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Related Concept Videos

Conformations of Butane02:20

Conformations of Butane

15.6K
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...
15.6K
Structural Isomerism02:34

Structural Isomerism

19.9K
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
19.9K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.2K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.2K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

2.9K
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...
2.9K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.5K
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...
13.5K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.0K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
10.0K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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A liquid with distinct metastable structures: Supercooled butyronitrile.

Jan P Gabriel1, Erik Thoms1, A Guiseppi-Elie2

  • 1School of Molecular Sciences, Arizona State University, Tempe, Arizona 85287-1604, USA.

The Journal of Chemical Physics
|February 2, 2022
PubMed
Summary

Dielectric properties of butyronitrile were studied in bulk and vapor-deposited forms. Bulk samples show a higher dielectric constant, suggesting cluster formation influencing molecular glass behavior.

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Area of Science:

  • Materials Science
  • Physical Chemistry
  • Condensed Matter Physics

Background:

  • Molecular glasses exhibit complex dielectric relaxation behaviors.
  • Butyronitrile is a model molecular glass former.
  • Previous studies on butyronitrile's dielectric properties may not capture the full picture.

Purpose of the Study:

  • To re-examine the dielectric relaxation behavior of butyronitrile.
  • To compare dielectric properties of bulk and vapor-deposited samples.
  • To understand the influence of sample preparation on molecular glass dynamics.

Main Methods:

  • Dielectric spectroscopy was performed on bulk butyronitrile cooled from the melt.
  • Dielectric measurements were conducted on butyronitrile samples prepared by physical vapor deposition.
  • Varying deposition temperature and rate for vapor-deposited samples.

Main Results:

  • Bulk liquid butyronitrile exhibits a significantly higher dielectric constant (εs = 63) near its glass transition temperature (Tg = 97 K).
  • Vapor-deposited samples show a range of dielectric constants (4.5–63) depending on preparation conditions.
  • Low dielectric constant values in vapor-deposited samples persist for extended periods, with relaxation times around 0.1 s.

Conclusions:

  • The formation of long-lived, non-crystalline clusters with anti-parallel dipole orientation explains the observed dielectric behavior.
  • These clusters persist above the glass transition temperature, coexisting with the equilibrium polar liquid fraction.
  • Sample preparation methods critically influence the dielectric response and structure of molecular glasses like butyronitrile.