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Journal articles on the topic 'Trifluoroethanol'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 March 2023

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1

Boston, H. G., V. Sreenivasulu Reddy, P. E. Cassidy, J. W. Fitch, Diane Stoakley, and Anne St Clair. "New Aromatic Diacids Containing the Trifluoromethyl Group and their Polyamides." High Performance Polymers 9, no. 3 (September 1997): 323–32. http://dx.doi.org/10.1088/0954-0083/9/3/010.

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A series of new fluorinated, high-temperature polymers has been prepared from 1, 1, - bis( p-carboxyphenyl)-2, 2, 2-trifluoroethanol (3FOH). This diacid was synthesized by oxidation of 1, 1-di( p-tolyl)-2, 2, 2-trifluoroethanol, which was obtained from p-bromotoluene and ethyl trifluoroacetate. The 3FOH was also reacted with dimethyl sulphate to yield 1-methoxy-1, 1- bis( p-carboxyphenyl)-2, 2, 2-trifluoroethane (3FM), and with SOCl2 to produce 1-chloro-1, 1- bis( p-chloroformylphenyl)-2, 2, 2-trifluoroethane (3FCl). These two diacids, as the acid chlorides, were polymerized with six aromatic and four aliphatic diamines to produce polyamides which had viscosities ranging from 0.32 to 1.52 dl g−1, thermal stabilities up to 518 °C in nitrogen and glass transition temperatures from 165 °C to 337 °C. The dielectric constants of these polyamides ranged from 2.64 to 2.99. The 3FM- and 3FCl-containing polyamides were compared with the 6F (hexafluoroisopropylidene) analogues and found to be somewhat less thermally stable and had equal or lower Tgs.

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2

Schwertfeger, Hartmut. "2,2,2-Trifluoroethanol." Synlett 2010, no. 19 (October 22, 2010): 2971–72. http://dx.doi.org/10.1055/s-0030-1258840.

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3

JALILI, S., and M. AKHAVAN. "A MOLECULAR DYNAMICS SIMULATION STUDY OF CONFORMATIONAL CHANGES AND SOLVATION OF Aβ PEPTIDE IN TRIFLUOROETHANOL AND WATER." Journal of Theoretical and Computational Chemistry 08, no. 02 (April 2009): 215–31. http://dx.doi.org/10.1142/s0219633609004769.

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Molecular dynamics (MD) simulations of amyloid beta peptide have been performed in aqueous solutions of trifluoroethanol with different concentrations. The amount of α-helical secondary structure increases when going from pure water to trifluoroethanol-rich solutions. The conformation obtained in 40% (v/v) trifluoroethanol solution is very similar to the experimental observations of beta peptide in sodium dodecyl sulfate micelle. In this solution, the peptide has two helical segments connected through a looped region. The C-terminal helix of beta peptide unfolds in pure water. The effect of trifluoroethanol on peptide's secondary structure has been explained using the properties calculated from MD trajectories.

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4

Norcross, Bruce E., William C. Lewis, Huifa Gai, Nazih A. Noureldin, and Donald G. Lee. "The oxidation of secondary alcohols by potassium tetraoxoferrate(VI)." Canadian Journal of Chemistry 75, no. 2 (February 1, 1997): 129–39. http://dx.doi.org/10.1139/v97-017.

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The kinetics of the oxidation of 2-propanol, 1,1,1-trifluoro-2-propanol, 1,1,1,3,3,3-hexafluoro-2-propanol, 1-phenyl-2,2,2-trifluoroethanol, 1-(4-methylphenyl)-2,2,2-trifluoroethanol, 1-(3-bromophenyl)-2,2,2-trifluoroethanol, and 1-(3-nitrophenyl)-2,2,2-trifluoroethanol by potassium tetraoxoferrate(VI) have been studied under basic conditions. The products are ketones, formed in almost quantitative yields, iron(III) hydroxide, and dioxygen. The reactions are characterized by substantial enthalpies of activation (40–60 kJ/mol), very unfavorable entropies of activation, large primary deuterium isotope effects, and a positive Hammett ρ value. Both acid and base catalysis are observed. Acid catalysis is attributed to formation of a more reactive oxidant, HFeO4−, at low pH. Base catalysis is attributed partly to the conversion of the reductants to alkoxide ions at high pH, and partly to the reaction of hydroxide ion with tetraoxoferrate(VI) to give a five-coordinated species, HOFeO43−, that reacts rapidly with nucleophiles. A reaction mechanism involving formation of an intermediate ferrate ester is proposed. Keywords: oxidation, alcohols, potassium tetraoxoferrate(VI), ferrate esters, base catalysis, acid catalysis.

