Enthalpies of interaction of aromatic solutes with organic solvents

1985 ◽  
Vol 63 (9) ◽  
pp. 2529-2534 ◽  
Author(s):  
W. Kirk Stephenson ◽  
Richard Fuchs
Keyword(s):  
Organic Solvents ◽  
Butyl Alcohol ◽  
Model Compounds ◽  
Butyl Ether ◽  
Enthalpies Of Transfer ◽  
Benzene Toluene ◽  
Polar Interactions ◽  
S Model ◽  
Heats Of Vaporization ◽  
Butyl Methyl Ether

Heats of solution of several aromatic solutes (benzene, toluene, mesitylene, nitrobenzene, α,α,α-trifluorotoluene, anisole) and model compounds (n-butyl methyl ether, cyclohexane) in 17 organic solvents (n-heptane, cyclohexane, carbon tetrachloride, 1,2-dichloroethane, α,α,α-trifluorotoluene, triethylamine, butyl ether, ethyl acetate, dimethylformamide, dimethyl sulfoxide, benzene, toluene, mesitylene, t-butyl alcohol, 1-octanol, methanol, 2,2,2-trifluoroethanol) have been combined with solute heats of vaporization to give enthalpies of transfer from vapor to solvent (ΔH(v → S)). Differences between solute and model values (ΔΔH(v → S) = ΔH(v → S) (aromatic solute)–ΔH(v → S) (model) were used to evaluate aromatic solute–solvent polar interactions. Correlations of ΔΔH(v → S) with solvent dipolarity–polarizability (Taft–Kamlet π* parameter) have been determined.

Enthalpies of interaction of nitrogen base solutes with organic solvents

1985 ◽  
Vol 63 (9) ◽  
pp. 2540-2544 ◽  
Author(s):  
W. Kirk Stephenson ◽  
Richard Fuchs
Keyword(s):  
Hydrogen Bond ◽  
Organic Solvents ◽  
Butyl Alcohol ◽  
Hydrogen Bond Donor ◽  
Butyl Ether ◽  
Hydrogen Bond Acceptor ◽  
Nitrogen Base ◽  
Benzene Toluene ◽  
Polar Interactions ◽  
S Model

Heats of solution of triethylamine, aniline, pyridine, and model compounds (3-ethylpentane, benzene) in 17 organic solvents (n-heptane, cyclohexane, carbon tetrachloride, 1,2-dichloroethane, α,α,α-trifluorotoluene, triethylamine, butyl ether, ethyl acetate, dimethylformamide, dimethyl sulfoxide, benzene, toluene, mesitylene, t-butyl alcohol, 1-octanol, methanol, 2,2,2-trifluoroethanol) have been combined with solute heats of vaporization to give enthalpies of transfer from vapor to solvent (ΔH(v → s)). Differences between solute and model values (ΔΔH(v → s) = ΔH(v → s) (solute) – ΔH(v → s) (model)) were used to evaluate nitrogen base solute–solvent polar interactions. Correlations of ΔΔH(v → s) with Taft–Kamlet solvatochromic parameters (π*, α, β) have been determined.Aniline was found to be a better hydrogen bond donor acid than hydrogen bond acceptor base. Nevertheless, alcohols donate H-bonds to aniline. Triethylamine and pyridine are stronger HBA bases than aniline. The π* (dipolarity–polarizability) parameter of aniline (as a solute) is calculated to be 1.10.

Enthalpies of interaction of hydroxylic solutes with organic solvents

1985 ◽  
Vol 63 (9) ◽  
pp. 2535-2539 ◽  
Author(s):  
W. Kirk Stephenson ◽  
Richard Fuchs
Keyword(s):  
Organic Solvents ◽  
Methyl Ether ◽  
Butyl Alcohol ◽  
Amyl Alcohol ◽  
Solvatochromic Parameters ◽  
Model Compounds ◽  
Butyl Ether ◽  
Donor Solvent ◽  
Benzene Toluene ◽  
Butyl Methyl Ether

Heats of solution of m-cresol, 1-butanol, 1-pentanol, t-amyl alcohol, and model compounds (toluene, ethyl ether, n-butyl methyl ether, t-butyl methyl ether) in 17 organic solvents (n-heptane, cyclohexane, carbon tetrachloride, 1,2-dichloroethane, α,α,α-trifluorotoluene, triethylamine, butyl ether, ethyl acetate, dimethylformamide, dimethyl sulfoxide, benzene, toluene, mesitylene, t-butyl alcohol, 1-octanol, methanol, 2,2,2-trifluoroethanol) have been combined with solute heats of vaporization to give solvation enthalpies (ΔH(v → S)). Dependencies of solute vs. model solvation enthalpy differences on solvent dipolarity–polarizability and hydrogen-bond-accepting basicity were determined via correlations with Taft–Kamlet solvatochromic parameters (π*, β, ξ).m-Cresol is a substantially stronger H-bond donor than 1-butanol, 1-pentanol, and t-amyl alcohol, and H-bonds to acceptor solvents including alcohols. Cresol acts as an H-bond acceptor with the strong H-bond donor solvent trifluoroethanol.

