Conformational properties and photochemistry of new allyl tetrazoles: Matrix isolation FTIR and computational approach

Pagacz-Kostrzewa, Magdalena; Mucha, Małgorzata; Weselski, Marek; Wierzejewska, Maria

doi:10.1016/j.jphotochem.2012.10.023

Cited by 19 publications

(12 citation statements)

References 32 publications

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“…The tetrazolic NH stretching appeared at the frequencies of 2471-3195 cm −1 . 35 Compound 2 can also convert to 3 simultaneously in one step and without the need for separation of 8 (formation of tetrazole followed by deprotection reaction). The IR spectrum of 3 showed a peak at the frequency of 2470 to 3134 cm −1 for the tetrazolic NH group and a peak at the frequency of 3383 cm −1 corresponded to ammonium salt moiety, while some peaks of this group overlapped with the peaks of the tetrazolic NH group.…”

Section: Chemistrymentioning

confidence: 99%

New tetrazolic azo dyes linked to (thio)barbiturate and electron-rich aromatics as potential antimicrobial agents

Pesyan

Soleimani²,

Jazani³

2015

Turk J Chem

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A series of new tetrazolic azo dyes based on (thio)barbiturate and electron-rich aromatics were synthesized in excellent yield. The electron-donor and tetrazole ring moieties were linked by a p -phenylazo bridge and the structural characterizations were achieved by FT IR, 1 H and 13 C NMR, and UV-visible spectrometry. The antibacterial activity of the synthesized compounds was tested against gram-positive and gram-negative bacterial strains, namely Acinetobacter calcoaceticus (ATCC23055), Escherichia coli (ATCC2592), Pseudomonas aeruginosa (ATCC27853), and Staphylococcus aureus (ATCC25923). As a result, potential antimicrobial effects were seen for some of the synthesized compounds.

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Section: Chemistrymentioning

confidence: 99%

New tetrazolic azo dyes linked to (thio)barbiturate and electron-rich aromatics as potential antimicrobial agents

Pesyan

Soleimani²,

Jazani³

2015

Turk J Chem

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“…5; top panels), which is a very characteristic spectroscopic signature of carbodiimides (N=C=N antisymmetric stretching). [41][42][43][44] In the studied low-frequency region between 1650 and ϳ600 cm −1 , the predicted spectrum for the carbodiimide fits also rather well the experimental spectrum of the photoproduct (see Table 3 for proposed assignments), with two notable exceptions: the calculations predict the C-O and N-O stretching modes of the molecule to appear as relatively intense bands at approximately 1206 and 886 cm −1 , respectively, while no prominent bands are observed at these frequencies in the experimental spectrum. However, a broad band spreading from 893 to 905 cm −1 is indeed observed in the experimental spectrum, which can be correlated with the N-O vibration of the carbodiimide, while in the 1215-1265 cm −1 range, the experimental spectrum presents a series of at least five low-intensity bands that one can assign to the C-O vibration.…”

Section: Uv-laser-induced Photochemistry Of Matrix-isolated 5pptmentioning

confidence: 99%

Structure, vibrational spectroscopy, and photochemistry of 5-phenoxy-1-phenyltetrazole in argon and nitrogen cryomatrices

et al. 2015

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The molecular structure, infrared spectra, and photochemistry of 5-phenoxy-1-phenyltetrazole (5PPT) isolated in argon and N 2 cryogenic matrices were investigated by infrared spectroscopy and theoretical calculations (DFT(B3LYP)/6-311++G(d,p)). Calculations yield two dissimilar minima on the potential energy surface of the molecule, both being eightfold degenerate by symmetry and belonging to the C 1 symmetry point group. Extensive analysis of the potential energy landscape of the molecule was performed. Upon consideration of the zero-point vibrational correction to the energy, the calculations predict that the higher energy minimum shall relax barrierlessly to the lower energy form, leading to conclude that the compound exists in a single conformer in the gas phase. Accordingly, a single conformer was observed and fully characterized spectroscopically upon isolation of the monomer of the compound in argon and nitrogen cryomatrices. UV-laser irradiation ( = 250 nm) of matrixisolated 5PPT leads to photocleavage of the tetrazole ring, with release of N 2 and formation of the corresponding carbodiimide.Résumé : La structure moléculaire, les spectres infrarouges et la photochimie de 5-phénoxy-1-phényltétrazole (5PPT) isolé dans des matrices cryogéniques de l'argon et de N 2 ont été étudiés par spectroscopie d'infrarouges et calculs théoriques (DFT(B3LYP)/ 6-311++G(d,p)). Les calculs donnent deux minima différents sur la surface d'énergie potentielle de la molécule, les deux étant de huit fois dégénéré par symétrie et appartenant au groupe de points de symétrie C 1 . Une analyse approfondie du paysage d'énergie potentielle de la molécule a été effectuée. Après examen des corrections du point zéro de vibration à l'énergie, les calculs prédisent que le minimum d'énergie plus élevée doit détendre sans barrière à la forme d'énergie plus faible, ce qui permet de conclure que le composé existe comme un seul conformère dans la phase gazeuse. En effet, un seul conformère a été observé, et caractérisé entièrement par spectroscopie, après l'isolement du monomère du composé dans des cryomatrices de l'argon et d'azote. Irradiation de 5PPT isolé en cryomatrice de l'argon avec laser UV ( = 250 nm) conduit à photoclivage de l'heterocicle tetrazole avec sortie de N 2 et production de la carbodiimide correspondante.

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“…[16][17][18][22][23][24][25][26][27][28] Substituents were found to have a significant effect on the structural characteristics of nitrile imines. [16][17][18][22][23][24][25][26][27][28] Substituents were found to have a significant effect on the structural characteristics of nitrile imines.…”

Section: Introductionmentioning

confidence: 99%

The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C‐Amino Nitrile Imine

et al. 2015

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C‐Amino nitrile imine has been generated as primary photoproduct (λ = 220 nm) of 5‐amino‐2H‐tetrazole isolated in an argon matrix at 15 K. Subsequent photochemical experiments (λ = 330 nm) demonstrated that C‐amino nitrile imine isomerizes to the corresponding three‐membered‐ring 1H‐diazirine and decomposes to methylenimine. The experimentally observed νas(CNN) absorption at 1998 cm–1 and a carbenic resonance structure contribution of around 20 %, predicted by natural resonance theory calculations, demonstrate that the protoproduced C‐amino nitrile imine has significant carbenic character. These results pave the way to the discovery of carbenic nitrile imines.

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Conformational properties and photochemistry of new allyl tetrazoles: Matrix isolation FTIR and computational approach

Cited by 19 publications

References 32 publications

New tetrazolic azo dyes linked to (thio)barbiturate and electron-rich aromatics as potential antimicrobial agents

New tetrazolic azo dyes linked to (thio)barbiturate and electron-rich aromatics as potential antimicrobial agents

Structure, vibrational spectroscopy, and photochemistry of 5-phenoxy-1-phenyltetrazole in argon and nitrogen cryomatrices

The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C‐Amino Nitrile Imine

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