Container Molecules and Their Guests

by Donald J. Cram

This volume covers the evolution of host-guest complexation chemistry in the minds and hands of Nobel Prize winner Donald Cram and his co-workers at UCLA, over the 25-year period from 1970-1994. It deals with the fundamental principles and objectives that govern this rapidly developing subject and illustrates the emergence of a new field of biomimetic chemistry.
The book demonstrates how a number of techniques, such as molecular modeling, synthesis, crystal structure, NMR solution structure and mass spectral structure determinations can be combined to develop a new branch of organic chemistry. It discusses the chemistry of completely new families of complexes - the carceplexes, hemicarceplexes and velcarplexes - and reviews for the first time the uses of the interiors of hemicarceplexes as a new phase for carrying out chemical reactions and for protecting unstable species.
Container Molecules and Their Guests illustrates how complexation and decomplexation rates are measured to provide free energies of binding, discusses new phenomena such as constrictive binding, and shows for the first time how solvophobic forces drive complexation in a variety of organic solvents, giving examples of entropy-driven complexations. It also covers catalysis through complexation and chiral recognition in catalysis, both secondary themes of this volume, and points to questions that it would not previously have been possible to ask, examining how such questions might be answered through research.
Container Molecules and Their Guests will provide stimulating reading for researchers, post-graduate students and teachers involved in bio-organic chemistry, organic chemistry, materials science, and medicinal and pharmaceutical chemistry. Many will be inspired by the wonderful achievements that Cram and his team have made in this exciting branch of supramolecular chemistry.

238 pages, Hardcover

First published December 1, 1994

About the author

Donald James Cram (April 22, 1919 – June 17, 2001) was an American chemist who shared the 1987 Nobel Prize in Chemistry with Jean-Marie Lehn and Charles J. Pedersen "for their development and use of molecules with structure-specific interactions of high selectivity." They were the founders of the field of host-guest chemistry.

Cram was born and raised in Chester, Vermont, to a Scottish immigrant father, and a German immigrant mother. His father died before Cram turned four, leaving him the only male in a family of five. He grew up on Aid to Dependent Children, and learned to work at an early age, doing jobs such as picking fruit, tossing newspapers, and painting houses, while bartering for piano lessons.

Cram attended the Winwood High School in Long Island, N.Y. From 1938 to 1941, he attended Rollins College, in Winter Park, Florida on a national honorary scholarship. It was at Rollins that he became known for building his own chemistry equipment. In 1941, he graduated from Rollins College with a B.S. in Chemistry.

In 1942, he graduated from the University of Nebraska–Lincoln with a M.S. in Organic Chemistry, with Norman O. Cromwell serving as his thesis adviser. He subject was "Amino ketones, mechanism studies of the reactions of heterocyclic secondary amines with -bromo-, -unsaturated ketones."

In 1947, Cram graduated from Harvard University with a Ph.D. in Organic Chemistry, with Louis Fieser, serving as the adviser on his dissertation on "Syntheses and reactions of 2-(ketoalkyl)-3-hydroxy-1,4-naphthoquinones"

From 1942-1945, Cram worked in chemical research at Merck & Co laboratories, doing penicillin research with mentor Max Tishler. Postdoctoral work was as an American Chemical Society postdoctoral fellow at the Massachusetts Institute of Technology, with John D. Roberts. Cram was the originator of Cram's rule, which provides a model for predicting the outcome of nucleophilic attack of carbonyl compounds. He published over 350 research papers and eight books on organic chemistry, and taught graduate and post-doctoral students from 21 different countries.

Cram expanded upon Charles Pedersen's ground-breaking synthesis of crown ethers, two-dimensional organic compounds that are able to recognize and selectively combine with the ions of certain metal elements. He synthesized molecules that took this chemistry into three dimensions, creating an array of differently shaped molecules that could interact selectively with other chemicals because of their complementary three-dimensional structures. Cram's work represented a large step toward the synthesis of functional laboratory-made mimics of enzymes and other natural molecules whose special chemical behavior is due to their characteristic structure. He also did work in stereochemistry and Cram's rule of asymmetric induction is named after him.

Cram was named an assistant professor at the University of California, Los Angeles in 1947, and a professor in 1955. He served there until his retirement in 1987. He was a popular teacher, having instructed some 8,000 undergraduates in his career and guided the academic output of 200 graduate students. He entertained his classes by strumming his guitar and singing folk songs.