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Dynamic NMR Study and Detailed 1H and 13C Assignments of an ADAR Precursor in Solvent

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Abstract

A nitrogen-containing compound, named methyl-4-phenyl-2-(2,4,6-triisopropyl-phenylsulfonamido)but-3-enoate (MPSN), is used as a precursor for inverse-electron-demand aza-Diels–Alder reaction. Its 1H and 13C nuclear magnetic resonances (NMR) were fully assigned by a combination of one- and two-dimensional NMR experiments. It was found that this compound had two conformers (a and b) in the process of assignments. Exchange spectroscopy (EXSY) was used to study the exchange dynamics of this compound in solvent. On the basis of 1H NMR and EXSY experiments at various temperatures, thermodynamic and dynamic parameters of the conformational exchange process were deduced for this compound. The free-energy activation (ΔG ≠) at 298 K is 15.07 ± 0.6 kcal mol−1, which suggests that the conformational exchange might be the result of C=N bond rotation.

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Acknowledgments

Financial support from the State Key Laboratory Foundation of Magnetic Resonance and Atomic and Molecular Physics (T152906) is gratefully acknowledged. MPSN was kindly provided by Prof. Wenjing Xiao from College of Chemistry of Central China Normal University.

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Authors and Affiliations

  1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, 430079, Hubei, People’s Republic of China

    Chenchen Liu, Liangqiu Lu, Wenjing Xiao, Xiaopeng Liu & Fang Li

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  1. Chenchen Liu
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  2. Liangqiu Lu
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  3. Wenjing Xiao
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  4. Xiaopeng Liu
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  5. Fang Li
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Correspondence to Fang Li.

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Liu, C., Lu, L., Xiao, W. et al. Dynamic NMR Study and Detailed 1H and 13C Assignments of an ADAR Precursor in Solvent. Appl Magn Reson 39, 309–318 (2010). https://doi.org/10.1007/s00723-010-0160-x

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  • DOI: https://doi.org/10.1007/s00723-010-0160-x

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