Effects of hydrogen bond formation on vibrations of pyridine, pyrazine, pyrimidine, and pyridazine

Takahashi, Hiroaki; Mamola, Karl C.; Plyler, Earle K.

doi:10.1016/0022-2852(66)90139-1

Cited by 129 publications

(50 citation statements)

References 6 publications

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“…The only difference is the shift to 1586 cm -1 of the 1562-cm -1 band, due to a skeletal vibration of the pyrimidine ring (Lafaix and Lebas, 1970;Takahashi et al, 1966).…”

Section: Fenarimot-clay Complexes At Room Temperaturementioning

confidence: 96%

“…A shift to higher frequencies is a result of the skeletal vibrations of the pyrimidine in a protic solvent (Takahashi et al, 1966). It is, therefore, reasonable that Fenarimol was adsorbed by van der Waals forces and hydrogen bonding between the nitrogen (or the nitrogens) of the pyrimidine ring and the H of the solvation water of the cations.…”

Section: Fenarimot-clay Complexes At Room Temperaturementioning

confidence: 98%

See 1 more Smart Citation

Adsorption and Degradation of Fenarimol on Montmorillonite

Fusi

Ristori

Cecconi

et al. 1983

Clays and clay miner.

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The importance of the non-biochemical reactions in decomposing organic molecules adsorbed on clay surfaces has been emphasized in recent years (Mortland, 1970;Theng, 1974;Crosby, 1976). The nature of the interlayer exchangeable cation is one of the most important factors in the adsorption and transformation of the organic molecules on the clay surface. The higher the charge, the greater is the polarizing effect of the cation on coordinated water molecules which promotes their dissociation and leads to an increase in surface acidity. Moreover, on heating, as the water content decreases, polarization forces become more concentrated on the fewer remaining water molecules causing an increase in hydrolysis and in their proton donating abilities (Farmer and Mortland, 1%6;Mortland and Raman, 1968).The formation of carbonium ions has been demonstrated when triphenylcarbinol is adsorbed on montmorillonite surface. These ions result from the acidity present in the interlayers of the montmorillonite (Fripiat et al., 1964;Helsen, 1970;Helsen et al., 1975). Once adsorbed, this compound transforms into its respective carbonium ions (Ph3-C +) by heating at 100~ as a consequence of the reaction with proton from the solvation water of the exchange cations. Rehydration results in the formation of the triphenylcarbinol.The transformation of the fungicide Fenarimol adsorbed on montmorillonite saturated with different cations was investigated to ascertain whether the substitution of a pyrimidine for a benzene ring affects the nature of the reaction products. EXPERIMENTAL MaterialsHomoionic montmorillonites were prepared from <2-tzm equivalent spherical diameter fraction of a bentonite from Upton, Wyoming, by treatment with I N solutions ofAICl3, CaCIz, BaCI~, MgCI2, CuClz, KCI, and NaCI. The excess salt was eliminated by repeated washings until a test for C1-was negative.The Fenarimol [c~-(2-chlorophenyl)-t~-(4-chlorophenyl)-5-pyrimidinemethanol] was supplied by Elanco (Italy). The melting point of the pure compound (99.8%) was I 18 ~ I 19~ Infrared (IR) analysisThe IR spectrum of the Fenarimol was recorded in a KBr disk. The adsorption of the product on the clay surface was achieved by immersing self-supporting films of the clay in a saturated solution of Fenarimol in CC14. These films were washed with CC14 and air dried. IR spectra of the Fenarimolclay systems were recorded at room temperature on a Model 283B Perkin-Elmer spectrophotometer from: (1) the original sample, (2) the sample after heating at 100~ for 8 hr, (3) sample (2) after equilibration at I00% RH for 5 hr, (4) sample (3) after heating at 100~ for 30 hr, and (5) sample (4) after equilibration at 100% RH for 5 hr. Ultraviolet (UV) analysisUltraviolet spectra of the films of the Fenarimol-clay complexes were recorded on a Model DB-GT Beckman spectrophotometer by placing a pure clay film in the reference beam and wetting the sample with Nujol to avoid scattering. Thin-layer chromatographyFixed amounts of the Fenarimol-clay complexes (original, heated, and humidified) we...

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“…The only difference is the shift to 1586 cm -1 of the 1562-cm -1 band, due to a skeletal vibration of the pyrimidine ring (Lafaix and Lebas, 1970;Takahashi et al, 1966).…”

Section: Fenarimot-clay Complexes At Room Temperaturementioning

confidence: 96%

Section: Fenarimot-clay Complexes At Room Temperaturementioning

confidence: 98%

Adsorption and Degradation of Fenarimol on Montmorillonite

Fusi

Ristori

Cecconi

et al. 1983

Clays and clay miner.

View full text Add to dashboard Cite

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“…In aqueous pyridine solution, the formation of HB between the N site of pyridine and the H site of water is proposed by the vibrational spectroscopy: IR [13] and Raman [14,15]. The formation of HB networks is supported by DFT [14,164,165] and Monte Carlo simulations [166].…”

Section: Pyridine Solutionmentioning

confidence: 98%

“…For example, the OH stretching mode is effectively observed in Raman spectroscopy [10][11][12] to reveal the hydration structure of the anion to the hydrogen of water in aqueous salt solutions. In aqueous pyridine solutions, the HB interaction between N atoms in pyridine and water molecules is revealed by IR [13] and Raman spectroscopy [14,15]; in aqueous acetonitrile solutions, the HB interaction is revealed by the C N and OH stretching modes in IR spectroscopy [9,16,17]. In aqueous methanol solutions, the local structures around methanol molecules at different concentrations are revealed by the C O stretching modes in Raman spectroscopy [18].…”

Section: Introductionmentioning

confidence: 97%

Development and application of in situ/operando soft X-ray transmission cells to aqueous solutions and catalytic and electrochemical reactions

Nagasaka

Yuzawa

Kosugi

2015

Journal of Electron Spectroscopy and Related Phenomena

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“…In all previous experimental studies carried out on pyridine solvated in water 35 and in the gas phase, 36 only the global energy minimum structure was considered. Another study of the heterodimer in chloroform solution also found only the NH conformer.…”

Section: Dependency Of the Bands On Applying A DC Electric Fieldmentioning

confidence: 99%

IR spectroscopy of pyridine–water structures in helium nanodroplets

Nieto

Letzner

Endres

et al. 2014

Phys. Chem. Chem. Phys.

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We present the results of an IR spectroscopic study of pyridine-water heterodimer formation in helium nanodroplets. The experiments were carried out in the frequency range of the pyridine C-H stretch region (3055-3100 cm À1 ) and upon water deuteration in the D-O stretch region (2740-2800 cm À1 ). In order to come to an unambiguous assignment we have determined the angle between the permanent dipole and the vibrational transition moment of the aggregates. The experiments have been accompanied by theoretical simulations which yielded two minimum structures with a 16.28 kJ mol À1 energy difference.The experimentally observed bands were assigned to two structures with different H-bonds: an NÁ Á ÁH bond and a bifurcated OÁ Á ÁH-C bond.

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Effects of hydrogen bond formation on vibrations of pyridine, pyrazine, pyrimidine, and pyridazine

Cited by 129 publications

References 6 publications

Adsorption and Degradation of Fenarimol on Montmorillonite

Adsorption and Degradation of Fenarimol on Montmorillonite

Development and application of in situ/operando soft X-ray transmission cells to aqueous solutions and catalytic and electrochemical reactions

IR spectroscopy of pyridine–water structures in helium nanodroplets

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