Intramolecular ion solvation effects on gas-phase acidities and basicities. A new stereochemical probe in mass spectrometry

Stereochemical differentiation of cyclic glycols by ion-molecule reactions in a quadrupole mass spectrometer using dimethyl ether acetonitrile and 2-S-pyrrolidinemethanol

“…There are many examples of investigations concerning stereochemical effects for cyclic diols in positive chemical ionization (PCI) with ammonia or isobutane as the reagent gas 5–9. They can serve as model compounds for more complex natural products that contain multiple hydroxy groups such as sugars, steroids and prostaglandins.…”

“…Cis ‐ and trans ‐1,2‐cyclohexanediols have quite similar PCI spectra because of the flexibility of the cyclohexane ring that minimizes stereochemical preferences for proton bridging 5–7…”

Diastereochemical differentiation of bicyclic diols using metal complexation and collision‐induced dissociation mass spectrometry

“…Although trinorbornanediol stereoisomers give rise to identical spectra, the ionized positional isomers can be distinguished from each other 1, 2. However, chemical ionization (CI) and ion/molecule reaction mass spectrometry combined with collision‐induced dissociation (CID) studies have been used to differentiate some diastereoisomeric cyclic diols and trinorbornanediols successfully 1–4, 8–14. For different diastereochemical trinorbornanediols and camphanediols, several reactant gases have been used, including methane, isobutane, ammonia, acetone, trimethyl borate and trimethyl phosphate 1–4.…”

Ion–molecule reactions in the gas phase. Collision energy influence on the competitive S N i/S N 2 orientation from adduct ions of epimeric 1,2‐indanediols prepared by ammonia chemical ionization

“…From previous measurements, the proton affinities of cis bifunctional epimers have been shown to be higher than those of the trans isomers. [38][39][40] Such proton transfer reactions, from selected even-electron charged molecular species of various substrates to neutral reagents like methyl, di-and trimethylamines in a quadrupole collision cell, have been already used to provide information complementary to that obtained under CI conditions. 27 Ion-molecule reactions produced in a low-energy collision cell from a selected ion allow assignment of a specific structure according to its reactivity.…”