Enthalpies of interaction of ketones with organic solvents

1985 ◽  
Vol 63 (2) ◽  
pp. 336-341 ◽  
Author(s):  
W. Kirk Stephenson ◽  
Richard Fuchs
Keyword(s):  
Organic Solvents ◽  
Bond Formation ◽  
Butyl Alcohol ◽  
Enthalpies Of Solution ◽  
Butyl Ether ◽  
Hydrogen Bond Formation ◽  
Linear Relationships ◽  
Benzene Toluene ◽  
Polar Interactions ◽  
Alcohol Solvents

Enthalpies of solution (ΔHS) of a series of ketones (acetone, 2-butanone, 2-heptanone, 2-nonanone, 5-nonanone, 2,2,4,4-tetramethyl-3-pentanone, cyclohexanone) and alkane model compounds (n-heptane, n-nonane, 2,2,4,4-tetramethylpentane, cyclohexane) have been determined in 17 organic solvents (n-heptane, cyclohexane, CCl4, α,α,α,-trifluorotoluene, 1,2-dichloroethane, triethylamine, butyl ether, ethyl acetate, DMF, DMSO, benzene, toluene, mesitylene, 1-octanol, methanol, t-butyl alcohol, 2,2,2-trifluoroethanol), and combined with heats of vaporization to give enthalpies of transfer from vapor to solvent (ΔH(v → S)). These values have been used to evaluate ketone–solvent polar interactions (ΔΔH(v → S) = ΔH(v → S)(ketone) − ΔH(v → S)(alkane)). The linear relationships between ΔΔH(v → S) and solvent dipolarity-polarizability (Taft-Kamlet π* parameters) are derived. Based on the deviations from these correlations, ketone–CF3CH2OH enthalpies of hydrogen bond formation have been evaluated. The other alcohol solvents show no evidence of exothermic H-bond formation with ketones.

Hydrogen bonding and other polar interactions of 1-, 2-, and 4-octyne with organic solvents

1983 ◽  
Vol 61 (9) ◽  
pp. 2044-2047 ◽  
Author(s):  
John H. Hallman ◽  
W. Kirk Stephenson ◽  
Richard Fuchs
Keyword(s):  
Hydrogen Bond ◽  
Bond Formation ◽  
Butyl Ether ◽  
Hexamethylphosphoric Triamide ◽  
Hydrogen Bond Formation ◽  
Enthalpies Of Transfer ◽  
Induced Dipole ◽  
Base Method ◽  
Polar Interactions ◽  
Heats Of Vaporization

The heats of vaporization of 1-octyne (10.11 ± 0.02 kcal/mol), 2-octyne (10.63 ± 0.03 kcal/mol), and 4-octyne (10.21 ± 0.02 kcal/mol) have been determined. Heats of solution of the liquid octynes and n-octane have been measured in heptane, cyclohexane, 1,2-dichloroethane, n-butyl ether, ethanol, triethylamine, dimethyl sulfoxide, butyrolactone, dimethylformamide, and hexamethylphosphoric triamide. Enthalpies of transfer from vapor to each solvent have been calculated. Enthalpies of hydrogen bond formation, calculated by the pure base method, become more exothermic in the above solvent order. Correlations with the Taft–Kamlet solvent parameters π* and β indicate that other polar interactions (presumably dipole – induced dipole) are appreciably larger for 1-octyne than for 2- and 4-octyne.

scholarly journals Degradation of a Mixture of Hydrocarbons, Gasoline, and Diesel Oil Additives by Rhodococcus aetherivorans and Rhodococcus wratislaviensis

2009 ◽  
Vol 75 (24) ◽  
pp. 7774-7782 ◽  
Author(s):  
Marc Auffret ◽  
Diane Labbé ◽  
Gérald Thouand ◽  
Charles W. Greer ◽  
Françoise Fayolle-Guichard
Keyword(s):  
Detrimental Effect ◽  
Dry Weight ◽  
Diesel Oil ◽  
Butyl Alcohol ◽  
Butyl Ether ◽  
Oil Additives ◽  
Degradation Rates ◽  
Benzene Toluene ◽  
Rhodococcus Wratislaviensis ◽  
Positive Effect

