On the kinetics and energetics of one-electron oxidation of 1,3,5-triazines

Azenha, M. Emília; Burrows, Hugh D.; Coimbra, R. A.; Fernández, M. Isabel; García, M. V.; Rodrigues, A.E.; Santaballa, J. Arturo; Steenken, S.

doi:10.1039/b210119j

Cited by 29 publications

(6 citation statements)

References 15 publications

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“…31 However, the mechanism is unlikely in this case since triazines are known to have very high oxidation potentials. 32 Furthermore, homolytic dissociation is unlikely to be an important mechanism in the case of triazines, since 2-hydroxy products are observed on photolysis of a wide variety of 1,3,5-triazines having very different dissociation energies for the 2-substituent bonds. 21,33 We therefore believe that the main mechanism involves additionelimination.…”

Section: Discussionmentioning

confidence: 99%

Kinetic and mechanistic aspects of the direct photodegradation of atrazine, atraton, ametryn and 2‐hydroxyatrazine by 254 nm light in aqueous solution

Azenha

Burrows

Coimbra

et al. 2003

J of Physical Organic Chem

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Atrazine (1), Atraton (2) and Ametryn (3) are photodegraded upon 254 nm irradiation, yielding 2-OHatrazine (4) as a photoproduct. Dealkylation products are also generated, and 4-ethylamino-6-isopropylamino-(1,3,5)-triazine was also found as a photoproduct of 3. The main photoreaction is proposed to be an addition-elimination, yielding 4, which subsequently photodegrades. The ease of photodegradation depends on the electron availability at position C-2, the observed order of photoreactivity being 1 > 3 > 4 > 2.

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Section: Discussionmentioning

confidence: 99%

Kinetic and mechanistic aspects of the direct photodegradation of atrazine, atraton, ametryn and 2‐hydroxyatrazine by 254 nm light in aqueous solution

Azenha

Burrows

Coimbra

et al. 2003

J of Physical Organic Chem

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“…A possible alternative is direct photodegradation, for which a number of studies on photoproducts have been performed, but little mechanistic information is available. [23][24][25][26][27] Proper modeling of the environmental fate of these agrochemicals will be difficult unless detailed mechanistic understanding becomes available. Indeed, a comprehensive study of the photodegradation process must involve proper knowledge of the nature and role of their different low-lying excited states.…”

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confidence: 99%

On the Low‐Lying Excited States of sym‐Triazine‐Based Herbicides

et al. 2005

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We report a joint computational and luminescence study on the low-lying excited states of sym-triazines, namely, 1,3,5-triazine (1) and the ubiquitous herbicides atrazine [6-chloro-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine (2)] and ametryn [6-methylthio-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine (3)]. Geometrical structures, energetics, and transition and state properties of I and 2 were computed at the TD-DFT, CASSCF, and CASPT2 levels of theory. The fluorescence and phosphorescence emission spectra, lifetimes, and fluorescence quantum yields were measured for the three compounds, and from these, the energies of the lowest excited states and their corresponding radiative rates were determined. The predictions from CASPT2 calculations are in good agreement with the experimental results obtained from the luminescence studies and allow the interpretation of different absorption and emission features.

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“…1,3,5-Triazine ( s -triazine) has been widely used in organic reactions 1–6 and offers access to a multitude of useful molecules 7,8 due to its specific structure and electronic properties. This scaffold has provided the basis for the design of biologically active molecules with diverse therapeutic profiles, 9–13 herbicides, 14,15 and polymer photostabilizers. 16 Some trisubstituted-1,3,5-triazines are also used as liposomes.…”

Section: Introductionmentioning

confidence: 99%

A novel one-dimensional coordination polymer of cadmium(II)/triazine extending by di-chloro and di-iodo bridges

Shahmirzaei

Mardani

Moeini

et al. 2020

Journal of Chemical Research

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A new triazine ligand salt, 2,2′,2″-(1,3,5-triazine-2,4,6-triyl)tris(hydrazin-1-ium) chloride [THT·(HCl)3], and the one-dimensional coordination polymer of cadmium, [Cd2( µ-THT)( µ-Cl)( µ-I)I2]·2(H2O), are prepared and characterized by elemental analysis, Fourier-transform infrared spectroscopy, 1H NMR spectroscopy, and single-crystal X-ray diffraction (for the cadmium polymer). X-ray analysis revealed that the polymeric backbone is extended alternatively by di-iodo and di-chloro bridges; this type of bridge is not observed previously between any metal atoms. There are two types of cadmium atoms in the polymer: cadmium of the polymeric chain and terminal cadmiums. The geometry around the first (CdN2Cl2I2) is octahedral, while the latter (CdN3I2) has an incline to square-pyramidal geometry. The triazine ligand of this structure also bridges two cadmium atoms and acts as an N3 donor toward the terminal cadmium atoms and as an N2 donor toward the cadmium atoms of the chain. In the crystal network of the cadmium polymer, the hydrogen bonds of N–H···X (X: O, N, I) form different hydrogen bond motifs, including [Formula: see text](8), [Formula: see text](10), [Formula: see text](14), [Formula: see text](18), [Formula: see text](20), [Formula: see text](24), [Formula: see text](28), and [Formula: see text](32).

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On the kinetics and energetics of one-electron oxidation of 1,3,5-triazines

Cited by 29 publications

References 15 publications

Kinetic and mechanistic aspects of the direct photodegradation of atrazine, atraton, ametryn and 2‐hydroxyatrazine by 254 nm light in aqueous solution

Kinetic and mechanistic aspects of the direct photodegradation of atrazine, atraton, ametryn and 2‐hydroxyatrazine by 254 nm light in aqueous solution

On the Low‐Lying Excited States of sym‐Triazine‐Based Herbicides

A novel one-dimensional coordination polymer of cadmium(II)/triazine extending by di-chloro and di-iodo bridges

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