212. Structure of benzene. Part II. Direct introduction of deuterium into benzene and the physical properties of hexadeuterobenzene

Ingold, C. K.; Raisin, C. G.; Wilson, Christopher L.; Bailey, C. R.; Topley, B.

doi:10.1039/jr9360000915

Cited by 54 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a result, many volatile organic compounds, such as aliphatic and cyclic hydrocarbons, show inverse isotope effects for elements such as hydrogen and carbon; that is, the liquid phase becomes more depleted in the heavier isotopes during volatilization. This inverse effect was recognized first for hydrogen isotopes in compounds such as acetic acid and benzene. , Approaches to explain and calculate these inverse effects were presented by, for example, Baertschi et al, Bigeleisen et al, and Wolfsberg. ,, According to classic isotope theory, van der Waals interactions induce weaker binding energies for molecules containing the heavier isotopes, which leads to a higher vapor pressure for the heavier isotopologues. It was suggested that during condensation, the intramolecular vibrational frequencies of bonds that involve elements such as H and C shift toward longer wavelengths.…”

mentioning

confidence: 99%

“…This inverse effect was recognized first for hydrogen isotopes in compounds such as acetic acid and benzene. 5,6 Approaches to explain and calculate these inverse effects were presented by, for example, Baertschi et al, Bigeleisen et al,and Wolfsberg. 4,7,8 According to classic isotope theory, van der Waals interactions induce weaker binding energies for molecules containing the heavier isotopes, which leads to a higher vapor pressure for the heavier isotopologues.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Vapor Pressure Isotope Effects in Halogenated Organic Compounds and Alcohols Dissolved in Water

2016

View full text Add to dashboard Cite

Volatilization causes changes in the isotopic composition of organic compounds as a result of different vapor pressures of molecules containing heavy and light isotopes. Both normal and inverse vapor pressure isotope effects (VPIE) have been observed, depending on molecular interactions in the liquid phase and the investigated element. Previous studies have focused mostly on pure compound volatilization or on compounds dissolved in organic liquids. Environmentally relevant scenarios, such as isotope fractionation during volatilization of organics from open water surfaces, have largely been neglected. In the current study, open-system volatilization experiments (focusing thereby on kinetic/-nonequilibrium effects) were carried out at ambient temperatures for trichloromethane, trichloroethene, trichlorofluoromethane, trichlorotrifluoroethane, methanol, and ethanol dissolved in water and, if not previously reported in the literature for these compounds, for volatilization from pure liquids. Stable carbon isotopic signatures were measured using continuous flow isotope ratio mass spectrometry. The results demonstrate that volatilization of the four halogenated compounds from water does not cause a measurable change in the carbon isotopic composition, whereas for pure-phase evaporation, significant inverse isotope effects are consistently observed (+0.3 ‰< ε < + 1.7 ‰). In contrast, methanol and ethanol showed normal isotope effects for evaporation of pure organic liquids (-3.9 ‰ and -1.9 ‰) and for volatilization of compounds dissolved in water (-4.4 ‰ and -2.9 ‰), respectively. This absence of measurable carbon isotope fractionation considerably facilitates the application of isotopic techniques for extraction of field samples and preconcentration of organohalogens-known to be important pollutants in groundwater and in the atmosphere.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Vapor Pressure Isotope Effects in Halogenated Organic Compounds and Alcohols Dissolved in Water

2016

View full text Add to dashboard Cite

show abstract

“…The coordinated benzene resonances appear at z 4.27 and 4.20, respectively, and there is no indication of either H-D exchange or sulfonation after prolonged heating at 80-100". Free benzene in 51 mol% D2S04 readily undergoes H-D exchange at room temperature, and undergoes sulfonation at higher temperatures (25).…”

Section: Reactions Of the Coordinated Benzenementioning

confidence: 99%

Benzene Complexes of Ruthenium(II)

Zelonka¹,

1972

View full text Add to dashboard Cite

show abstract

“…The polarizability of t/s-phenol and deuterated molecules in general is slightly less than for their protium analogs(Ingold et al, 1936; De Bruyne and Smyth, 1935); and thus, they would interact less strongly with nonpolar groups in the protein molecule. This would be a small effect, however.…”

mentioning

confidence: 99%