MU Chemistry 416 FS97

Literature List on Spin-Spin Coupling


Test for Chemical Shift and Magnetic Equivalence in NMR A. Ault J. Chem. Educ. 1974, 11, 729-731.
There are problems with this article. I think this article confuses more than it helps. Read it and see what I mean.

Chemical Shift Equivalence and Magnetic Equivalence in Conformationally Mobile Molecules R. M. Silverstein, R. T. LaLonde J. Chem. Educ. 1980, 57, 343-344.
This article is excellent. Everything that is being said is correct and the paper is structured very well. A must-read for all of you.

Useful Examples for Discussion of Proton-NMR Spectroscopy: N-Substituted alphja-Aminobenzenebutanenitriles - Anisotropy of Diastereotopic Methylene Protons. J. Almy, R. M. Alvarez, A. H. Fernandez, A. S. Vazquez J. Chem. Educ. 1997, 74, 1479-1482.
The title compounds contains two methylene groups in the beta and gamma positions od a chiral (at alpha-C) aminonitrile. Which one of the methylene groups shows the larger chemical shift difference for the two diasterotopic H-atoms? Guess again! Take a good look at the solvent dependency of the gamma protons (Figure 1). Unless you know that the spectra of clean compounds can look this messy, you just might think that your compounds aren't really clean ...

A Practical Guide to First-Order Multiplet Analysis in 1H-NMR Spectroscopy. Thomas R. Hoye, Paul R. Hanson, and James R. Vyvyan J. Org. Chem. 1994, 59, 4096-4103.
This paper presents a systematic approach for deducing the complete set of coupling constants from complex multiplets (so long as first order rules are valid).

Using High-Field NMR to Determine Dehydrogenase Stereospecificity with Respect to NADH - An Undergraduate Biochemistry Lab S, B. Mostad, A. Glasfeld J. Chem. Educ. 1993, 70, 504-506.
An excellent demonstration of the NMR spectrum of a methylene group with enantiotopic H-atoms in a chiral environment. Also demonstrates the Karplus correlation at work. Make sure to understand fully the spectra shown in Figure 3.

A First-Order Coupled Nuclei NMR Spectrum: 2-Bromo-4-Fluoroanisole J. P. Canselier J. Chem. Educ. 1973, 50, 291.
This article demonstrates a very nice example of an AKMX spin system. The AKM part are three aromatic H-atoms and the X is a fluorine.

Solving Molecular Structures Using NMR and Molecular Mechanics - An Undergraduate Research Project E. L. Anderson, D. Li, N. L. Owen J. Chem. Educ. 1992, 69, 846-849.
This article demonstrates a very nice example of an ABMX spin system. The ABM system are three H-atoms in benzene and the X is 31P. The paper contains both the experimental spectrum and a successful simulation of that spectrum. Make sure to understand Figure 2 in this paper.

False AA'X Spin-Spin Coupling Systems in 13C-NMR: Examples Involving Phosphorus and a 20-Year-Old Mystery in Off-Resonance Decoupling. W. H. Hersh J. Chem. Educ. 1997, 74, 1485-1489.
Read the first half of this article. Recognize the ABX systems in Figure 2 and take a look at the many divers types of multiplets (in Figure 3) you can get depending on the various couplings.

The Nature of the Metal-Silicon Bond in [M(SiR3H3(PPh3)3] (M = Ru, Os) and the Crystal Structure of [Os{Si(N-pyrrolyl)3H3(PPh3)]. K. Huebler, U. Huebler, W. R. Roper, P. Schwerdtfeger, L. J. Wright Chem. Eur. J. 1997, 3, 1608-1616.
This paper demonstrates an interesting example of an AA'A"XX'X" spin system. The A atoms are hydride H atoms and the X atoms are phosphane P atoms. The kind of second-order spectrum one can only "understand" via a simulation.

Carbon-Carbon and Carbon-Nitrogen Spin-Spin Coupling in NMR Spectrsocopy. - Simple Examples Based on Isotope-Labeled Glycines. L. Grehn, U. Ragnarsson, C. J. Welch J. Chem. Educ. 1997, 74, 1477-1479.
Several 100.4 MHz 13C- and a 40.4 MHz 15N-NMR spectra are given for isotopically labeled Boc-glycines and related materials. Take a look. The spectrum in Figure 3 is particularly interesting and there clearly is a mistake in that the isomers cannot be of the E/Z type. What are these isomers instead?
(Supplemental material available)