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Superbases in the gas phase. Part II. Further extension of the basicity scale using acyclic and cyclic guanidines
Author(s) -
Raczyńska E. D.,
Maria P.C.,
Gal J.F.,
Decouzon M.
Publication year - 1994
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610071211
Subject(s) - chemistry , superbase , acetonitrile , solvation , phosphazene , affinities , intramolecular force , proton affinity , hydrogen bond , ionic bonding , proton , gas phase , phase (matter) , inorganic chemistry , organic chemistry , solvent , stereochemistry , molecule , ion , catalysis , physics , protonation , quantum mechanics , polymer
The superbase gas‐phase scale has been further extended up to proton affinities of ca 1080 kJ mol −1 by use of cyclic and acyclic guanidines 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 on basicity are discussed. From a correlation p K a (acetonitrile) vs gas‐phase basicity, proton affinity values in the range 1070–1410 kJ mol −1 are predicted for Schwesinger phosphazene compounds.