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5

Ferber, PH, GE Gream, and TI Stoneman. "The 9-Decalyl and Related cations VII. Solvolysis of 3-(Cyclohex-1′-enyloxy)propyl p-Nitrobenzenesulfonate." Australian Journal of Chemistry 38, no. 5 (1985): 699. http://dx.doi.org/10.1071/ch9850699.

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The solvolysis of 3-(cyclohex-1′-enyloxy) propyl p- nitrobenzenesulfonate (5) in ethanol buffered separately with sodium ethoxide and triethylamine and 2,2,2-trifluoroethanol buffered with triethylamine has been investigated. Kinetic determinations and product studies have been carried out. In ethanol buffered with sodium ethoxide , π-bond participation in the above ester occurs to the extent of 30%; this is raised to 84% when triethylamine is used as the buffering agent. With buffered trifluoroethanol as solvent, π-bond participation in the ester is complete; kunsat/ksat = 920 and a quantitative yield of cyclized products is obtained. Kinetic evidence indicates a lack of significant involvement of a lone pair on oxygen (enol ether system) in the solvolysis of the sulfonate ester; in trifluoroethanol , the compound solvolyses only 1.15 times more rapidly than does 4-(cyclohex-1′-enyl)butyl p-nitrobenzenesulfonate (2), its carbon analogue.

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6

Netto-Ferreira, J. C., V. Wintgens, and J. C. Scaiano. "Laser flash photolysis study of the photoenols generated from ortho-benzylbenzophenone in different solvents." Canadian Journal of Chemistry 72, no. 6 (June 1, 1994): 1565–69. http://dx.doi.org/10.1139/v94-195.

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Irradiation of ortho-benzylbenzophenone leads to the formation of two (E,E and Z,E) out of the possible four photoenols. Laser flash photolysis studies show that the process involves the intermediacy of a short-lived biradical (τ∼50 ns in methanol) that decays concurrently with the formation of the photoenols. The Z,E enol is very short lived and decays by an allowed 1,5-hydrogen shift to regenerate the starting material; its lifetime is < 30 ns, 280 ns, 1.4 µs, and 90 ns, in benzene, acetonitrile, methanol, and trifluoroethanol, respectively. The Z,E enol is stabilized in hydroxylic solvents, although the acidity of trifluoroethanol seems to promote reketonization. E,E Enol lifetimes range from 80 µs (trifluoroethanol) to 47 µs (benzene) and its decay involves cyclization leading to 10-phenylanthrone following oxidation of the appropriate dihydroanthracene formed initially.

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7

Bardin, Julie, Alan R. Kennedy, Li Ven Wong, Blair F. Johnston, and Alastair J. Florence. "Nicotinamide–2,2,2-trifluoroethanol (2/1)." Acta Crystallographica Section E Structure Reports Online 65, no. 4 (March 11, 2009): o727—o728. http://dx.doi.org/10.1107/s1600536809007594.

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8

Lohani, Sachin, Yuegang Zhang, Leonard J. Chyall, Patricia Mougin-Andres, Francis X. Muller, and David J. W. Grant. "Carbamazepine–2,2,2-trifluoroethanol (1/1)." Acta Crystallographica Section E Structure Reports Online 61, no. 5 (April 16, 2005): o1310—o1312. http://dx.doi.org/10.1107/s1600536805010299.

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9

Malhotra, R., and L. A. Woolf. "Thermodynamic properties of 2,2,2-trifluoroethanol." International Journal of Thermophysics 12, no. 2 (March 1991): 397–407. http://dx.doi.org/10.1007/bf00500760.

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10

Storrs, Richard W., Dagmar Truckses, and David E. Wemmer. "Helix propagation in trifluoroethanol solutions." Biopolymers 32, no. 12 (December 1992): 1695–702. http://dx.doi.org/10.1002/bip.360321211.

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11

Gimenez, Diana, Anica Dose, Nicholas L. Robson, Graham Sandford, Steven L. Cobb, and Christopher R. Coxon. "2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation." Organic & Biomolecular Chemistry 15, no. 19 (2017): 4081–85. http://dx.doi.org/10.1039/c7ob00295e.

