Triazene

About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.

An exploratory ab initio study of the SN2 reaction of 1,3,3-trimethyltriazene with halide ions

Abstract: Methyltriazene and the O6 oxygen of guanine are believed to undergo a bimolecular nucleophilic substitution (SN2) reaction to form methylguanine, which is proposed to be responsible for the cytotoxic properties of triazene-containing anti-neoplastic agents, such as Dacarbazine. To better understand the proposed mechanism of triazene-containing anti-neoplastic agents, a series of ab initio studies investigating the SN2 reaction between methyltriazenes and halide ions were undertaken. The results of our investigation of the SN2 reaction between 1,3,3-trimethyltriazene and the halide ions are presented here.Key words: triazene, trimethyltriazene, Dacarbazine, Temozolomide, bimolecular nucleophilic substitution reaction.

trans-Bis[1,3-bis-(2-methoxy-phen-yl)triazenido]dimethano-lcadmium(II).

Abstract: In the title compound, [Cd(C14H14N3O2)2(CH3OH)2], each cadmium(II) center is six-coordinated by an N atom and an O atom of two 1,3-bis­(2-methoxy­phen­yl)triazene ligands and by the O atoms of two methanol mol­ecules. The distorted octa­hedral coordination geometry of the Cd atom has two N and two O atoms in the equatorial plane, and two O atoms in axial positions. The complex is stabilized by intra­molecular O—H⋯O and O—H⋯N hydrogen bonds. In the crystal structure the complexes are linked into chains via inter­molecular C—H⋯π stacking inter­actions. One of the methanol C atoms is disordered with ouccupancies of 0.7:0.3.

Darstellung und Eigenschaften des Tribrom-cyclo-1λ6-wolfram-3,5-dithia-2,4,6-triazens/Synthesis and Properties of Tribromo-cyclo-1λ6-tungsten-3,5-dithia-2,4,6-triazene

Abstract: The metallacycle [Br₃WS₂N₃] has been obtained from the reaction of S₄N₄ with WBr₅. The salt [Ph₄P⁺][Br₄WS₂N₃⁻] was formed from [Br₃WS₂N₃] by addition of Ph₄PBr. It crystallizes in the orthorhombic space group Pbca with a = 1396.8(4), b = 1961.9(5), c = 2108.0(4) pm, and Z = 8. The following mean bond lengths were observed in the anion: W-N 184.2, W-Br 256.8, N-S 157.8 pm.

Triazene drug metabolites. Part 12. Base catalysed formation of 3-alkyl-1-aryltriazenes from 3-alkyl-3-hydroxymethyl-1-aryltriazenes

Abstract: 3-Alkyl-3-hydroxymethyl-1-aryltriazenes are stable in aprotic solvents, but decompose in non-aqueous protic solvents to the corresponding 3-alkyl-1-aryltriazenes. The reactions are catalysed by the presence of bases, and the catalytic activity of the base depends upon its aqueous pKa. A Bronsted plot of the catalytic rate constant, kB, versus base pKa gives rise to a Bronsted β value of 1.1. Tertiary bases have no catalytic effect. The deuterium isotope effect for the piperidine catalysed reaction is ca. 1.4. The catalytic rate constants kB depend upon the triazene structures, increasing with the size of the 3-alkyl group (Pr > Et > Me) and with electron-withdrawing ability of the substituent in the 1-aryl group (Cl > H > MeO). The observations are rationalised in terms of a six-membered transition state involving the N–CH2–OH group of the triazene and the N–H of the base and in which proton transfer from the hydroxy group to the nitrogen atom of the catalyst is extensive. In mixed aqueous–ethanol solvents tertiary bases also have a catalytic effect. A Bronsted β value of 0.67 and a solvent deuterium isotope effect of 1.18 identify the proton as ca. 70% transferred to the base in the transition state. In no reaction was aminomethylation of the base observed.