Infrared absorption spectra of 2-(hydroxyimino)propanohydroxamic and oxalodihydroxamic acids isolated in argon matrices

Kaczor, Agnieszka; Szczepański, Jan; Vala, Martin; Kozłowski, Henryk; Proniewicz, Leonard M.

doi:10.1039/b302498a

Cited by 14 publications

(9 citation statements)

References 41 publications

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“…Moreover, stretching vibrations of CC (1508 cm –1 ), pyridinic CN (1590 cm –1 ), and C–N = (1450 cm –1 ) groups are observed for these samples, indicating the formation of polyaromatic structures of CDs. , The existence of stretching vibrations of O–H (∼3400 cm –1 ), CO (1620 cm –1 ), and C–N (1427 cm –1 ) and bending of NH 2 (1591 cm –1 , see the magnified view of FT-IR spectra shown in Figure S4b, Supporting Information) in both of the CDs attributed the most likely presence of hydroxamic (−CONHOH) and amine (−NH 2 ) functional groups. In particular, the band that appeared at 1427 cm –1 was the mixed bending vibrations of N–C–H and N–OH groups, corroborating the characteristics of hydroxamic acids . Furthermore, the C–C stretching modes (coupled to N–H bends) were also found at 1217 and 1189 cm –1 , indicating successful functionalization with hydroxamic acids .…”

Section: Resultssupporting

confidence: 57%

“…39 Furthermore, the C−C stretching modes (coupled to N−H bends) were also found at 1217 and 1189 cm −1 , indicating successful functionalization with hydroxamic acids. 39 A small peak at 1030 cm −1 assigned for N−O stretching vibration was also observed. 40 Along with these peaks, the presence of hydroxamic acid functionalities (−CONH−) was believed to be present in these CDs as the observed CO band (1620 cm −1 ) in these CDs has appeared at comparatively lower wavenumber than the normal carbonyl in amides (1680−1630 cm −1 ).…”

Section: Resultsmentioning

confidence: 98%

“…In particular, the band that appeared at 1427 cm −1 was the mixed bending vibrations of N−C−H and N−OH groups, corroborating the characteristics of hydroxamic acids. 39 Furthermore, the C−C stretching modes (coupled to N−H bends) were also found at 1217 and 1189 cm −1 , indicating successful functionalization with hydroxamic acids. 39 A small peak at 1030 cm −1 assigned for N−O stretching vibration was also observed.…”

Section: Resultsmentioning

confidence: 98%

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Carbon Dots from a Single Source Exhibiting Tunable Luminescent Colors through the Modification of Surface Functional Groups in ORMOSIL Films

Bhattacharya

Mishra

2017

J. Phys. Chem. C

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A simple strategy to fabricate carbon dots (CDs) incorporated organically modified silica (ORMOSIL) films exhibiting tunable tricolor emission has been accomplished. First, the green-emitting CDs with excitation-independent nature and high quantum yield were prepared from o-phenylenediamine in ethanol by solvothermal method. These CDs after purification were dispersed in ORMOSIL sol, and their photoluminescence wavelengths were tuned to three intense luminescent colors (orange, yellow, and green) by adjusting the pH of the sol. It was observed that with pH tuning the functional groups residing on surfacepassivated CDs are undergoing chemical modifications, and accordingly the PL emission of CDs in ORMOSIL sol systematically changes to orange, yellow, and green emissions, respectively. Interestingly, the structure of such surface-modified CDs can be well-preserved in the ORMOSIL film-matrix with substantial concentration to obtain the above tricolor luminescent films on glass. A systematic X-ray photoelectron spectroscopy study revealed that the blue shifting in triluminous films (from 560 to 510 nm) with pH increment was originated due to the deprotonation of the surface groups (−CONH− → −CO(N − )−; −NH 3 + → −NH 2 ) associated with the CDs. The plausible mechanism behind the rationalization of pH-triggered engineering of surface-passivated CD-ORMOSIL sols and their confinement in films has been explored.