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12

Omote, Masaaki, Atsushi Tarui, Masakazu Ueo, Marino Morikawa, Masahiko Tsuta, Sumika Iwasaki, Noriko Morishita, Yukiko Karuo, Kazuyuki Sato, and Kentaro Kawai. "One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams." Synthesis 52, no. 23 (August 17, 2020): 3657–66. http://dx.doi.org/10.1055/s-0040-1707238.

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α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.

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13

Peng, Shan, Yahua Wang, Na Li, and Chong Li. "Enhanced cellular uptake and tumor penetration of nanoparticles by imprinting the “hidden” part of membrane receptors for targeted drug delivery." Chemical Communications 53, no. 81 (2017): 11114–17. http://dx.doi.org/10.1039/c7cc05894b.

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14

Ferretti, Francesco, Florian Korbinian Scharnagl, Anna Dall'Anese, Ralf Jackstell, Sarim Dastgir, and Matthias Beller. "Additive-free cobalt-catalysed hydrogenation of carbonates to methanol and alcohols." Catalysis Science & Technology 9, no. 13 (2019): 3548–53. http://dx.doi.org/10.1039/c9cy00951e.

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15

Thomas, Javix, Isabel Peña, Colton D. Carlson, Yisi Yang, Wolfgang Jäger, and Yunjie Xu. "Structural and dynamical features of the 2,2,2-trifluoroethanol⋯ammonia complex." Physical Chemistry Chemical Physics 22, no. 40 (2020): 23019–27. http://dx.doi.org/10.1039/d0cp03329d.

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16

Hulme, Ashley T., and Derek A. Tocher. "5-Fluorouracil–2,2,2-trifluoroethanol (1/1)." Acta Crystallographica Section E Structure Reports Online 61, no. 11 (October 15, 2005): o3661—o3663. http://dx.doi.org/10.1107/s1600536805032198.

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17

Kim, James C. S., and Laurence S. Kaminsky. "2,2,2-Trifluoroethanol Toxicity in Aged Rats." Toxicologic Pathology 16, no. 1 (January 1988): 35–45. http://dx.doi.org/10.1177/019262338801600105.

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18

Scharge, Tina, Thomas Häber, and Martin A. Suhm. "Quantitative chirality synchronization in trifluoroethanol dimers." Phys. Chem. Chem. Phys. 8, no. 40 (2006): 4664–67. http://dx.doi.org/10.1039/b609868a.

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19

Chagolla, Danny P., and John T. Gerig. "Conformations of Betanova in aqueous trifluoroethanol." Biopolymers 93, no. 10 (May 20, 2010): 893–903. http://dx.doi.org/10.1002/bip.21498.

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20

Bodkin, Michael J., and Julia M. Goodfellow. "Hydrophobic solvation in aqueous trifluoroethanol solution." Biopolymers 39, no. 1 (December 6, 1998): 43–50. http://dx.doi.org/10.1002/(sici)1097-0282(199607)39:1<43::aid-bip5>3.0.co;2-v.

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21

Neuman, Robert C., and John T. Gerig. "Interactions of 2,2,2-trifluoroethanol with melittin." Magnetic Resonance in Chemistry 47, no. 11 (July 24, 2009): 925–31. http://dx.doi.org/10.1002/mrc.2489.

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22

Barnett, S. A., and D. R. Allan. "The high-pressure and low-temperature structural behaviour of 2,2,2-trifluoroethanol." CrystEngComm 21, no. 30 (2019): 4501–6. http://dx.doi.org/10.1039/c9ce00485h.

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23

Wencel-Delord, J., and F. Colobert. "A remarkable solvent effect of fluorinated alcohols on transition metal catalysed C–H functionalizations." Organic Chemistry Frontiers 3, no. 3 (2016): 394–400. http://dx.doi.org/10.1039/c5qo00398a.

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24

Shen, Mengyang, Yuanshuang Xu, Xinying Zhang, and Xuesen Fan. "Synthesis of spirocyclopropylpyrazole derivatives via the cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol." Organic Chemistry Frontiers 9, no. 5 (2022): 1410–16. http://dx.doi.org/10.1039/d1qo01921j.

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Presented herein is a novel synthesis of spirocyclopropylpyrazoles tethered with a trifluoromethyl unit through an unprecedented cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol.

