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15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers.
Magn Reson Chem. 2010 Nov; 48(11):873-6.MR

Abstract

In this article, we describe the characteristic (15)N chemical shifts of isatin oxime ethers and their isomer nitrone. These oxime ethers and nitrones are the alkylation reaction products of isatin oximes. In our study, the (15)N chemical shifts observed in these oxime ethers were in the 402-408 (or 22-28) ppm range, although those for their corresponding nitrone series were in the 280-320 (or -100 to -60) ppm range. This remarkable difference in (15)N NMR chemical shift values could potentially be used to determine the O- versus N-alkylation of oximes, even when only one isomer is available. In this paper, the differences in (15)N NMR chemical shifts serve as the basis for a discussion about how to distinguish both regioisomers derived from the oximes alkylation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu X
Department of Drug Metabolism, Covance Company, 3301 Kinsman Boulevard, Madison, WI 53704, USA.
Huang XS
No affiliation info available
Sin N
No affiliation info available
Venables BL
No affiliation info available
Roongta V
No affiliation info available

MeSH

AlkylationElectronsEthersIsatinMagnetic Resonance SpectroscopyMolecular StructureNitrogen IsotopesNitrogen OxidesOximesReference StandardsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20818803

Citation

Liu, Xiaohong, et al. "15N Chemical Shifts of a Series of Isatin Oxime Ethers and Their Corresponding Nitrone Isomers." Magnetic Resonance in Chemistry : MRC, vol. 48, no. 11, 2010, pp. 873-6.
Liu X, Huang XS, Sin N, et al. 15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers. Magn Reson Chem. 2010;48(11):873-6.
Liu, X., Huang, X. S., Sin, N., Venables, B. L., & Roongta, V. (2010). 15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers. Magnetic Resonance in Chemistry : MRC, 48(11), 873-6. https://doi.org/10.1002/mrc.2680
Liu X, et al. 15N Chemical Shifts of a Series of Isatin Oxime Ethers and Their Corresponding Nitrone Isomers. Magn Reson Chem. 2010;48(11):873-6. PubMed PMID: 20818803.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers. AU - Liu,Xiaohong, AU - Huang,Xiaohua Stella, AU - Sin,Ny, AU - Venables,Brian L, AU - Roongta,Vikram, PY - 2010/9/7/entrez PY - 2010/9/8/pubmed PY - 2011/2/10/medline SP - 873 EP - 6 JF - Magnetic resonance in chemistry : MRC JO - Magn Reson Chem VL - 48 IS - 11 N2 - In this article, we describe the characteristic (15)N chemical shifts of isatin oxime ethers and their isomer nitrone. These oxime ethers and nitrones are the alkylation reaction products of isatin oximes. In our study, the (15)N chemical shifts observed in these oxime ethers were in the 402-408 (or 22-28) ppm range, although those for their corresponding nitrone series were in the 280-320 (or -100 to -60) ppm range. This remarkable difference in (15)N NMR chemical shift values could potentially be used to determine the O- versus N-alkylation of oximes, even when only one isomer is available. In this paper, the differences in (15)N NMR chemical shifts serve as the basis for a discussion about how to distinguish both regioisomers derived from the oximes alkylation. SN - 1097-458X UR - https://www.unboundmedicine.com/medline/citation/20818803/15N_chemical_shifts_of_a_series_of_isatin_oxime_ethers_and_their_corresponding_nitrone_isomers_ L2 - https://doi.org/10.1002/mrc.2680 DB - PRIME DP - Unbound Medicine ER -