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Chemical Equilibrium in Supramolecular Systems as Studied by NMR Spectrometry

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Gloria Tardajos

Departamento de Química-Física, Facultad de Ciencias Químicas, Universidad Complutense, 28040, Madrid, Spain

Gustavo González-Gaitano

Departamento de Química y Edafología (sección de Química-Física), Universidad de Navarra, 31080, Pamplona, Spain

J. Chem. Educ., 2004, 81 (2), p 270

DOI: 10.1021/ed081p270

Publication Date (Web): February 1, 2004

Abstract

This experiment exposes undergraduate students to the field of supramolecular chemistry by means of an inclusion equilibrium between cyclic oligosaccharides (β- or γ-cyclodextrin) and surfactants (sodium octanoate or sodium decanoate) as studied by ¹H NMR. This technique is especially suitable in molecules that neither absorb nor emit optical radiation when excited. The induced chemical shifts that occur in both guest and host protons upon inclusion give valuable structural information about the stoichiometry and geometry of the complex, and permit the estimation of the binding constants through a nonlinear least-squares analysis of selected protons of the system. The effect of the host cavity size and hydrophobicity of the surfactant on the complex stability is also discussed.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Subject):

Equilibrium

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Citing Articles

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

Supramolecular Chemistry: Induced Circular Dichroism to Study Host−Guest Geometry
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Journal of Chemical Education2010 87 (9), 965-968
- Supramolecular Chemistry: Induced Circular Dichroism to Study Host−Guest Geometry
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  In this laboratory experiment, students obtain information about the structure of a host−guest complex from the interpretation of circular dichroism measurements. The value and sign of the induced circular dichroism (ICD) on an achiral chromophore guest ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Enhancement of the Chemiluminescence of Two Isoluminol Derivatives by Nanoencapsulation with Natural Cyclodextrins
Raquel Maeztu, Gustavo González-Gaitano and Gloria Tardajos
The Journal of Physical Chemistry B2010 114 (32), 10541-10549
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  The chemiluminescence (CL) yield of two isoluminol derivatives, N-(4-aminobutyl)-N-ethylisoluminol (ABEI) and N-(6-aminohexyl)-N-ethylisoluminol (AHEI), is remarkably increased in the presence of natural cyclodextrins (CDs). The most notable effect is ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Analysis of Citric Acid in Beverages: Use of an Indicator Displacement Assay
Alona P. Umali and Eric V. Anslyn, Aaron T. Wright, Clifford R. Blieden, Carolyne K. Smith, Tian Tian, Jennifer A. Truong, Caitlin E. Crumm, Jorge E. Garcia, Soal Lee, Meredith Mosier and Chester P. Nguyen
Journal of Chemical Education2010 87 (8), 832-835
- Analysis of Citric Acid in Beverages: Use of an Indicator Displacement Assay
  Alona P. Umali and Eric V. Anslyn, Aaron T. Wright, Clifford R. Blieden, Carolyne K. Smith, Tian Tian, Jennifer A. Truong, Caitlin E. Crumm, Jorge E. Garcia, Soal Lee, Meredith Mosier and Chester P. Nguyen
  Journal of Chemical Education2010 87 (8), 832-835
  The use of an indicator displacement assay permits the visualization of binding events between host and guest molecules. An undergraduate laboratory experiment is described to demonstrate the technique in the determination of citric acid content in ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Modern Developments in the Physical Chemistry Laboratory
Samuel A. Abrash
2007 973 (), 115-151
- Modern Developments in the Physical Chemistry Laboratory
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  Developments in the physical chemistry laboratory since the publication of the germinal text by Schwenz and Moore (1) are categorized and reviewed. The categories examined include modern instrumentation, current topics in chemistry, integrated ...
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Binary and Ternary Complexes Containing α-Cyclodextrin and Bromonaphthalene Derivatives: A Note of Caution in Interpreting UV Absorption Spectral Data
G. Barratt Park, David M. Brown, and Merlyn D. Schuh
The Journal of Physical Chemistry B2006 110 (45), 22510-22516
- Binary and Ternary Complexes Containing α-Cyclodextrin and Bromonaphthalene Derivatives: A Note of Caution in Interpreting UV Absorption Spectral Data
  G. Barratt Park, David M. Brown, and Merlyn D. Schuh
  The Journal of Physical Chemistry B2006 110 (45), 22510-22516
  Ultraviolet absorption spectra, NMR spectra, and phosphorescence measurements were used to confirm that α-cyclodextrin (CD) and 2-bromo-6-β-d-glucopyranosidylnaphthalene (BGN) form only a binary complex and to characterize its properties. The binding ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links