Substituent Effects on the Thermal Cis-to-Trans Isomerization of 1,3-Diphenyltriazenes in Aqueous Solution

Chen, Nan; Barra, Mónica; Lee, Ivan; Chahal, Navjot

doi:10.1021/jo011094d

Cited by 33 publications

(31 citation statements)

References 21 publications

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“…1 Triazenes compounds, characterized by having a diazoamino group (-N=N-N<), commonly adopt a trans configuration in the ground state. 2,3 In this paper, we show the crystal structure of a new triazene ligand (triazene 1,3-di(2-methoxyphenyl) (Fig. 1).…”

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confidence: 97%

Crystal Structure of Triazene-1,3-di(2-methoxyphenyl)

Rofouei¹,

Shamsipur

Payehghadr³

2006

Anal. Sci. X

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Aryl triazenes have been studied for over 130 years concerning their interesting structural, anticancer, and reactivity properties. They have been used in medicinal, combinatorial chemistry, in natural synthesis and as organometalic ligands. 1 Triazenes compounds, characterized by having a diazoamino group (-N=N-N<), commonly adopt a trans configuration in the ground state. 2,3 In this paper, we show the crystal structure of a new triazene ligand (triazene 1,3-di(2-methoxyphenyl) (Fig. 1).The compound was prepared by the following method: A 1 liter flask was charged with 100 g of ice and 150 ml of water and then cooled to 0˚C in an ice-bath. To this was added 12.30 g (0.10 mol) of o-anisidine and 13 g (0.13 mol) of hydrochloric acid (d = 1.18 g/ml). To this solution was added a solution of NaNO2 containing 4.10 g (0.06 mol) in 25 ml of water during a 15 min period. After mixing for 15 min a solution containing 14.76 g (0.18 mol) of sodium acetate in 45 ml of water was added. After mixing for 45 min the brown product was filtered and dissolved in Et2O, and was crystallized in a freezer. Yield, 50% (6.85 g). Recrystallization from Et2O afforded the product as an orange crystalline material. M. P. 95 -97˚C.The crystal structure of triazene-1,3-di(2-methoxyphenyl) was solved by direct methods and refined by full-matrix least squares using the program SHELXTL-98. 4 The H atoms were refined isotropically. The molecular structure of crystalline triazene-1,3-di(2-methoxyphenyl) is presented in Fig. 2

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confidence: 97%

Crystal Structure of Triazene-1,3-di(2-methoxyphenyl)

Rofouei¹,

Shamsipur

Payehghadr³

2006

Anal. Sci. X

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“…For aryl triazenes, their structural properties and metal complexes see: Meldola & Streatfield (1888); Leman et al (1993); Chen et al (2002); Vrieze & Van Koten (1987). For a similar structure with cyano instead of ethoxy groups, see: Melardi et al (2008).…”

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confidence: 99%

3-(2-Ethoxyphenyl)-1-(3-nitrophenyl)triaz-1-ene

et al. 2011

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The title compound, C14H14N4O3, exhibits a trans geometry about the N=N double bond in the triazene unit. The molecule is approximately planar (r.m.s. deviation = 0.044 Å for all non-H atoms). An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, C—H⋯N hydrogen bonds lead to the formation of dimers which are, in turn, connected to each other by C—H⋯O hydrogen bonds, forming infinite chains of R 2 2(8) graph-set motif.

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“…1,3-Diphenyltriazene and 1,3-bis-(4-methoxyphenyl)-triazene employed were existing samples from a previous study [8]. Methanol and acetonitrile (OmniSolv grade; EM Science, Gibbstown, NJ), 2-hydroxypropyl-β-cyclodextrin (FW = 2,354), α-cyclodextrin, and β-cyclodextrin (Aldrich, St. Louis, MO), permethyl-β-cyclodextrin (TCI, Portland, OR), soluble starch (Baker, Phillipsburg, NJ), and D-glucose (EM Science) were used as received.…”

Section: Experimental Reagentsmentioning

confidence: 99%

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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Substituent Effects on the Thermal Cis-to-Trans Isomerization of 1,3-Diphenyltriazenes in Aqueous Solution

Cited by 33 publications

References 21 publications

Crystal Structure of Triazene-1,3-di(2-methoxyphenyl)

Crystal Structure of Triazene-1,3-di(2-methoxyphenyl)

3-(2-Ethoxyphenyl)-1-(3-nitrophenyl)triaz-1-ene

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

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