Moss, Robert A.

Position:

L. P. Hammett Professor

	Phone:	732-445-2606
	E-mail:
	FAX:	732-445-5312
	Lab:	732-445-2632
	Office:	Wright Rieman Labs 386/392
	Mail:	Chemistry & Chemical Biology, 610 Taylor Road, Piscataway, NJ 08854

Education	Links
B.S. 1960, Brooklyn College M.S. 1962, University of Chicago Ph.D. 1963, University of Chicago NAS-NRC Postdoctoral Fellow, Columbia University, 1963-64 A.P. Sloan Foundation Fellow, 1971-73 National Institutes of Health Special Postdoctoral Fellow, 1971-72 Visiting Scientist at MIT, 1971-72 Academic Visitor at the University of Oxford, 1976-77 Erna and Jakob Michael Visiting Professor, Weizmann Institute, Israel, 1984 Distinguished Visiting Scientist, National Research Council of Canada, 1988 Wynberg Visiting Professor, University of Groningen, Netherlands, 1992 Forchheimer Visiting Professor, Hebrew University, Jerusalem, Israel, 1999	See news story: "Robert Moss wins a 2010 Arthur C. Cope Scholar Award of the American Chemical Society"

Education

Links

B.S. 1960, Brooklyn College
M.S. 1962, University of Chicago
Ph.D. 1963, University of Chicago
NAS-NRC Postdoctoral Fellow, Columbia University, 1963-64
A.P. Sloan Foundation Fellow, 1971-73
National Institutes of Health Special Postdoctoral Fellow, 1971-72
Visiting Scientist at MIT, 1971-72
Academic Visitor at the University of Oxford, 1976-77
Erna and Jakob Michael Visiting Professor, Weizmann Institute, Israel, 1984
Distinguished Visiting Scientist, National Research Council of Canada, 1988
Wynberg Visiting Professor, University of Groningen, Netherlands, 1992
Forchheimer Visiting Professor, Hebrew University, Jerusalem, Israel, 1999

See news story: "Robert Moss wins a 2010 Arthur C. Cope Scholar Award of the American Chemical Society"

Research Summary

Research in my laboratory concerns physical organic chemistry; specifically the chemistry of reactive intermediates.

The Chemistry of Reactive Intermediates

Research in my laboratory focuses on organic reaction mechanisms, specifically the chemistry of short-lived reactive intermediates, such as carbenes, carbocations, radicals, and ion pairs. We use fast spectroscopic and kinetic techniques to probe these reactions and to measure the lifetimes of the transient species. Nanosecond and picosecond laser flash photolysis are the key methodologies. Ongoing collaborations with other laboratories also permit us to use advanced computational methods, matrix isolation spectroscopy, time resolved infrared spectroscopy, and ultrafast kinetic methods to study reactive intermediates. We are thus able to follow the evolution of the transient intermediates at very short reaction times. We also develop new synthetic methods to construct precursors (mainly diazirines) for the generation of novel reactive intermediates.

Our research is supported by the National Science Foundation and the Petroleum Research Fund.

conversion of isopropoxychlorodiazirine to isopropoxychlorocarbene

Reaction Profile for conversion of isopropoxychlorodiazirine to isopropoxychlorocarbene with AlCl₃

Awards & Honors

2010 Arthur C. Cope Scholar Award of the American Chemical Society
Chair, Coordinating Committee, International Symposia on Reactive Intermediates and Unusual Molecules, 2008-2010
Sr. Marian Jose Smith Excellence in Education Award, North Jersey Section, American Chemical Society, 2002
Editorial Advisory Board, Langmuir, 2000-2002
Section Committee, Section on Chemistry, AAAS, 1995-1999
Fellow, AAAS, 1992
Editorial Advisory Board, Journal of Organic Chemistry, 1979-1984

Publications

"Ultrafast Spectroscopy of Arylchlorodiazirines: Hammett Correlations of Excited State Lifetimes," Y. Zhang, L. Wang, R.A. Moss, and M.S. Platz, J. Am. Chem. Soc., 131, 16652 (2009).

"Innermolecular Reactions of Fluorophenylcarbene Inside a Hemicarcerand," Z. Lu, R.A. Moss, R.R. Sauers, and R. Warmuth, Organic Lett. 11, 3866 (2009).

"Latent Nucleophilicity of Dichlorocarbene," R.A. Moss, M. Zhang, and K. Krogh-Jespersen, Organic Lett., 11, 1947 (2009).

