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Journal article
Cyclohexanecarbonitriles: Assigning Configurations at Quaternary Centers from C-13 NMR CN Chemical Shifts
Journal of organic chemistry, v 74(9), pp 3551-3553
01 May 2009
PMID: 19348434
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
C-13 NMR chemical shifts of the nitrile carbon in cyclohexanecarbonitriles directly correlate with the configuration of the quaternary, nitrile-bearing stereocenter. Comparing C-13 NMR chemical shifts for over 200 cyclohexanecarbonitriles reveals that equatorially oriented nitrites resonate 3.3 ppm downfield, on average, from their axial counterparts. Pairs of axial/equatorial diastereomers varying only at the nitrile-bearing carbon consistently exhibit downfield shifts of delta 0.4-7.2 for the equatorial nitrile carbon, even in angularly substituted decalins and hydrindanes.
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Details
- Title
- Cyclohexanecarbonitriles: Assigning Configurations at Quaternary Centers from C-13 NMR CN Chemical Shifts
- Creators
- Fraser F. Fleming - Duquesne UniversityGuoqing Wei - Duquesne University
- Publication Details
- Journal of organic chemistry, v 74(9), pp 3551-3553
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 3
- Grant note
- R15AI051352 / NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of Allergy & Infectious Diseases (NIAID) 2R15AI051352 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA CHE 0808996 / NSF; National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000265554900046
- Scopus ID
- 2-s2.0-66449126273
- Other Identifier
- 991020898394804721
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- Web of Science research areas
- Chemistry, Organic