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Ambident Reactivity of the Cyanate Anion
Author(s) -
Schaller Heike F.,
Schmidhammer Uli,
Riedle Eberhard,
Mayr Herbert
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800314
Subject(s) - carbocation , cyanate , reactivity (psychology) , ion , chemistry , diffusion , charge (physics) , computational chemistry , medicinal chemistry , polymer chemistry , organic chemistry , physics , thermodynamics , particle physics , medicine , alternative medicine , pathology
Carbocations attack preferentially at the nitrogen terminus of the cyanate anion (see scheme), not at oxygen, the “hard” terminus with the highest charge density. Kinetic investigations show that carbocations which are less stabilized than Ph 3 C + undergo diffusion‐controlled reactions with OCN − and therefore cannot be treated by the transition‐state theory.