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Related Concept Videos

Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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...
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...

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Interactive Molecular Model Assembly with 3D Printing
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Conformational cooling dynamics in matrix-isolated 1,3-butanediol.

Mário T S Rosado1, António J Lopes Jesus, Igor D Reva

  • 1Department of Chemistry, University of Coimbra, 3004-535, Coimbra, Portugal. mtulio@qui.uc.pt

The Journal of Physical Chemistry. A
|April 25, 2009
PubMed
Summary

Theoretical calculations reveal 73 stable conformers of 1,3-butanediol, classifying them into nine families. Experimental infrared spectra analysis confirms conformational cooling dynamics, with agreement between theoretical and experimental results.

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Area of Science:

  • Computational chemistry
  • Molecular spectroscopy
  • Physical chemistry

Background:

  • Understanding molecular conformation is crucial for predicting chemical properties and reactivity.
  • Previous studies on 1,3-butanediol conformation have overlooked certain stable families.
  • Intramolecular hydrogen bonding plays a significant role in stabilizing specific conformers.

Purpose of the Study:

  • To comprehensively characterize the conformational landscape of monomeric 1,3-butanediol.
  • To investigate the role of intramolecular hydrogen bonding in conformational stability.
  • To correlate theoretical predictions with experimental observations of conformational dynamics.

Main Methods:

  • Ab initio calculations (MP2/6-311++G(d,p)) to determine stable conformers and transition states.
  • Atoms in Molecules (AIM) and Natural Bond Orbital (NBO) analyses for hydrogen bond characterization.
  • Infrared spectroscopy of matrix-isolated 1,3-butanediol to study conformational distribution.

Main Results:

  • Identified 73 unique stable conformers, grouped into nine families based on backbone configuration.
  • Quantified hydrogen bond stabilization energies between 12-14 kJ mol(-1).
  • Observed and explained conformational cooling dynamics in low-temperature inert matrices, consistent with calculated energy barriers.

Conclusions:

  • The study provides a complete theoretical characterization of 1,3-butanediol conformers, including previously overlooked families.
  • Experimental data validates theoretical predictions regarding conformational stability and interconversion dynamics.
  • Intramolecular hydrogen bonding and entropic effects govern the conformational preferences of 1,3-butanediol.