79146-10-4Relevant academic research and scientific papers
BORON PHOTOCHEMISTRY. XV. DETERMINATION OF THE HAMMETT SUBSTITUENT CONSTANT FOR THE p-DIMESITYLBORYL GROUP
Glogowski, M. E.,Williams, J.L.R.
, p. 137 - 146 (2007/10/02)
Hammett signal values reflect relative strengths of the combined inductive and resonance effects of substituents.Using the ionization technique, as well as an independent neutralization method, we found the ?H value for the p-dimesitylboryl group to be 0.42 as compared to 0.78 for the p-nitro group.The value of ?uv,H=0.65 +/- 0.03 determined from pi-electron interaction processes, such as absorption spectra and pi complex formation, is felt to relate better to the p-dimesitylboryl-substituted dyes.A similar function reflecting the pi resonance interaction of substituent groups is the Tomasik-Krygowski ?uv,K value, for which 0.58 was found for the p-dimesitylboryl group compared to 0.66 for the p-nitro group.
BORON PHOTOCHEMISTRY XIV. THE DIMESITYLBORYL GROUP AS AN AUXOCHROME IN DYES: THE SYNTHESIS OF para-SUBSTITUTED DIMESITYLBORYLPHENYLAZONAPHTHOL DYES
Glogowski, M. E.,Williams, J.L.R.
, p. 1 - 8 (2007/10/02)
The dimesitylboryl group is a new auxochrome.This group was evaluated by comparison of 4--1-naphthol (III) with 4--1-naphthol (IV) and of the substituted N--1,3-benzenedisulfonamide (VIIIa) with N--1,3-benzenedisulfonamide (VIIIb).The syntheses of 5-hydroxy-8-(4-dimesitylborylphenylazo)-1-naphthyl amine (IX) and α-propionic acid (X) are reported.The visible spectra of the dimesitylboryl-containing dyes and those of the nitro analogs were similar in shape.The spectral shifts of the dimesitylboryl compounds are as great as those of the corresponding nitro analogs.However, the boryl-substituted dyes required a nondonor medium for alkalinity-induced spectral shifts.As an auxochrome the dimesitylboryl group is roughly equivalent to a nitro group.
