Esters nuclear magnetic resonance spectra

If the unknown, neutral, oxygen-containing compound does not give the class reactions for aldehydes, ketones, esters and anhydrides, it is probably either an alcohol or an ether. Alcohols are readily identified by the intense characteristic hydroxyl adsorption which occurs as a broad band in the infrared spectrum at 3600-3300 cm-1 (O—H str.). In the nuclear magnetic resonance spectrum, the adsorption by the proton in the hydroxyl group gives rise to a broad peak the chemical shift of which is rather variable the peak disappears on deuteration. 

In general, on reaction with lithium aluminum hydride, secondary sulfonic esters are desulfonylated, with formation of the corresponding secondary alcohol. An exception is provided in an observation by Reist and coworkers, who treated 6-0-benzoyl-l,2-0-isopropyli-dene-5-O-p-tolylsulfonyl-a-D-glucofuranose, with lithium aluminum hydride in ether and obtained a product thought to be 6-deoxy-l,2-0-isopropylidene-y3-L-idofuranose, derived from an intermediate 5,6-anhydro-L-ido derivative later, Ryan and coworkers showed, from its nuclear magnetic resonance spectrum, that the product was 5-deoxy-l,2-0-isopropylidene-a-D- t/Zo-hexofuranose. The problem has been re-examined by Overend and coworkers the repetition experiment under the conditions of Reist and coworkers afforded 5-deoxy-... 

The structures of vanicosides A (1) and B (2) and hydropiperoside (3) were established primarily by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy techniques and fast atom bombardment (FAB) mass spectrometry (MS).22 The presence of two different types of phenylpropanoid esters in 1 and 2 was established first through the proton (4H) NMR spectra which showed resonances for two different aromatic substitution patterns in the spectrum of each compound. Integration of the aromatic region defined these as three symmetrically substituted phenyl rings, due to three p-coumaryl moieties, and one 1,3,4-trisubstituted phenyl ring, due to a feruloyl ester. The presence of a sucrose backbone was established by two series of coupled protons between 3.2 and 5.7 ppm in the HNMR spectra, particularly the characteristic C-l (anomeric) and C-3 proton doublets... 

This compound exhibits a three-proton singlet in its nuclear magnetic resonance (NMR) spectrum at 5 = 3.6, typical for a methyl ester. Its molecular weight is 104, and a strong fragment peak is seen at m/z 86. 

A potassium bromide pellet prepared from the major component indicated the formation of an ester linkage, the presence of a phosphate, and an A -t-butoxycarbonyl group. A UV spectrum with a maximum absorption at 257.5 nm identical to that of ATP eliminated the possibility that aminoacylation may have taken place at 6-amino group of nucleotide. Nuclear magnetic resonance spectroscopy demonstrated the presence of tertiary butyl protons. On the basis of the above evidence, structure (II) has been assigned to this product. 

---