"A New Synthesis of Difluorodiazirine and the Absolute Reactivity of Difluorocarbene," R.A. Moss, L. Wang, and K. Krogh-Jespersen, J. Am. Chem. Soc., 131, 2128 (2009).

"Ionic and Radical Fragmentations of Alkoxyhalocarbenes - A Perspective," R.A. Moss, J. Phys. Org. Chem., 22, 265 (2009).

"Activation Parameters for Additions of Ambiphilic Methoxychlorocarbene to Alkenes," R.A. Moss and Min Zhang, Organic Lett., 10, 4045 (2008).

"Enthalpy versus Entropy in Chlorocarbene/Alkene Addition Reactions," R.A. Moss, L. Wang, M. Zhang, C. Skalit, and K. Krogh-Jespersen, J. Am. Chem. Soc., 130, 5634 (2008).

The Solvation of Carbenes: π and Ylidic Complexes of p-Nitrophenylchlorocarbene," R.A. Moss, L. Wang, E. Weintraub, and K. Krogh-Jespersen, J. Phys. Chem. A, 112, 4651 (2008).

"Chlorofluorocarbene: First UV Observation of a Dihalocarbene in Solution," R.A. Moss, J. Tian, R.R. Sauers, C. Skalit, and K. Krogh-Jespersen, Organic Lett., 9, 4053 (2007).

"Tracking "Invisible" Alkylchlorocarbenes by Their Sigma to Pi Absorptions: Dynamics and Solvent Interactions," R.A. Moss, J. Tian, R.R. Sauers, and K. Krogh-Jespersen, J. Am. Chem. Soc., 129, 10019 (2007).

"New Mechanisms Centered on Reactive Intermediates: Examples from Diazirine and Carbene Chemistry," R.A. Moss, J. Tian, G. Chu, R.R. Sauers, and K. Krogh-Jespersen, Pure Appl. Chem., 79, 993 (2007).

"S_Ni Fragmentations of Alkoxychlorocarbenes - A Perspective," R.A. Moss, X. Fu, and R.R. Sauers, J. Phys. Org. Chem., 20, 1 (2007).

Reviews in Reactive Intermediate Chemistry, M.S. Platz, R.A. Moss, and M. Jones, Jr., Editors, Wiley, New York, 2007.

"The Synthesis of Dichlorodiazirine and the Generation of Dichlorocarbene: Spectroscopy and Structure of Dichlorocarbene-Ylides," R.A. Moss, J. Tian, R.R. Sauers, D.H. Ess, K.N. Houk, and K. Krogh-Jespersen, J. Am. Chem. Soc, 129, 5167 (2007).

"Comparative Stereochemistry of the Fragmentation of Oxychlorocarbenes, Chlorocarbonates, and Chlorosulfites in the 3-Nortricyclyl/5-Norbornen-2-yl System," R.A. Moss and X. Fu, Tetrahedron Lett., 47, 357 (2006).

"Diazirines: Carbene Precursors Par Excellence," R.A. Moss, Acc. Chem. Res., 39, 267 (2006).

"Hammett Studies of Aryldichloromethide Carbanion Reactions," R.A. Moss and J. Tian, Organic Lett., 8, 1245 (2006).

"Modulation of Selectivity in a Fluorocarbene Cyclopropanation Reaction: A Catalytic Role for Bromide Ion," R.A. Moss and J. Tian, Tetrahedron. Lett, 47, 3419 (2006).

"The Fragmentation of 2,2,2-Triphenylethoxychlorocarbene: Evidence for Ultrafast Fragmentation-Rearrangement in Excited Diazirines," X. Fu, R.A. Moss, P. Piotrowiak, M. Myahkostupov, and I.R. Gould, Organic Lett., 8, 4807 (2006).

"Conformational Product Control in the Low-Temperature Photochemistry of Cyclopropylcarbenes," P.S. Zuev, R.S. Sheridan, R.R. Sauers, R.A. Moss, and G. Chu, Organic Lett., 8, 4963 (2006).

"Ultrafast Spectroscopic Study of the Photochemistry and Photophysics of Arylhalodiazirines; Direct Observation of Carbene and Zwitterion Formation," J. Wang, G. Burdzinski, J. Kubicki, M.S. Platz, R.A. Moss, X. Fu, P. Piotrowiak, and M. Myahkostupov, J. Am. Chem. Soc., 128, 16446 (2006).

Research Areas:

Organic Chemistry