Proton Fingerprints Portray Molecular Structures: Enhanced Description of the¹H NMR Spectra of Small Molecules

Abstract

The characteristic signals observed in NMR spectra encode essential information on the structure of small molecules. However, extracting all of this information from complex signal patterns is not trivial. This report demonstrates how computer-aided spectral analysis enables the complete interpretation of 1D 1H NMR data. The effectiveness of this approach is illustrated with a set of organic molecules, for which replicas of their 1H NMR spectra were generated. The potential impact of this methodology on organic chemistry research is discussed.

Digital NMR Profiles as Building Blocks: Assembling 1H Fingerprints of Steviol Glycosides

“…Although HiFSA fingerprinting can be carried out in a variety of deuterated solvents, 3 DMSO- d 6 was selected for this study because it provides several practical advantages, including good signal dispersion in the 1D 1 H NMR spectra and access to exchangeable protons, which facilitates the overall assignment process. Despite its well-known shortcomings (e.g., it is difficult to remove, highly viscous, and hygroscopic), the fact that many organic substances are soluble in DMSO- d 6 makes this solvent a widely suitable option for small-molecule NMR analysis.…”

Absolute Configuration of Native Oligomeric Proanthocyanidins with Dentin Biomodification Potency

“…24,36 The final optimized 1 H NMR spectral parameters of 3 – 6 are attached as tabulated HiFSA profiles in the PERCH .pms file format (Tables S30–S33 in the Supporting Information). Chemical shifts ( δ H in ppm) and coupling constants ( J in Hz) are reported with four and two decimal place precision, respectively.…”

Computer‐assisted 1H NMR analysis of the anti‐tuberculosis drug lead ecumicin

“…However, the resulting structure was similar to the X‐ray structure of 1 (Supporting Information), suggesting that the conformation of ecumicin is relatively rigid, with the main flexibility involving the three amino acid tail. Although the ACA graphical user interface of the PERCH NMR software has been successfully used to analyze the 1 H NMR spectra of many molecules in a semi‐automated or fully automated manner, including the nonapeptide atosiban, it was not possible to analyze the NMR spectrum of 1 in an unattended process. This may be in part due to the large number of nuclei that must be simultaneously assessed, which increases dramatically the number of potential solutions to be evaluated by the iteration software.…”