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Molecular Models02:00

Molecular Models

Physical models representing molecular architectures of chemical compounds play essential roles in understanding chemistry. The use of molecular models makes it easier to visualize the structures and shapes of atoms and molecules.
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Weak Acid Solutions

Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...
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Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Acid Strength and Molecular Structure03:05

Acid Strength and Molecular Structure

Binary Acids and Bases
In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing...
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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
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Related Experiment Video

Updated: Jul 19, 2026

Determination of the Gas-phase Acidities of Oligopeptides
11:00

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Solution and solid-state models of peptide CH...O hydrogen bonds.

Paul W Baures1, Alicia M Beatty, Muthu Dhanasekaran

  • 1Department of Chemistry, 111 Willard Hall, Kansas State University, Manhattan, Kansas 66506, USA. baures@signaturebio.com

Journal of the American Chemical Society
|September 19, 2002
PubMed
Summary

This study demonstrates that CH...O interactions occur concurrently with NH...O hydrogen bonds in fumaramide derivatives, both in solution and solid states. These findings provide valuable models for understanding similar interactions in peptide and protein structures.

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Area of Science:

  • Chemical Physics
  • Molecular Biology
  • Crystallography

Background:

  • Non-covalent interactions, particularly hydrogen bonds, are crucial for molecular structure and function.
  • CH...O interactions, while weaker than traditional N-H...O bonds, play a significant role in stabilizing peptide and protein conformations.
  • Fumaramide derivatives serve as model compounds to investigate these interactions.

Purpose of the Study:

  • To characterize the formation of CH...O interactions in fumaramide derivatives.
  • To compare these interactions in solution and solid states.
  • To establish fumaramide derivatives as models for CH...O interactions in peptide and protein structures.

Main Methods:

  • Solution analysis using 1H Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Solid-state analysis using X-ray crystallography.
  • Titration experiments with deuterated dimethyl sulfoxide (DMSO-d6) in chloroform-d (CDCl3).

Main Results:

  • 1H NMR spectroscopy revealed downfield chemical shifts for CH groups involved in CH...O=S(CD3)2 hydrogen bonds, concurrent with NH...O=S(CD3)2 hydrogen bonding.
  • Non-participating CH groups showed minimal chemical shift changes or upfield shifts at higher DMSO-d6 concentrations.
  • X-ray crystal structures confirmed the presence of CH...O=C hydrogen bonds alongside intermolecular NH...O=C hydrogen bonding.

Conclusions:

  • Both solution NMR and solid-state crystallography provide evidence for concurrent CH...O and NH...O hydrogen bonding in fumaramide derivatives.
  • The observed CH...O=C hydrogen bonds in crystal structures resemble those found in antiparallel beta-sheet structures of proteins.
  • Fumaramide derivatives effectively model CH...O interactions relevant to peptide and protein structural stability.