Band-Selective 2D HSQMBC: A Universal Technique for Detection and Measurement of 35,37Cl Isotope Effects for 13C Nuclei

Josep Saurí; Mikhail Reibarkh; Ting Zhang; Ryan D Cohen; Xiao Wang; Tadeusz F Molinski; Gary E Martin; R Thomas Williamson

doi:10.1021/acs.orglett.6b02158

Band-Selective 2D HSQMBC: A Universal Technique for Detection and Measurement of ^35,37Cl Isotope Effects for ¹³C Nuclei

Org Lett. 2016 Oct 7;18(19):4786-4789. doi: 10.1021/acs.orglett.6b02158. Epub 2016 Sep 28.

Authors

Josep Saurí^{1

2}, Mikhail Reibarkh^{1

2}, Ting Zhang^{1

2}, Ryan D Cohen^{1

2}, Xiao Wang^{1

2}, Tadeusz F Molinski^{1

2}, Gary E Martin^{1

2}, R Thomas Williamson^{1

2}

Affiliations

¹ NMR Structure Elucidation, Process Research and Development and ‡Discovery Chemistry, MRL, Merck & Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
² Department of Chemistry and Biochemistry and ∥Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego , 9500 Gilman Drive MC-0358, La Jolla, California 92093, United States.

PMID: 27681329
DOI: 10.1021/acs.orglett.6b02158

Abstract

A novel technique that allows efficient measurement of the ^35,37Cl isotope pattern for any ¹³C resonance has been developed. The band-selective CLIP-HSQMBC experiment is reliable and universally applicable for the indirect measurement of the ^35,37Cl isotope shift of ¹³C resonances. The experiment provides advantages over conventional 1D ¹³C NMR and the recently developed bs-HSQC experiments. The utility and performance of the bs-CLIP-HSQMBC experiment is demonstrated for polyhalogenated synthons in a synthetic route and for a polyhalogenated marine natural product.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Biological Products / chemical synthesis
Biological Products / chemistry
Carbon Isotopes
Chlorine / analysis*
Hydrocarbons, Halogenated / chemical synthesis
Hydrocarbons, Halogenated / chemistry
Isotopes / analysis*
Magnetic Resonance Spectroscopy / methods*
Molecular Structure
Protons

Substances

Biological Products
Carbon Isotopes
Chlorine-37
Hydrocarbons, Halogenated
Isotopes
Protons
Chlorine
Carbon-13