Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

Pagacz-Kostrzewa, Magdalena; Sałdyka, Magdalena; Bil, Andrzej; Gul, W.; Wierzejewska, Maria; Khomenko, Dmytro M.; Doroschuk, Roman O.

doi:10.1021/acs.jpca.8b10762

Cited by 12 publications

(4 citation statements)

References 57 publications

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“…The behavior of this band during photolysis is shown in Figure S8. This intense band is characteristic of structures containing the isocyano, cyano or carbodiimide group [16,[21][22][23][24]. Considering the cleavage of the S1-C2 bond as the mechanism of initial photoproduct formation postulated for the thiazole molecule, similar reaction can be proposed for AMT.…”

Section: Ring-opening Reactions By Cleavage Of the S1-c2 Bondmentioning

confidence: 97%

“…These experiments allowed for interesting photo-transformations to be detected. Literature reports on photochemical rearrangements of thiazole, thiazole derivatives and five-membered ring heterocycles in general [13,16,[19][20][21][22], allowed to propose the photoreaction pathways of 2-amino-4-methylthiazole. All proposed paths of photolysis of AMT are presented in Figure S5 and Figure S6.…”

Section: Photolysismentioning

confidence: 99%

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Structure, Spectra and Photochemistry of 2-Amino-4-Methylthiazole: FTIR Matrix Isolation and Theoretical Studies

et al. 2022

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The structure, tautomerization pathways, vibrational spectra, and photochemistry of 2-amino-4-methylthiazole (AMT) molecule were studied by matrix isolation FTIR spectroscopy and DFT calculations undertaken at the B3LYP/6-311++G(3df,3pd) level of theory. The most stable tautomer with the five-membered ring stabilized by two double C=C and C=N bonds, was detected in argon matrices after deposition. When the AMT/Ar matrices were exposed to 265 nm selective irradiation, three main photoproducts, N-(1-sulfanylprop-1-en-2-yl)carbodiimide (fp1), N-(1-thioxopropan-2-yl)carbodiimide (fp2) and N-(2-methylthiiran-2-yl)carbodiimide (fp3), were photoproduced by a cleavage of the CS–CN bond together with hydrogen atom migration. The minor photoreaction caused by the cleavage of the CS–CC bond and followed by hydrogen migration formed 2-methyl-1H-azirene-1-carbimidothioic acid (fp15). We have also found that cleavage of the CS–CN bond followed by disruption of the N–C bond produced cyanamide (fp11) and the ˙C(CH3)=CH–S˙ biradical that transformed into 2-methylthiirene (fp12) and further photoreactions produced 1-propyne-1-thiole (fp13) or methylthioketene (fp14). Cleavage of the CS–CC bond followed by disruption of the N–C bond produced propyne (fp22) and the ˙S–C(NH2)=N˙ biradical that transformed into 3-aminethiazirene (fp23); further photoreactions produced N-sulfanylcarbodiimide (fp25). As a result of these transformations, several molecular complexes were identified as photoproducts besides new molecules in the AMT photolysis process.

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Section: Ring-opening Reactions By Cleavage Of the S1-c2 Bondmentioning

confidence: 97%

Section: Photolysismentioning

confidence: 99%

Structure, Spectra and Photochemistry of 2-Amino-4-Methylthiazole: FTIR Matrix Isolation and Theoretical Studies

et al. 2022

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“…In addition, it should be noted that the presence of both carboxylic and 1,2,4-triazole groups as parts of one molecule provides interesting theoretical insights into the structural peculiarities of these molecules. This is mainly due to the possibility of 1,2,4-triazole existing in three tautomeric forms (Pagacz-Kostrzewa et al, 2019. Generally, compounds containing a carboxylic function are probably the most important materials for high-throughput synthesis and 1,2,4-triazoles are not an exception.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld-surface analysis of diaquabis(5-methyl-1H-1,2,4-triazole-3-carboxylato)copper(II)

Petrenko,

Vynohradov,

Khomenko

et al. 2024

Acta Cryst E

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The title compound, [Cu(HL)2(H2O)2] or [Cu(C4H4N3O2)2(H2O)2], is a mononuclear octahedral CuII complex based on 5-methyl-1H-1,2,4-triazole-3-carboxylic acid (H2 L). [Cu(HL)2(H2O)2] was synthesized by reaction of H2 L with copper(II) nitrate hexahydrate (2:1 stoichiometric ratio) in water under ambient conditions to produce clear light-blue crystals. The central Cu atom exhibits an N2O4 coordination environment in an elongated octahedral geometry provided by two bidentate HL − anions in the equatorial plane and two water molecules in the axial positions. Hirshfeld surface analysis revealed that the most important contributions to the surface contacts are from H...O/O...H (33.1%), H...H (29.5%) and H...N/N...H (19.3%) interactions.

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“…As shown in Fig. 8c, the N1s peaks of 3-ATAR were deconvoluted into two peaks: imine nitrogen (C = N) in the triazole ring and/or nitrogen atoms of the deprotonated triazole ring (399.42 eV), imino group (N-H) (401.14 eV) (Pagacz-Kostrzewa et al 2019). In acid solution, the C = N and N-H of 3-ATAR were protonated, providing abundant adsorption sites that would interact with ReO 4 − via electrostatic attraction.…”

Section: Xps Analysismentioning

confidence: 99%

Efficient separation and recovery of Re (VII) from Re/U bearing acidic solutions using aminotriazole modified cellulose microsphere adsorbents

Wen

Hua²,

Dong

et al. 2021

Preprint

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In this work, aminotriazole-modified microcrystalline cellulose microspheres (3-ATAR) containing an abundant nitrogen content as promising adsorbent was prepared via a radiation grafting method for the selective recovery ReO4- in the presence of UO22+ in acidic solution. A series of batch and column adsorption experiments including monocomponent and binary systems, were designed for evaluating the adsorption and separation performance of Re (VII) onto 3-ATAR. The 3-ATAR exhibited a good adsorption capacity (max 146.4 mg·g-1) of Re(VII) and a rapid adsorption rate, with equilibrium time of 45 min. In binary solution, the high selectivity coefficients (βRe/M) indicated that 3-ATAR could separate and recover Re(VII) from U(VI) and other metal ions (Cu(II), Cr(III), Ni(II), Zn(II)). In particular, it was found that the adsorption of Re was almost unaffected in U/Re-bearing solutions no matter how much the U(VI) was changed. In the column experiment, when the concentration of U(VI) was 40 times higher than that of Re(VII), 3-ATAR manifested high Re(VII) selectivity over U(VI) from a synthetic uranium ore leachate. This work demonstrated that 3-ATAR could provide an efficient, selectively, sustainable, and industrially feasible way for Re(VII) to be recovered from uranium ore leachate and other prospective sources.

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Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

Cited by 12 publications

References 57 publications

Structure, Spectra and Photochemistry of 2-Amino-4-Methylthiazole: FTIR Matrix Isolation and Theoretical Studies

Structure, Spectra and Photochemistry of 2-Amino-4-Methylthiazole: FTIR Matrix Isolation and Theoretical Studies

Crystal structure and Hirshfeld-surface analysis of diaquabis(5-methyl-1H-1,2,4-triazole-3-carboxylato)copper(II)

Efficient separation and recovery of Re (VII) from Re/U bearing acidic solutions using aminotriazole modified cellulose microsphere adsorbents

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