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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

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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.
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IR and UV–Vis Spectroscopy of Aldehydes and Ketones01:29

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Infrared spectroscopy, also known as vibrational spectroscopy, is mainly used to determine the types of bonds and functional groups in molecules. In aldehydes and ketones, the carbonyl (C=O) bond shows an absorption around 1710 cm-1. The C=O bond vibration of an aldehyde occurs at lower frequencies than that of a ketone. In addition to the C=O absorption in an aldehyde, the aldehydic C–H bond also gives two peaks in the 2700–2800 cm-1 range. This absorption, coupled with the...
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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
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Spectroscopy of Carboxylic Acid Derivatives01:26

Spectroscopy of Carboxylic Acid Derivatives

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Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and...
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IR Spectroscopy: Molecular Vibration Overview01:24

IR Spectroscopy: Molecular Vibration Overview

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When Infrared (IR) radiation passes through a covalently bonded molecule, the bonds transition from lower to higher vibrational levels. The fundamental vibrational motions that result in infrared absorption can be classified as stretching or bending vibrations.
Stretching vibrations are vibrational motions that occur along the bond line, changing the bond length or distance between two bonded atoms. They are further distinguished as symmetric or asymmetric. In symmetric stretching, the...
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High-Resolution Rotational Spectroscopy of a Cyclic Ether.

F Gámez1, B Martínez-Haya1, S Blanco2

  • 1†Department of Physical, Chemical and Natural Systems, Universidad Pablo de Olavide, 41013 Seville, Spain.

The Journal of Physical Chemistry Letters
|August 20, 2015
PubMed
Summary
This summary is machine-generated.

Researchers studied the crown ether 1,4,7,10,13-pentaoxacyclopentadecane (15-crown-5) using microwave spectroscopy. Three stable conformations were identified, advancing supramolecular chemistry and host-guest interactions.

Keywords:
conformersinclusion complexesmacrocyclesmolecular recognitionmolecular structure

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Area of Science:

  • Supramolecular Chemistry
  • Physical Chemistry
  • Chemical Physics

Background:

  • Crown ethers are crucial in host-guest supramolecular chemistry.
  • Understanding crown ether conformations is vital for designing new molecules.
  • 1,4,7,10,13-pentaoxacyclopentadecane (15-crown-5) is a key cyclic ether.

Purpose of the Study:

  • To investigate the conformational landscape of 15-crown-5.
  • To identify and characterize stable rotamers of 15-crown-5.
  • To provide a foundation for studying related cyclic ethers.

Main Methods:

  • High-resolution rotational spectroscopy using molecular beam Fourier transform microwave spectroscopy.
  • Ab initio quantum chemical calculations at the MP2 level.
  • Analysis of rotational constants and centrifugal distortion coefficients.

Main Results:

  • Three stable rotamers of 15-crown-5 were successfully identified and characterized.
  • Experimental data were accurately reproduced by theoretical MP2 calculations.
  • Distinct structural features of the identified conformers were elucidated.

Conclusions:

  • The study successfully mapped key conformations of 15-crown-5.
  • This research provides a detailed understanding of the flexibility of cyclic ethers.
  • The findings pave the way for further conformational analysis of related compounds.