OPEN ACCESS

STUDIES OF RATES OF CONVERSION AND POPULATIONS OF VARIOUS CONFORMATIONS OF SATURATED RING COMPOUNDS BY N.M.R.: I. CHLOROCYCLOHEXANE AND BROMOCYCLOHEXANE

Publication: Canadian Journal of Chemistry
August 1960

Abstract

The populations of equatorial and axial halogen forms of chloro- and bromo-cyclohexane have been studied by proton magnetic resonance between 25° and −104 °C in carbon disulphide solution. From the equilibrium constants obtained the free energy change between the two conformations is obtained. The bromo compound has 82% of the equatorial halogen form and the chloro compound 77%. Estimates of the populations are also available for room temperature from the chemical shift measurements. The energy barrier for conversion between the two forms is approximately 10,850 calories. A simple Lennard-Jones potential with the available estimates of van der Waals radii is used to calculate the differences in energy of the two forms.

Résumé

non disponible

Formats available

You can view this article in more than one different formats.

Information & Authors

Information

Published In

cover image Canadian Journal of Chemistry
Canadian Journal of Chemistry
Volume 38Number 8August 1960
Pages: 1241 - 1248

History

Published online: 3 February 2011

Permissions

Request permissions for this article.

Authors

Affiliations

Metrics & Citations

Metrics

Other Metrics

Citations

Cite As

Export Citations

If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. Simply select your manager software from the list below and click Download.

Cited by

1. Dispersion and Halogen-Bonding Interactions: Binding of the Axial Conformers of Monohalo- and (±)- trans -1,2-Dihalocyclohexanes in Enantiopure Alleno-Acetylenic Cages
2. Table of Conformational Energies-1967
3. The Study of Intramolecular Rate Processes by Dynamic Nuclear Magnetic Resonance
4. An FT-Raman Spectroscopic Study of the Conformational Properties of Chlorocyclohexane in Zeolites
5. Vibrational dephasing in bromocyclohexane: how to separate contributions from different mechanisms
6. A Raman study of solvent effects on vibrational dynamics of axial and equatorial conformers in chlorocyclohexane
7. Electron transfer reactions and associated conformational changes
8. Dynamique Moléculaire des Chloro-4 et Bromo-4 Méthylènecyclohexanes par Résonance Magnétique Nucléaire du13C
9. Concentration dependence of free enthalpies of activaton of conformational transitions of some alkyl chlorides in nujol
10. Composes heterocycliques spiranniques—V
11. Stereochemische Untersuchungen mit der 13C-NMR-Spektroskopie; Die Bestimmung des Konformationsgleichgewichtes am 1r, 2c,3t, 4t-Tetramethylcyclohexan mit Hilfe der 13C-NMR-Spektroskopie
12. Zusammenhänge zwischen dem epimerenverhältnis bei der hydrogen[35s]sulfitaddition an hex-5-enopyranoside und nicht-bindenden wechselwirkungsenergien am pyranosering
13. Conformational Processes in Rings
14. Ultrasonic velocity dispersion in methylcyclohexane
15. Conformational analysis—CI
16. Origine de la différence de déplacements chimiques des protons en α du carbonyle dans les cyclohexanones
17. NMR conformational analysis of saccharides and polysaccharides
18. Determination of the activation energy of chlorocyclohexane conformational transitions by infrared spectra
19. Structural and Stereochemical Applications
20. The Investigation of the Kinetics of Conformational Changes by Nuclear Magnetic Resonance Spectroscopy
21. Conformational studies on pyranoid sugar derivatives by NMR spectroscopy. Correlations of observed proton—proton coupling constants with the generalized Karplus equation
22. Conformational Analysis of Sugars and Their Derivatives
23. Conformational studies on pyranoid sugar derivatives.
24. REFERENCES
25. REFERENCES
26. Chapter 3 Applications of 1H nuclear magnetic resonance spectroscopy to the conformational analysis of cyclic compounds
27. Chapter 2 Experimental Methods for the Study of Fast Reactions
28. Etude de l'equilibre conformationnel du bromocyclohexane-D4.
29. NMR-untersuchung zur konformation von derivaten des 1,4-dioxens
30. Self-Diffusion in Some Plastic Crystals
31. Analyse conformationnelle par resonance nucleaire magnetique—III
32. CORRELATIONS OF 1H RESONANCE SPECTRAL PARAMETERS WITH MOLECULAR STRUCTURE
33. Chapter 10 Correlations of 1H resonance spectral parameters with molecular structure
34. 2,6-Dialkylpiperazines. III. NMR spectra of the geometrical isomers of 4-phenyl-2,6-dimethylpiperazine
35. Kernresonanzspektroskopische Konformationsanalyse an Cyclohexanderivaten
36. Konformationsanalyse beweglicher Cyclohexan-Systeme
37. Ultrasonic Relaxation and Axial—Equatorial Isomerization in Methylcyclohexane. II
38. Verbindungen mit drei Ringen über einer C—C-Bindung, I. Tricyclo[4.4.3.0]tridecanon-(11), Tricyclo[4.4.4.0]tetradecanon-(2) und -dion-(2.3)
39. Konstellationsanalyse mit Hilfe der Kernresonanzspektroskopie, I Konstellationsanalyse an substituierten Cyclohexanen
40. Analyse conformationnelle par résonance nucléaire magnétique II. Différence d'enthalpie et d'enthalpie libre entre conformères des chloro-et bromocyclohexanes
41. Chapter 9 The effects of chemical equilibria and molecular conformational motion on NMR spectra
42. N.M.R. Measurements of Reaction Velocities and Equilibrium Constants as a Function of Temperature
43. Hydrogenation of 1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone with a copper chromite catalyst
44. Die multiple Isomerisierung von Brom-decahydroisochinolinen. Decahydroisochinoline. I. Teil
45. Spezielle Anwendungsgebiete
46. NMR Study of Rotational Barriers and Conformational Preferences. I. Cyclohexyl Fluoride
47. Nuclear magnetic resonance spectra of the γ and δ isomers of 1,2,3,4,5,6-hexachlorocyclohexane
48. The Study of Chemical Rate Processes in Liquids by Nuclear Magnetic Resonance
49. NMR Spectra of Some Cyclohexyl Derivatives
50. NUCLEAR MAGNETIC RESONANCE SPECTRA OF SIX-MEMBERED ALCYCLIC RING COMPOUNDS AT LOW TEMPERATURE: IV. PARTIALLY DEUTERATED 1,2-trans-CHLOROIODOCYCLOHEXANE
51. Conformational equilibria by nuclear magnetic resonance spectroscopy
52. Long‐Range Nuclear Magnetic Shielding in Molecules and the Anisotropy in the Magnetic Susceptibility of a Carbon‐Carbon Single Bond
53. Studies of Rates of Conversion and Populations of Conformations in Saturated Ring Compounds. III. NN ′ Dimethyl Piperazine

View Options

View options

PDF

Download PDF

Get Access

Login options

Check if you access through your login credentials or your institution to get full access on this article.

Subscribe

Click on the button below to subscribe to Canadian Journal of Chemistry

Purchase options

Purchase this article to get full access to it.

Restore your content access

Enter your email address to restore your content access:

Note: This functionality works only for purchases done as a guest. If you already have an account, log in to access the content to which you are entitled.

Media

Media

Other

Tables

Share Options

Share

Share the article link

Share with email

Share on social media