Classic Carbenes and Carbene Complexes
Thursday, March 22nd, 2012
12:45 PM Room 1093 Shelby Hall
A Chemist’s Avocation: A Celebration of Sir Arthur Conan Doyle and Sherlock Holmes
Friday, March 23rd, 2012
3:30 PM Room 1093 Shelby Hall
(General Audience Lecture)
Professor Robert A. Moss is Research Professor and Louis P. Hammett Professor Emeritus at Rutgers, the State University of New Jersey, New Brunswick, NJ. Robert was born in Brooklyn, NY in May 1940. He obtained his B.S. degree from Brooklyn College in 1960 then moved to the University of Chicago to conduct graduate research under the direction of Professor Gerhard Closs. After earning his PhD in 1963, Robert served as an NAC-NRC Postdoctoral Fellow with Professor Ronald Breslow at Columbia. Robert started his independent research career at Rutgers in 1964 and has remained there since. Professor Moss has spent time as a Visiting Scientist or Visiting Professor at several leading research institutions including MIT (1971-72); Oxford (1976-77); the Weizmann Institute, Israel (1984); the National Research Council of Canada (1988); the University of Groningen, Netherlands (1992); and Hebrew University, Jerusalem (1999).
Robert is universally recognized as a leader in the field of carbene chemistry, although his mechanistic investigations also involve other transient species including carbocations and radicals. Professor Moss’ studies encompass devising new carbene precursors; using laser flash photolysis, matrix isolation spectroscopy, ultrafast kinetic methods, and time resolved IR spectroscopy to determine activation parameters, reaction kinetics, and lifetimes of transient species; and application of advanced computational methods to predict kinetic and thermodynamic parameters of fast reaction entities.
Professor Moss expanded the synthesis and use of diazirines as direct precursors to unstable carbenes through thermal or photochemical activation. He has generated and studied many elusive carbenes including dimethoxycarbene, difluorocarbene, mixed dihalocarbenes, and various ephemeral organohalocarbenes, to name a few. Robert was the first to experimentally evaluate the electrophilicity of singlet carbenes using a kinetic model. Based upon this work, he devised a novel scale of carbenic philicity as a tool to help predict and classify the relative electrophilicities, ambiphilicities, or nucleophilicities of substituted carbenes. The Moss carbenic philicity scale quickly became an indispensible resource for researchers involved in multiple fields of physical organic chemistry. Robert also disclosed an efficient azide and fluoride exchange reaction of halodiazirines and the first general procedure for the preparation of unsymmetrical azoxyalkanes. In 2005, Robert generated fluorophenoxycarbene inside a hemicarcerand. This was the first electron-deficient singlet carbene ever stabilized by trapping.
Professor Moss’ investigations of transient intermediates have greatly enhanced our knowledge of the mechanistic pathways, energies, and lifetimes of such species. However, Robert has contributed to other areas of chemistry aside from the generation and study of reactive intermediates. Professor Moss, with support from the U.S. Army Research Office, developed micelles capable of encapsulating and destroying organophosphate nerve agents. He devised other surfactant systems for remediating phosphate pollutants from the environment. Robert also creatively used supramolecular aggregates to promote peptide-catalyzed enantioselective hydrolysis of amino acid esters and to effect phosphodiester and ester cleavage by surfactant-complexed lanthanides or iodoso- and iodoxybenzoates.
Professor Moss was an NIH Special Postdoctoral Fellow (1971-72) and an A. P. Sloan Fellow (1971-73) early in his career. Later, Professor Moss was named a Fellow of both the American Association for the Advancement of Science (1992) and the American Chemical Society (2011). He was also recognized for his important contributions to chemistry through a National Science Foundation Special Creativity Award (2007-2008) and an A. C. Cope Scholar Award (2010). Robert was a member of the Editorial Advisory Board of Journal of Organic Chemistry from 1979-1984 and ofLangmuir from 2000-2002. He remains the Chair of the Coordinating Committee for International Symposia on Reactive Intermediates and Unusual Molecules, a position he has held since 2008. Enviably, Professor Moss has maintained continuous financial support from the National Science Foundation since 1965. He has trained nearly 130 graduate students and postdoctoral associates in his 47 years at Rutgers. To date, Robert and his students have authored over 420 journal and review articles, most related to their seminal investigations of various unstable carbenes or chemically reactive surfactants. He is also a co-editor of, and contributing author to, the popular Wiley book, “Reactive Intermediate Chemistry.” When not solving the mysteries behind the generation, lifetimes, and reactivities of transient species, Robert enjoys analyzing the adventures of literature’s most renowned chemist, Detective Sherlock Holmes.