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Enantiomeric Excess Determination by Fourier Transform Near-Infrared Vibrational Circular Dichroism Spectroscopy: Simulation of Real-Time Process Monitoring

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Abstract:

The first use of near-infrared (NIR) Fourier transform vibrational circular dichroism (FT-VCD) to follow changes in the enantiomeric excess (EE) of chiral sample molecules in time using a flow-cell sampling apparatus is reported. Simultaneous changes in the fractional composition and the EE of a mixture of two different chiral molecules were monitored as a function of time. This simulates the progress of the chemical reaction from a chiral reactant to a chiral product where the mole fractions and EE values of both species may change with time. For the molecules studied, α-pinene, camphor, and borneol, the accuracy of following EE changes for one species alone is approximately 2%, while for simultaneously following EE changes in two species it is approximately 3% for 30 min sampling periods at 16 cm−1 spectral resolution. These findings demonstrate the potential for VCD to be used in the NIR region for real-time monitoring of the composition and %EE of chemical reactions involving the synthesis of chiral molecules.

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/0003702055012573

Affiliations: 1: Department of Chemistry, Syracuse University, Syracuse, New York 13244 (C.G., X.C., T.B.F., L.A.N.); Johnson & Johnson Pharmaceutical Research & Development, LLC, Spring House, Pennsylvania 19477 (R.D.S.); and BioTools, Inc., 950 N. Rand Road, Unit 123, Wauconda, Illinois 60084 (R.K.D., L.A.N.) 2: Department of Chemistry, Syracuse University, Syracuse, New York 13244 (C.G., X.C., T.B.F., L.A.N.); Johnson & Johnson Pharmaceutical Research & Development, LLC, Spring House, Pennsylvania 19477 (R.D.S.); and BioTools, Inc., 950 N. Rand Road, Unit 123, Wauconda, Illinois 60084 (R.K.D., L.A.N.) 3: Department of Chemistry, Syracuse University, Syracuse, New York 13244 (C.G., X.C., T.B.F., L.A.N.); Johnson & Johnson Pharmaceutical Research & Development, LLC, Spring House, Pennsylvania 19477 (R.D.S.); and BioTools, Inc., 950 N. Rand Road, Unit 123, Wauconda, Illinois 60084 (R.K.D., L.A.N.)

Publication date: September 1, 2005

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