✦ LIBER ✦

Uncommon electronic effects on the gas-phase Brønsted acidity of isomeric hydroxyphenylium ions

✍ Scribed by Felice Grandinetti; Maurizio Speranza

Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 567 KB
Volume: 229
Category: Article
ISSN: 0009-2614
DOI: 10.1016/0009-2614(94)01102-8

No coin nor oath required. For personal study only.

✦ Synopsis

The Brsnsted-acid properties of gaseous hydroxyphenylium ions have been evaluated by kinetic FT-ICR experiments and compared with ab initio theoretical predictions. While ortho and para HOC,H$ ions do not show any significant reactivity, the meta HO&H,+ isomer exhibits a pronounced Bmnsted-acid character by releasing efficiently to NH3 its HO proton instead of one of its more acidic ring protons adjacent to the formally vacant orbital. This peculiar behavior derives from extensive p-n: conjugative stabilization in meta -0C 6 H+ 4 , absent in the ortho and para isomers, and to the operation of a substantial activation barrier ( 3 46 kJ mol-' ) in the ring-proton transfer reactions from arylium ions.

📜 SIMILAR VOLUMES

ChemInform Abstract: Quantum Chemical An

ChemInform Abstract: Quantum Chemical Analysis of para-Substitution Effects on the Electronic Structure of Phenylnitrenium Ions (I) in the Gas Phase and Aqueous Solution

✍ Michael B. Sullivan; Kenneth Brown; Christopher J. Cramer; Donald G. Truhlar 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 27 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

The gas phase ion chemistry of the acety

The gas phase ion chemistry of the acetyl cation and isomeric [C2H3O]+ ions. On the structure of the [C2H3O]+ daughter ions generated from the enol of acetone radical cation

✍ Peter C. Burgers; John L. Holmes; Jan E. Szulejko; Alexander A. Mommers; Johan K 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 English ⚖ 931 KB

Leaving group effects on the selectivity

Leaving group effects on the selectivity of the gas-phase fragmentation reactions of side chain fixed-charge-containing peptide ions

✍ Kade D. Roberts; Gavin E. Reid 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 890 KB

## Abstract The effect of trialkylsulfonium __versus__ quaternaryalkylammonium ions on the multistage gas‐phase fragmentation reactions of side chain, fixed‐charge, cysteine‐containing peptides has been examined in a quadrupole linear ion trap. These tandem mass spectrometry experiments reveal that

ChemInform Abstract: Chiral Ions in the

ChemInform Abstract: Chiral Ions in the Gas Phase. Part 7. Wagner—Meerwein Rearrangements in the Gas Phase: Deuterium Isotope Effects on Acid-Induced Dissociation of Optically Active Phenylpropanols.

✍ Maurizio Speranza; Antonello Filippi 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 25 KB 👁 2 views