An infrared spectroscopic study of hydrogen bonding in thiols

Yablonskii, O. P.; Rodionova, N. M.; Lapuka, L. F.

doi:10.1007/bf00604073

Cited by 6 publications

(7 citation statements)

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“…Stretching vibrations of the thiol group S-H are observed within the range 2500 to 2600 cm À1 (Baranowska et al, 2012;Biswal et al, 2010;Kieninger & Ventura, 2011;Dołęga et al, 2012;Yablonskii et al, 1973;Rozenberg et al, 1999;Becker et al, 1982;Wojnowski & Herman, 1976;Mielcarek & Dołę ga, 2016). We observe this band for TDST at 2556 cm À1 (Fig.…”

Section: Experimental and Calculated Vibrational Spectrasupporting

confidence: 57%

Variable-temperature X-ray diffraction study of structural parameters of NH---S hydrogen bonds in triethylammonium and pyridinium silanethiolates

Mielcarek

Daszkiewicz

Kazimierczuk

et al. 2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Two hydrogen-bonded, well defined compounds were synthesized from tris(2,6-diisopropyl)phenoxysilanethiol (TDST) and triethylamine (TDST-TEA) or pyridine (TDST-py). The crystalline compounds were characterized in the solid state by variable-temperature X-ray diffraction measurements and ATR FT-IR spectroscopy. The toluene solutions of TDST-TEA and TDST-py were studied by NMR spectroscopy. The total hydrogen-bond energies and FT-IR spectra were calculated with the use of BLYP-D/TZP and B3LYP/6-31G(d,p)/GD3BJ methods. Thermochemical parameters and potential energy scans were calculated at the B3LYP/6-31G(d,p)/GD3BJ level. All results point to the higher energy of bonding in TDST-TEA both in the solid state and in solution. At the same time the potential energy scan reveals a very broad double-well hydrogen bond in TDST-py, indicating good stabilization of the system for a wide range of D-H...A distances.

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Section: Experimental and Calculated Vibrational Spectrasupporting

confidence: 57%

Variable-temperature X-ray diffraction study of structural parameters of NH---S hydrogen bonds in triethylammonium and pyridinium silanethiolates

Mielcarek

Daszkiewicz

Kazimierczuk

et al. 2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…The IR spectrum of Mt–Fe(III)Phen semisat exposed to SC7 (or SC6OH) shows strong signals attributable to the CH stretching of the alkyl chain of heptanethiol (or 6-mercapto-1-hexanol) interacting with Mt–Fe(III)Phen (see Figure S6). ,, In both cases, no band due to the SH stretching vibration is observed. , …”

Section: Resultsmentioning

confidence: 86%

“…The band at 2859 cm –1 can be assigned to the symmetric stretching vibration of CH 2 , whereas those at 2953 and 2926 cm –1 to the antisymmetric stretching vibration of CH 2 and CH 3 groups, respectively. − The CS stretching vibration gives rise to a very weak absorption in the infrared spectrum, and cannot be observed in our conditions. No band associated with the SH stretching vibration (sharp and weak signal at 2550–2600 cm –1 ) is observed. , The exposure of Mt–Fe(III)Phen sat to SC6OH (Figure ), SC11OH, SC5COOH, and SC10COOH (see Figure S5) does not lead to any change in the IR spectrum.…”

Section: Resultsmentioning

confidence: 92%

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Effective and Selective Trapping of Volatile Organic Sulfur Derivatives by Montmorillonite Intercalated with a μ-oxo Fe(III)–Phenanthroline Complex

Bernini

Castellini

Malferrari

et al. 2016

ACS Appl. Mater. Interfaces

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The μ-oxo Fe(III)-phenanthroline complex [(OH)(Phen)FeOFe(Phen) (OH)] intercalated in montmorillonite provides a stable hybrid material. In this study, the ability and efficiency of this material to immobilize thiols in gas phase, acting as a trap at the solid-gas interface, were investigated. Aliphatic thiols containing both hydrophilic and hydrophobic end groups were chosen to test the selectivity of this gas trap. DR-UV-vis, IR, elemental analysis, thermal analysis and evolved gas mass spectrometry, X-ray powder diffraction, and X-ray absorption spectroscopy techniques were employed to characterize the hybrid material before and after thiol exposure and to provide information on the entrapping process. Thiol immobilization is very large, up to 21% w/w for heptanethiol. In addition, evidence was obtained that immobilization occurs through the formation of a covalent bond between the iron of the complex and the sulfur of the thiol. This provides an immobilization process characterized by a higher stability with respect to the methods based on physi-adsorption. Thiol immobilization resulted thermally reversible at least for 20 adsorption/desorption cycles. Unlike standard desulfurization processes like hydrotreating and catalytic oxidation which work at high temperatures and pressures, the present system is able to efficiently trap thiols at room temperature and pressure, thus saving energy. Furthermore, we found that the selectivity of thiol immobilization can be tuned acting on the amount of complex intercalated in montmorillonite. In particular, montmorillonite semisaturated with the complex captures both hydrophobic and hydrophilic thiols, while the saturated montmorillonite shows a strong selectivity toward the hydrophobic molecules.

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“…According to Yablonskii et al, 21 -A# = 0.1-0.4 kcal mole" 1 for the SH...S hydrogen bonds and -LH = 0.5-0.8 kcal mole" 1 for the SH...O bonds in mercaptoethers. Hu and Miller 16 determined the SH...S bond strength in the self-associated mercaptan species from the temperature variation of Tgjj.…”

Section: Introductionmentioning

confidence: 99%