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Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 98%

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Carbon Dots from a Single Source Exhibiting Tunable Luminescent Colors through the Modification of Surface Functional Groups in ORMOSIL Films

Bhattacharya

Mishra

2017

J. Phys. Chem. C

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“…The former links the carbonyl oxygen with the proton of the hydroxamic OH group and is also found in the most stable structures of oxalodihydroxamic acid and 2-(hydroxy)iminopropanohydroxamic acid. 48 The carbonyl oxygen atom is also involved in a stronger H-bond with the proton of the phenolic group. This is possible due to the presence of the phenolic group ortho to the hydroxamic moiety.…”

Section: Discussionmentioning

confidence: 99%

Matrix-isolation and computational study of salicylhydroxamic acid and its photochemical degradation

Kaczor

Szczepański

Vala

et al. 2005

Phys. Chem. Chem. Phys.

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The IR absorption spectrum of salicylhydroxamic acid (sha) isolated in an argon matrix at 12-21 K has been recorded. Calculations of all the possible entgegen and zusammen keto conformers of sha have been performed at the B3LYP/6-311++G(d,p) level of theory. The computed energies, optimized structures, and relative abundances show that sha exists in the matrix as the z,z,z,z-conformer [relative to the C-O(-H), C-C(-N), C-N and N-O bonds, respectively] and is stabilized by two intramolecular H-bonds. Photofragmentation of the compound in matrix and methanol-water solution has been obtained by irradiation with visible and ultraviolet light. o-Hydroxyphenylisocyanate is the main photolysis product in an argon matrix, while salicylamide is the primary photolysis product in methanol-water solution.

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“…384 For the first time IR spectra of 2-(hydroxyiminopropanohydroxamic acid and oxalodihydroxamic acid in Ar matrices at 15-18 K have been recorded. 385 Only the most stable conformers were seen experimentally. These are keto forms with E and Z arrangements around the C-C and C-N hydroxamic bonds, respectively.…”

Section: Biological Molecules Generalmentioning

confidence: 99%

Chemistry in low-temperature matrices

Almond

Goldberg

2007

Annu. Rep. Prog. Chem., Sect. C: Phys. Chem.

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the Progress of Chemistry, Section C. The report is divided into sections: weak adducts and conformational isomers; reactions of atoms; high-temperature molecules; photochemistry; biological molecules; astrochemistry. The last two sections reflect the fact that matrix isolation now extends into areas outside the traditional mainstream disciplines of chemistry. There are a number of areas where substantial progress has been made during the period of this report. First, the routine use of laser-ablation to generate atoms and to initiate atomic reactions in matrices has increased the scope of matrix isolation to synthesise many new molecular species in inorganic chemistry. Laser-ablation allows ground state atoms to be more easily studied than is the case when atoms are produced by thermal methods. Moreover, this procedure allows atoms to be generated from materials where thermal production is difficult. Secondly, the manufacture of more efficient closed-cycle helium refrigerators allows hydrogen matrices to be deposited readily. A significant body of work therefore has focussed upon metal hydrides, dihydrogen complexes and other hydrogen species in matrices. Underpinning all of this experimental work are theoretical calculations, without which the correct identification of most matrix isolation molecules would remain dangerously ambiguous. Infrared spectroscopy remains-as it has for the past 50 years-the workhorse of matrix isolation studies. It does seem that this situation will not change-it is impossible to conceive of another spectroscopic method that combines the necessary sensitivity to study molecules at very low dilution with the structural information required to make a reasonably certain identification.

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Infrared absorption spectra of 2-(hydroxyimino)propanohydroxamic and oxalodihydroxamic acids isolated in argon matrices

Cited by 14 publications

References 41 publications

Carbon Dots from a Single Source Exhibiting Tunable Luminescent Colors through the Modification of Surface Functional Groups in ORMOSIL Films

Carbon Dots from a Single Source Exhibiting Tunable Luminescent Colors through the Modification of Surface Functional Groups in ORMOSIL Films

Matrix-isolation and computational study of salicylhydroxamic acid and its photochemical degradation

Chemistry in low-temperature matrices

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