Anomalous 1H NMR chemical shift behavior of substituted benzoic acid esters

Vidya Gadikota, Rajeshwar Reddy Govindapur, D. Srinivas Reddy, Hailey J. Roseman, R. Thomas Williamson, Jeffrey G. Raab

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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 languageEnglish
Pages (from-to)248-252
Number of pages5
JournalMagnetic Resonance in Chemistry
Volume61
Issue number4
DOIs
StatePublished - Apr 2023

Keywords

  • H
  • NMR
  • benzoic acid esters
  • density functional theory (DFT)

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