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Related Concept Videos

Amino acids03:42

Amino acids

Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered ethane, the...
Conformations of Butane02:20

Conformations of Butane

Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are degenerate and have...
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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Related Experiment Video

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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
07:26

Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides

Published on: November 21, 2013

The shape of beta-alanine.

M Eugenia Sanz1, Alberto Lesarri, M Isabel Peña

  • 1Grupo de Espectroscopía Molecular, Departamento de Química Física y Química Inorganica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain.

Journal of the American Chemical Society
|March 16, 2006
PubMed
Summary

Researchers identified four beta-alanine conformers using microwave spectroscopy. Two new structures were discovered, including one stabilized by a unique n-pi* hyperconjugative interaction, offering insights into molecular structure.

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Area of Science:

  • Physical Chemistry
  • Molecular Spectroscopy
  • Computational Chemistry

Background:

  • Beta-alanine is an important amino acid with limited gas-phase structural data.
  • Previous studies identified two conformers of beta-alanine.

Purpose of the Study:

  • To investigate the gas-phase structure of beta-alanine.
  • To identify and characterize novel conformers of beta-alanine.

Main Methods:

  • Fourier transform microwave spectroscopy
  • Pulsed supersonic jet expansion
  • Laser ablation
  • Ab initio calculations

Main Results:

  • Four conformers of beta-alanine were identified in the gas phase.
  • Two new conformers were discovered, including one stabilized by n-pi* hyperconjugation.
  • Experimental data confirmed theoretical calculations for all identified conformers.
  • Intramolecular hydrogen bonding (N-H...O=C or O-H...N) and COOH configurations (cis/trans) were determined.

Conclusions:

  • The study provides a definitive structural characterization of beta-alanine conformers in the gas phase.
  • The discovery of an n-pi* stabilized conformer highlights novel intermolecular interactions.
  • Observed conformational relaxation provides insights into supersonic expansion dynamics.