ABSTRACT Two strains, identified as Rhodococcus wratislaviensis IFP 2016 and Rhodococcus aetherivorans IFP 2017, were isolated from a microbial consortium that degraded 15 petroleum compounds or additives when provided in a mixture containing 16 compounds (benzene, toluene, ethylbenzene, m-xylene, p-xylene, o-xylene, octane, hexadecane, 2,2,4-trimethylpentane [isooctane], cyclohexane, cyclohexanol, naphthalene, methyl tert-butyl ether [MTBE], ethyl tert-butyl ether [ETBE], tert-butyl alcohol [TBA], and 2-ethylhexyl nitrate [2-EHN]). The strains had broad degradation capacities toward the compounds, including the more recalcitrant ones, MTBE, ETBE, isooctane, cyclohexane, and 2-EHN. R. wratislaviensis IFP 2016 degraded and mineralized to different extents 11 of the compounds when provided individually, sometimes requiring 2,2,4,4,6,8,8-heptamethylnonane (HMN) as a cosolvent. R. aetherivorans IFP 2017 degraded a reduced spectrum of substrates. The coculture of the two strains degraded completely 13 compounds, isooctane and 2-EHN were partially degraded (30% and 73%, respectively), and only TBA was not degraded. Significant MTBE and ETBE degradation rates, 14.3 and 116.1 μmol of ether degraded h−1 g−1 (dry weight), respectively, were measured for R. aetherivorans IFP 2017. The presence of benzene, toluene, ethylbenzene, and xylenes (BTEXs) had a detrimental effect on ETBE and MTBE biodegradation, whereas octane had a positive effect on the MTBE biodegradation by R. wratislaviensis IFP 2016. BTEXs had either beneficial or detrimental effects on their own degradation by R. wratislaviensis IFP 2016. Potential genes involved in hydrocarbon degradation in the two strains were identified and partially sequenced.

scholarly journals Biodegradation of Methyl tert-Butyl Ether and Other Fuel Oxygenates by a New Strain, Mycobacterium austroafricanum IFP 2012

2002 ◽  
Vol 68 (6) ◽  
pp. 2754-2762 ◽  
Author(s):  
Alan François ◽  
Hugues Mathis ◽  
Davy Godefroy ◽  
Pascal Piveteau ◽  
Françoise Fayolle ◽  
...  
Keyword(s):  
Polyacrylamide Gel Electrophoresis ◽  
Sodium Dodecyl ◽  
Dry Weight ◽  
Butyl Alcohol ◽  
Amyl Alcohol ◽  
Methyl Tert Butyl Ether ◽  
Methylotrophic Bacterium ◽  
Specific Rate ◽  
Butyl Ether ◽  
Mycobacterium Austroafricanum

ABSTRACT A strain that efficiently degraded methyl tert-butyl ether (MTBE) was obtained by initial selection on the recalcitrant compound tert-butyl alcohol (TBA). This strain, a gram-positive methylotrophic bacterium identified as Mycobacterium austroafricanum IFP 2012, was also able to degrade tert-amyl methyl ether and tert-amyl alcohol. Ethyl tert-butyl ether was weakly degraded. tert-Butyl formate and 2-hydroxy isobutyrate (HIBA), two intermediates in the MTBE catabolism pathway, were detected during growth on MTBE. A positive effect of Co2+ during growth of M. austroafricanum IFP 2012 on HIBA was demonstrated. The specific rate of MTBE degradation was 0.6 mmol/h/g (dry weight) of cells, and the biomass yield on MTBE was 0.44 g (dry weight) per g of MTBE. MTBE, TBA, and HIBA degradation activities were induced by MTBE and TBA, and TBA was a good inducer. Involvement of at least one monooxygenase during degradation of MTBE and TBA was shown by (i) the requirement for oxygen, (ii) the production of propylene epoxide from propylene by MTBE- or TBA- grown cells, and (iii) the inhibition of MTBE or TBA degradation and of propylene epoxide production by acetylene. No cytochrome P-450 was detected in MTBE- or TBA-grown cells. Similar protein profiles were obtained after sodium dodecyl sulfate-polyacrylamide gel electrophoresis of crude extracts from MTBE- and TBA-grown cells. Among the polypeptides induced by these substrates, two polypeptides (66 and 27 kDa) exhibited strong similarities with known oxidoreductases.

scholarly journals Nuclear Resonance Vibrational Spectroscopy (NRVS) of Fe–S model compounds, Fe–S proteins, and nitrogenase

2007 ◽  
Vol 170 (1-3) ◽  
pp. 47-54 ◽  
Author(s):  
Stephen P. Cramer ◽  
Yuming Xiao ◽  
Hongxin Wang ◽  
Yisong Guo ◽  
Matt C. Smith
Keyword(s):  
Vibrational Spectroscopy ◽  
Nuclear Resonance ◽  
Model Compounds ◽  
Nuclear Resonance Vibrational Spectroscopy ◽  
S Model ◽  
S Proteins
Sign in / Sign up

Export Citation Format

Share Document