Kinetics of splitting and deprotonation equilibria of monosubstituted and symmetrically disubstituted diaryltriazenes

Beneš, Jan; Beránek, V.; Zimprich, J.; Vetešník, P.

doi:10.1135/cccc19770702

Cited by 15 publications

(12 citation statements)

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“…The prepared triazenes 1 are characterised by their stabilities in acid medium, which is unusual for triazene derivatives 8. They are cleaved only very slowly in acid media.…”

Section: Resultsmentioning

confidence: 99%

Structure and Reactivity of 3,3‐Disubstituted 1‐(5‐Nitro‐2,1‐benzisothiazol‐3‐yl)triazenes

et al. 2003

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The reaction between 5‐nitro‐2,1‐benzisothiazole‐3‐diazonium species and N‐substituted anilines produces the 1‐(5‐nitro‐2,1‐benzisothiazol‐3‐yl)‐3,3‐disubstituted triazenes 1. These triazenes are highly stable, and even in strongly acidic medium (0.5 mol⋅L−1 H2SO4) they are only slowly decomposed back to the diazonium ion and substituted anilinium ion (for the N‐ethyl derivative in 0.5 mol·L−1 H2SO4 at 25 °C, t1/2 ≈︁ 7 h). A series of six triazenes were characterised by their 1H and 13C NMR spectra and mass spectra. Two of the triazenes were also identified by X‐ray crystallography. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…The prepared triazenes 1 are characterised by their stabilities in acid medium, which is unusual for triazene derivatives 8. They are cleaved only very slowly in acid media.…”

Section: Resultsmentioning

confidence: 99%

Structure and Reactivity of 3,3‐Disubstituted 1‐(5‐Nitro‐2,1‐benzisothiazol‐3‐yl)triazenes

et al. 2003

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“…Acid-promoted decomposition of aryltriazenes dissolved in aqueous media typically involves general acid catalysis (A-S E 2) [10] or specific acid catalysis (A1) [8,11]. Decomposition of 1, under experimental conditions analogous to those of this study, has been found to follow an A1 mechanism (Scheme 1), as rates increase with decreasing pH and are independent of the buffer concentration [12].…”

Section: Resultsmentioning

confidence: 98%

Inhibition of acid‐induced decomposition of diphenyltriazenes by complexation with cyclodextrins

Asadi

Barra

2010

Int J of Chemical Kinetics

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Acid-promoted N N bond cleavage in 1,3-diphenyltriazenes (X-Ph-N=N-NH-Ph-X; X = H, 4-OCH 3 ), leading to formation of diazonium ions and anilines, is strongly inhibited in aqueous solutions in the presence of cyclodextrins (CDs). The inhibition is ascribed to the formation of inclusion complexes that render the guest diphenyltriazene significantly less basic as a result of the less polar nature of the CD cavity (a microsolvent effect). Association equilibrium constants for 1:1 host-guest complexes increase in the order α-CD <β-CD ∼ permethyl-β-CD < hydroxypropyl-β-CD, with values for X = 4-OCH 3 being larger than those for X = H. In the case of α-CD, formation of 2:1 host-guest complexes is also involved. C

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“…The reference compounds used for comparison are 1-aryl-3,3-dimethyltriazenes [22][23][24]. The bond lengths calculated for compounds 1a-1f for Csp2-N at the HF level range from 1.412 to 1.415 Å, at the B3LYP level from 1.410 to 1.414 Å, and those of the references range from 1.415 to 1.433 Å.…”

Section: Molecular Structure Of Triazenesmentioning

confidence: 99%

DFT, ab initio and FT-IR studies of the structure of sulfonamide triazenes

Dabbagh

Teimouri

Shiasi

et al. 2008

JICS

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We present an in-depth investigation of the structural, infrared spectra and visible spectra of various triazenes with a sulfonamide moiety. The preparation of 4-sulfonyl amide benzenediazonium chloride with cyclic amines of various ring sizes (pyrrolidine, piperidine, 4-methylpiperidine, N-methylpiperazine, morpholine and hexamethyleneimine) are theoretically investigated using the density functional theory (DFT) and Hartree-Fock (HF) levels of theory with the standard 6-31G* basis set. The calculated vibrational frequencies are evaluated via comparison with experimental values. The vibrational spectral data obtained from solid-phase FT-IR spectra are assigned modes based on the results of the theoretical calculations. The UV-Vis spectrum of each compound is measured in various solvents with a wide range of polarity to examine the role of solvent chemistry on observed spectral changes. The calculated spectra are in good agreement with the experimental spectra.

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Kinetics of splitting and deprotonation equilibria of monosubstituted and symmetrically disubstituted diaryltriazenes

Cited by 15 publications

References 0 publications

Structure and Reactivity of 3,3‐Disubstituted 1‐(5‐Nitro‐2,1‐benzisothiazol‐3‐yl)triazenes

Structure and Reactivity of 3,3‐Disubstituted 1‐(5‐Nitro‐2,1‐benzisothiazol‐3‐yl)triazenes

Inhibition of acid‐induced decomposition of diphenyltriazenes by complexation with cyclodextrins

DFT, ab initio and FT-IR studies of the structure of sulfonamide triazenes

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