SUPERBASES IN THE GAS-PHASE .2. FURTHER EXTENSION OF THE BASICITY SCALE USING ACYCLIC AND CYCLIC GUANIDINES

Authors
RACZYNSKA ED MARIA PC GAL JF DECOUZON M
Citation
Ed. Raczynska et al., SUPERBASES IN THE GAS-PHASE .2. FURTHER EXTENSION OF THE BASICITY SCALE USING ACYCLIC AND CYCLIC GUANIDINES, Journal of physical organic chemistry, 7(12), 1994, pp. 725-733
Citations number
65
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
7
Issue
12
Year of publication
1994
Pages
725 - 733
Database
ISI
SICI code
0894-3230(1994)7:12<725:SITG.F>2.0.ZU;2-Z
Abstract
The superbase gas-phase scale has been further extended up to proton a ffinities of ca 1080 kJ mol(-1) by use of cyclic and acyclic guanidine s and vinamidines. Structural features such as Y-conjugation, vinylogy and intramolecular ionic hydrogen bonding leading to their superbasic behaviour are analysed. Solvation effects by water and acetonitrile o n basicity are discussed. From a correlation pK(a)(acetonitrile) vs ga s-phase basicity, proton affinity values in the range 1070-1410 kJ mol (-1) are predicted for Schwesinger phosphazene compounds.