MU Chemistry 416 FS97

Articles of Chiroptical Methods
Optical Rotation, ORD and CD



Circular Dichroism - Principles and Applications Nakanishi, K.; Berova, N.; Woody, R. W.; Editors; VCH, New York, NY, 1994.
The best book on the market. Addresses all the modern applications of chiroptical methods. Includes a chapter on the octant rule as well. A rich source and a useful reference.

Circular Dichroism and Linear Dichroism. (Series: Oxford Chemistry Masters. Series editors: R. G. Compton, S. G. Davis and J. Evans.) A. Rodgers, B. Norden. Oxford University Press, Oxford, hardcover, 29.95 pounds, 1997. ISBN 0-19-855897-X
The book has been reviewed: Angew. Chem. Int. Ed. Engl. 1998, 37, 369-370.

Circular Polarization Spectroscopy of Chiral Molecules L. A. Nafie J. Mol. Struct. 1995, 347, 83-100.
An excellent description of circular polarized light and the measurement of ORD and CD. A must read. Note that I used this article extensively in my lecture.

The Chiroptical Properties of Carbonyl Compounds D. N. Kirk Tetrahedron 1986, 42, 777-818.
Dedicates all of section 3 to a discussion of the octant rule.

Optical Rotatory Dispersion and Circular Dichroism in Steroids Made It Possible, C. Djerassi, Profiles, Pathways, and Dreams Series, J. I. Seeman, Editor, American Chemical Society, Washington, D.C.
A historic account of early uses of ORD and CD in steroid chemistry.

ORD through the Eyes of Mathematica Novak, I. J. Chem. Educ. 1995, 72, 1084.
A nice read if you are into ORD. If you are a casual user, you might skip this one.

DNA-Binding Studies of Cu(bcp)2+ and Cu(dmp)2+: DNA Elongation without Intercalation of Cu(bcp)2+. McMillin, D. R. J. Am. Chem. Soc. 1993, 115, 6699-6704.
(Summary Sheet)

Right-Handed Triplex Formed between Peptide Nucleic Acid PNA-T8 and Poly(dA) Shown by Linear and Circular Dichroism Spectroscopy. Nielsen, P. E. et al. J. Am. Chem. Soc. 1993, 115, 6477-6481.
(Summary Sheet)

Chiral Curiosities Voegtle et al. J. Am. Chem. Soc. 1997, 119, 10547-xxxx.
This article was highlighted in C&EN's Science & Technology Concentrates as follows: Certain curious molecules can be chiral even though they are made up of constitutents that are achiral. A team of chemists in Japan and Germany has separated examples of several such compounds into enantiomers and finds the pure enatiomers have pronounced circular dichroism. For instance, Yoshio Okamoto and coworkers at Nagoya University in Nagoya, Japan, and Fritz Voegtle of Bonn, Germany, find that a "rotaxane" can be separated into enantiomers. The rotaxane, which consists of an unsymmetrical "dumbbell" threaded through a "wheel", exhibits "cycloenantiomerism". In one enantiomer, the sequence of functional groups arrayed around the wheel has a clockwise orientation circling the dumbbell and vice versa. The researchers similarly have separated enantiomers of a topologically chiral catenane (interlocking rings) and a pretzel shaped molecule in which an intramolecular bridge links the two rings of a catenane.

The Chiral N-S Axis ion Sulfenamides. Mearv Ben-David Blanca, Eric Maimon, and Daniel Kost Angew. Chem. Int. Ed. Engl. 1997, 36, 2216-2219.
The first successful separation of enantiomers due to hindered rotation about a sulfenamine N-S bond is reported. The enantiomers were characterized via CD spectroscopy. (Contains interesting inversion recovery NMR as well.)