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Structure–reactivity correlations for aza‐arenes. Proton affinities, p K a values, hydrogen–deuterium exchange rates and radical‐induced 13 C shifts
Author(s) -
SpangetLarsen Jens
Publication year - 1995
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.610080709
Subject(s) - chemistry , affinities , deuterium , hydrogen–deuterium exchange , proton affinity , reactivity (psychology) , proton , hydrogen , computational chemistry , deuterium nmr , density functional theory , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , atomic physics , protonation , nuclear physics , ion , medicine , physics , pathology , alternative medicine
Molecular reactivity parameters based on the concept of an effective electronic potential and defined as a simple function of the molecular charge distribution were applied in a study of various aspects of the chemical reactivity of azabenzenes and azanaphthalenes. Excellent linear correlations were obtained for proton affinities, p K a values, H–D exchange rate exponents and 13 C shifts induced by the paramagnetic shift reagent TEMPO. In the last case, the predictions for quinazoline prompted a reinvestigation of the 13 C NMR spectrum of this compound, resulting in a reassignment of the spectrum relative to the assignment assumed by Grant and co‐workers.