Griess, Peter

Peter Griess synthesized the first azo dye soon after his discovery of the diazotization reaction in 1858. The two reactions which form the basis for azo dye chemistry are diazotization (eq. 1) and coupling (eq. 2) (2). 

In the modern formulation, but ignoring the quinone diazide mesomerism (see Sec. 4.2), his diazotization is shown in Scheme 1-1 yielding 1.2. For the centenary of the discovery of diazo compounds Wizinger (1958) and Cliffe (1959) wrote accounts of its history. More recently Zahn (1989) summarized the life and work of Peter Griess. 

In the historical introduction to this book (Sec. 1.1) it was mentioned that the discoverer of diazo compounds, Peter Griess, realized quite early (1864 a) that these species could react with alkali hydroxides. Thirty years later Schraube and Schmidt (1894) found that the primary product from the addition of a hydroxide ion to a diazo compound can isomerize to form a secondary product. In this section we will discuss the equilibria of the first acid-base process of aromatic diazonium ions. In the following section additional acid-base reactions will be treated in connection with the isomerism of addition products of hydroxide ions to diazonium ions. 

Undoubtedly the most significant discovery in colour chemistry in the post-Mauveine period was due to the work of Peter Griess, which provided the foundation for the development of the chemistry of azo dyes and pigments. In 1858, Griess demonstrated that the treatment of an aromatic amine with nitrous acid gave rise to an unstable salt (a dia-zonium salt) which could be used to prepare highly coloured compounds. 

Shortly after Perkin had produced the first commercially successful dyestuff, a discovery was made which led to what is now the dominant chemical class of dyestuffs, the azo dyes. This development stemmed from the work of Peter Griess, who in 1858 passed nitrous fumes (which correspond to the formula N203) into a cold alcoholic solution of 2-aminO 4,6 dinitrophenol (picramic acid) and isolated a cationic product, the properties of which showed it to be a member of a new class of compounds [1]. Griess extended his investigations to other primary aromatic amines and showed his reaction to be generally applicable. He named the products diazo compounds and the reaction came to be known as the diazotisation reaction. This reaction can be represented most simply by Scheme 4.1, in which HX stands for a strong monobasic acid and Ar is any aromatic or heteroaromatic nucleus. 

Heines, JChemEd 35, 187—91 (1958) (Peter Griess-Discoverer of Diazo Compounds)... 

The ability of copper(I) and silver(I) salts to react with triazenes was first noted by Peter Griess in 1866 (90), and triazenide complexes of these metals have attracted considerable attention during the intervening years. In marked contrast the first gold triazenide complexes have only recently been reported. 

Tile diazo compound of picramic acid was the first diazonium compound discovered and led to the important work of Peter Griess. 

Peter Griess, 1858.—Diazo compounds were discovered and first prepared by Peter Griess in 1858. The historical method used by him is the same in general as is now used widely in dyestuff manufacture. It has already been described and consists in the action of nitrous acid on an aromatic primary amine, e.g., aniline. When this reaction takes place, at ordinary or slightly raised temperatures, the same products are obtained as with aliphatic primary amines, viz., the hydroxyl compound of the hydrocarbon radical, free nitrogen and water. 

In 1858 Peter Griess (in time taken from his duties in an English brewery) discovered diazonium salts. In 1875 Emil Fischer (at the University of Munich) found that reduction of benzenediazonium chloride by sulfur dioxide yields phenylhydrazine. Nine years later, in 1884, Fischer reported that the phenylhydrazine he had discovered could be used as a powerful tool in the study of carbohydrates. 

As already mentioned, under the preparation of methyl amine, the behaviour of the aliphatic primary amines toward nitrous add is very different from that of the aromatic compounds. While the former yield alcohols with the elimination of nitrogen, the latter, in a mineral acid solution, under the influence of nitrous add, yield diazo-compounds, discovered by Peter Griess, in the form of thdr mineral add salts. 

In 1858 a discovery of outstanding importance w as made by Peter Griess, a chemist in a Burton-on-Trent brewery. He brought to light what was known as the diazo reaction. When aromatic primary amines are treated w ith nitrous acid (produced by the action of hydrochloric acid on sodium nitrite) they form diazonium salts as illustrated in the equation CeH NH +HCL + HNOa = CeHjN.Na+ 2H,0. 

II Epilogue From Peter Griess Discovery to Organometallic Diazo Compounds... 

Soon after his return to London, Foster reported favorably for the Repertoire on Peter Griess s research on diazo compounds at the Royal College of Chemistry, but he took issue with Griess s assumption that the atomicity of nitrogen could vary. "The idea of atomicity, or capacity of combination," he wrote, "is a property of elementary atoms just... 

After organic azides were discovered by Peter Griess more than 140 years ago, numerous appHcations have been developed. Particularly in more recent times, completely new perspectives have been developed for their use in peptide and combinatorial chemistry as well as in heterocyclic synthesis. In this non-comprehensive review [2-4], the fundamental characteristics of azide cycloaddition chemistry and current developments in life and material sciences are presented. 

Peter Griess, a student of August Wilhelm v. Hofmann, living in England, discovered diazotization in 1857. In 1861, the first azo-dye, aniline yellow (Solvent Yellow 1) appeared on the market in England a further milestone in the development of azo-dyes was Congo red, a substantive dye discovered by Paul Bottiger in 1884. 

In this case the nitrogen atoms have the opportunity, Blomstrand stated, of forming nitrogen gas, N, instead of NO. At low temperatures, however, they prefer, as Peter Griess had found in 1858, to form "diazoamidobenzol" with a chain of 3-valent nitrogen atoms ... 

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