectronic effects.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Related Experiment Videos

Last Updated: May 18, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

  • Computational Chemistry
  • Biochemistry
  • Molecular Modeling

Background:

  • Phosphoanhydride bonds, like those in ATP, are crucial for cellular energy.
  • Understanding the factors influencing their stability is key to metabolic and signaling research.

Purpose of the Study:

  • To investigate the influence of solvent on hyperconjugation in methyl triphosphate.
  • To elucidate the stereoelectronic mechanisms by which solvents modulate phosphoanhydride bond stability.

Main Methods:

  • Density functional theory (DFT) calculations.
  • Natural bond orbital (NBO) analysis.
  • Modeling of methyl triphosphate in various solvent environments.

Main Results:

  • Solvent hydrogen bonds, both gauche and anti, reduce the anomeric effect by lengthening nonbridging O-P bonds.
  • Increased water coordination leads to an additive reduction in the anomeric effect.
  • Conformational changes of solvent hydrogen bonds influence orbital overlap and anomeric effect magnitude.

Conclusions:

  • Enzymes can potentially tune phosphoanhydride bond stability by controlling the substrate's coordination environment.
  • Stereoelectronic effects mediated by solvent interactions play a significant role in modulating the strength of energy-rich bonds.