Abstract
Benzoic acid esters represent key building blocks for many drug discovery and development programs and have been advanced as potent PDE4 inhibitors for inhaled administration for treatment of respiratory diseases. This class of compounds has also been employed in myriad industrial processes and as common food preservatives. Recent work directed toward the synthesis of intermediates for a proprietary medicinal chemistry program led us to observe that the 1H NMR chemical shifts of substituents ortho to the benzoic acid ester moiety defied conventional iterative chemical shift prediction protocols. To explore these unexpected results, we initiated a detailed computational study employing density functional theory (DFT) calculations to better understand the unexpectedly large variance in expected versus experimental NMR chemical shifts.
Original language | English |
---|---|
Pages (from-to) | 248-252 |
Number of pages | 5 |
Journal | Magnetic Resonance in Chemistry |
Volume | 61 |
Issue number | 4 |
DOIs | |
State | Published - Apr 2023 |
Keywords
- H
- NMR
- benzoic acid esters
- density functional theory (DFT)
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Gadikota, V., Govindapur, R. R., Reddy, D. S., Roseman, H. J., Williamson, R. T. (2023). Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters. Magnetic Resonance in Chemistry, 61(4), 248-252. https://doi.org/10.1002/mrc.5326
Gadikota, Vidya ; Govindapur, Rajeshwar Reddy ; Reddy, D. Srinivas et al. / Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters. In: Magnetic Resonance in Chemistry. 2023 ; Vol. 61, No. 4. pp. 248-252.
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title = "Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters",
abstract = "Benzoic acid esters represent key building blocks for many drug discovery and development programs and have been advanced as potent PDE4 inhibitors for inhaled administration for treatment of respiratory diseases. This class of compounds has also been employed in myriad industrial processes and as common food preservatives. Recent work directed toward the synthesis of intermediates for a proprietary medicinal chemistry program led us to observe that the 1H NMR chemical shifts of substituents ortho to the benzoic acid ester moiety defied conventional iterative chemical shift prediction protocols. To explore these unexpected results, we initiated a detailed computational study employing density functional theory (DFT) calculations to better understand the unexpectedly large variance in expected versus experimental NMR chemical shifts.",
keywords = "H, NMR, benzoic acid esters, density functional theory (DFT)",
author = "Vidya Gadikota and Govindapur, {Rajeshwar Reddy} and Reddy, {D. Srinivas} and Roseman, {Hailey J.} and Williamson, {R. Thomas} and Raab, {Jeffrey G.}",
note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.",
year = "2023",
month = apr,
doi = "10.1002/mrc.5326",
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Gadikota, V, Govindapur, RR, Reddy, DS, Roseman, HJ, Williamson, RT 2023, 'Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters', Magnetic Resonance in Chemistry, vol. 61, no. 4, pp. 248-252. https://doi.org/10.1002/mrc.5326
Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters. / Gadikota, Vidya; Govindapur, Rajeshwar Reddy; Reddy, D. Srinivas et al.
In: Magnetic Resonance in Chemistry, Vol. 61, No. 4, 04.2023, p. 248-252.
Research output: Contribution to journal › Article › peer-review
TY - JOUR
T1 - Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters
AU - Gadikota, Vidya
AU - Govindapur, Rajeshwar Reddy
AU - Reddy, D. Srinivas
AU - Roseman, Hailey J.
AU - Williamson, R. Thomas
AU - Raab, Jeffrey G.
N1 - Publisher Copyright:© 2022 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.
PY - 2023/4
Y1 - 2023/4
N2 - Benzoic acid esters represent key building blocks for many drug discovery and development programs and have been advanced as potent PDE4 inhibitors for inhaled administration for treatment of respiratory diseases. This class of compounds has also been employed in myriad industrial processes and as common food preservatives. Recent work directed toward the synthesis of intermediates for a proprietary medicinal chemistry program led us to observe that the 1H NMR chemical shifts of substituents ortho to the benzoic acid ester moiety defied conventional iterative chemical shift prediction protocols. To explore these unexpected results, we initiated a detailed computational study employing density functional theory (DFT) calculations to better understand the unexpectedly large variance in expected versus experimental NMR chemical shifts.
AB - Benzoic acid esters represent key building blocks for many drug discovery and development programs and have been advanced as potent PDE4 inhibitors for inhaled administration for treatment of respiratory diseases. This class of compounds has also been employed in myriad industrial processes and as common food preservatives. Recent work directed toward the synthesis of intermediates for a proprietary medicinal chemistry program led us to observe that the 1H NMR chemical shifts of substituents ortho to the benzoic acid ester moiety defied conventional iterative chemical shift prediction protocols. To explore these unexpected results, we initiated a detailed computational study employing density functional theory (DFT) calculations to better understand the unexpectedly large variance in expected versus experimental NMR chemical shifts.
KW - H
KW - NMR
KW - benzoic acid esters
KW - density functional theory (DFT)
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U2 - 10.1002/mrc.5326
DO - 10.1002/mrc.5326
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JO - Magnetic Resonance in Chemistry
JF - Magnetic Resonance in Chemistry
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Gadikota V, Govindapur RR, Reddy DS, Roseman HJ, Williamson RT, Raab JG. Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters. Magnetic Resonance in Chemistry. 2023 Apr;61(4):248-252. doi: 10.1002/mrc.5326