@article {2460, title = {Hydrophobicity/Hydrophilicity of 1-Butyl-2,3-dimethyl and 1-Ethyl-3-methylimodazolium Ions: Toward Characterization of Room Temperature Ionic Liquids}, journal = {Journal of Physical Chemistry B}, volume = {113}, number = {44}, year = {2009}, note = {ISI Document Delivery No.: 510QMTimes Cited: 2Cited Reference Count: 52Kato, Hitoshi Miki, Kumiko Mukai, Tomohiro Nishikawa, Keiko Koga, Yoshikata}, month = {Nov}, pages = {14754-14760}, type = {Article}, abstract = {We continue to experimentally characterize the constituent ions of room temperature ionic liquids in terms of their interactions with H2O. By using the so-called 1-propanol probing methodology, we experimentally index the relative hydrophobicity/hydrophilicity of a test ion. In this paper, we examine 1-butyl-2,3 dimethylimidazolium (abbreviated as [C(4)C(1)mim](+)) and 1-ethyl-3-methylimidazolium ([C(2)mim](+)). We found that [C(4)C(1)mim](+) dissociates completely in dilute aqueous solution less than 0.006 mol fraction, and hence, its hydrophobicity/hydrophilicity could be determined. The results indicate that [C(4)C(1)mim](+) is highly amphiphilic with much stronger hydrophobicity and hydrophilicity than normal ions. Our earlier similar studies indicated the same conclusion for such typical constituent ions as 1-butyl-3-methylimidazolium ([C(4)mim](+)) PF6-, CF3SO3-, and N(SO2CF3)(2)(-). Hence, we suggest that the constituent ions of room temperature ionic liquids that we have studied so far are all amphiphiles with much stronger hydrophobicity and hydrophilicity than normal ions. We found, furthermore, that the hydrophobicity and hydrophilicity of [C(4)C(1)mim](+) are stronger than those for [C(4)mim](+). A possible reason for higher hydrpohilicity is discussed in terms of strong acidic character of H on the C(2) of the imidazolium ring, which tends to attract the delocalized positive charge toward itself oil forming a hydrogen bond to H2O. On replacing it with CH3 in [C(4)C(1)mim](+), the lack of acidic H enhances the positive charge in the vicinity of N-C-N in the ring that interacts with the surrounding H2O strongly to an induced dipole of O of the H2O. For [C(2)mim](+), we found it does not dissociate completely, even in dilute aqueous solution, and hence, we could not characterize it within the present methodology.}, keywords = {1-BUTYL-3-METHYLIMIDAZOLIUM BROMIDE, AGGREGATION BEHAVIOR, ALKYL CHAIN-LENGTH, APPROACH, AQUEOUS-SOLUTIONS, HOFMEISTER SERIES, MIXING SCHEMES, MOLECULAR-ORGANIZATION, partial molar enthalpy, PHYSICOCHEMICAL PROPERTIES, THERMODYNAMIC}, isbn = {1520-6106}, url = {://000271105600027}, author = {Kato, H. and Miki, K. and Mukai, T. and Nishikawa, K. and Koga,Yoshikata} } @article {7201, title = {AN ENANTIOSPECIFIC ROUTE TO C,D RING SYNTHONS FOR STEROID-SYNTHESIS}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {70}, number = {5}, year = {1992}, note = {ISI Document Delivery No.: JL870Times Cited: 18Cited Reference Count: 68}, month = {May}, pages = {1537-1544}, type = {Article}, abstract = {A simple enantiospecific route to a hydrindenone intermediate for steroid synthesis has been accomplished. The introduction of a wide variety of side-chain units is made possible hy stereoselective alkylation of a bicyclic ester 13 derived from (+)-camphor 4.}, keywords = {APPROACH, asymmetric, CONSTRUCTION, Diels-Alder, ENANTIOSELECTIVE SYNTHESIS, GAMMA-BUTYROLACTONE DERIVATIVES, INHOFFEN-LYTHGOE DIOL, SIDE-CHAIN CONSTRUCTION, STEREOCONTROLLED, STEREOSELECTIVE SYNTHESIS, TANDEM ALKYLATION, TRIPLY CONVERGENT SYNTHESIS, VITAMIN-D METABOLITES}, isbn = {0008-4042}, url = {://A1992JL87000031}, author = {Clase, J. A. and Money, T.} } @article {7036, title = {STEREOSELECTIVITY OF C(3) METHYLATION AND ALDOL CONDENSATION OF CAMPHOR AND DERIVATIVES}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {69}, number = {3}, year = {1991}, note = {ISI Document Delivery No.: FE808Times Cited: 14Cited Reference Count: 38}, month = {Mar}, pages = {558-566}, type = {Article}, abstract = {The stereoselectivity of methylation and aldol condensation of camphor and derivatives is determined by the presence or absence of a C(7) syn-methyl group and (or) C(5) and C(6) endo-hydrogen atoms.}, keywords = {APPROACH, BICYCLO<2.2.1>HEPTANES, C(3)ALDOL, C(3)METHYLATION, CAMPHOR, NUCLEAR MAGNETIC-RESONANCE, ORGANIC-SYNTHESIS, PSEUDOGUAIANOLIDES, STEREOCONTROLLED, VITAMIN-D METABOLITES}, isbn = {0008-4042}, url = {://A1991FE80800029}, author = {Hutchinson, J. H. and Li, D. L. F. and Money, T. and Palme, M. and Agharahimi, M. R. and Albizati, K. F.} } @article {6996, title = {VERATRYL ALCOHOL AS A MEDIATOR IN LIGNIN MODEL-COMPOUND BIODEGRADATION}, journal = {Holzforschung}, volume = {45}, number = {1}, year = {1991}, note = {ISI Document Delivery No.: FC210Times Cited: 7Cited Reference Count: 22}, month = {Feb}, pages = {31-35}, type = {Article}, abstract = {Veratryl alcohol and 1,4-dimethoxybenzene were found to be ineffective mediators for the oxidation of anisyl alcohol by the lignin peroxidase model, iron meso-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin chloride (TDCSPPFeCl). However, veratryl alcohol can mediate the electrochemical oxidation of the polymeric dye Poly B-411. The TDCSPPFeCl catalyzed reactions of lignin model compounds were found to be dependent on pH and the solvent being used. The importance of the mediating role of veratryl alcohol in lignin degradation is discussed.}, keywords = {APPROACH, BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM, BIOMIMETIC, BURDS, C BOND-CLEAVAGE, DEGRADATION, ENZYME, IRON PORPHYRINS, LIGNIN, MECHANISM, MEDIATOR, OXIDATION, PEROXIDASE, PORPHYRIN, SYSTEM, VERATRYL ALCOHOL}, isbn = {0018-3830}, url = {://A1991FC21000006}, author = {Cui, F. T. and Dolphin, D.} }