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25

McPherson, Christopher G., Nicola Caldwell, Craig Jamieson, Iain Simpson, and Allan J. B. Watson. "Amidation of unactivated ester derivatives mediated by trifluoroethanol." Organic & Biomolecular Chemistry 15, no. 16 (2017): 3507–18. http://dx.doi.org/10.1039/c7ob00593h.

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26

MacLachlan, L. K., P. I. Haris, D. G. Reid, J. White, D. Chapman, J. A. Lucy, and B. M. Austen. "A spectroscopic study of the mitochondrial transit peptide of rat malate dehydrogenase." Biochemical Journal 303, no. 2 (October 15, 1994): 657–62. http://dx.doi.org/10.1042/bj3030657.

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A peptide corresponding to the N-terminal sequence of the rat malate dehydrogenase, comprising the transit sequence and two residues of the mature protein (MLSALARPVGAALR-RSFSTSAQNNAK) has been chemically synthesized, and its structural characteristics investigated by Fourier-transform i.r. (FT-IR), c.d. and 1H-n.m.r. spectroscopy. FT-IR and c.d. spectra of the peptide were recorded in a variety of environments (aqueous solution, trifluoroethanol) and after incorporation into phospholipid bilayers. The peptide was found to be mainly in aperiodic or undefined conformation in aqueous solution. However, in trifluoroethanol a marked increase in alpha-helical content was observed. An increase in alpha-helical content was also observed in negatively charged lipids (dimyristoylphosphatidylglycerol and cardiolipin). However, when reconstituted in a zwitterionic phospholipid (dimyristoylphosphatidylcholine), no alpha-helical structure was observed. N.m.r. spectroscopy was used to characterize the helical structure in greater detail in trifluoroethanol. The 1H-n.m.r. spectrum of the peptide in this solvent was assigned using standard homonuclear two-dimensional methods. The observed patterns of nuclear Overhauser enhancements confirmed the deductions obtained from c.d. and FT-1R spectroscopy concerning the solution conformation, suggesting a region of flexible nascent helix between Ala-4 and Ser-18. This structure is discussed in terms of the possible function of the peptide.

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27

Chitra, Rajappa, and Paul E. Smith. "A comparison of the properties of 2,2,2-trifluoroethanol and 2,2,2-trifluoroethanol/water mixtures using different force fields." Journal of Chemical Physics 115, no. 12 (September 22, 2001): 5521–30. http://dx.doi.org/10.1063/1.1396676.

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28

Pazderková, Markéta, Eva Kočišová, Tomáš Pazderka, Petr Maloň, Vladimír Kopecký Jr., Lenka Monincová, Václav Čeřovský, and Lucie Bednárová. "Antimicrobial Peptide from the Eusocial BeeHalictus sexcinctusInteracting with Model Membranes." Spectroscopy: An International Journal 27 (2012): 497–502. http://dx.doi.org/10.1155/2012/840956.

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Halictine-1 (Hal-1)—a linear antibacterial dodecapeptide isolated from the venom of the eusocial beeHalictus sexcinctus—has been subjected to a detailed spectroscopic study including circular dichroism, fluorescence, and vibrational spectroscopy. We investigated Hal-1 ability to adopt an amphipathicα-helical structure upon interaction with model lipid-based bacterial membranes (phosphatidylcholine/phosphatidylglycerol-based large unilamellar vesicles and sodium dodecylsulfate micelles) and helix inducing components (trifluoroethanol). It was found that Hal-1 responds sensitively to the composition of the membrane model and to the peptide/lipid ratio. The amphipathic nature of the helical Hal-1 seems to favour flat charged surfaces of the model lipid particles over the nondirectional interaction with trifluoroethanol. Increasing fraction of polyproline II type conformation was detected at low peptide/lipid ratios.

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29

Rostamnia, Sadegh, Asadollah Hassankhani, Hassan Alamgholiloo, and Reza Banaei. "Synthesis of a Zeolitic Imidazolate–Zinc Metal–Organic Framework and the Combination of its Catalytic Properties with 2,2,2-Trifluoroethanol for N-Formylation." Synlett 29, no. 12 (May 30, 2018): 1593–96. http://dx.doi.org/10.1055/s-0037-1610159.

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30

Visentin, Cristina, Susanna Navarro, Gianvito Grasso, Maria Regonesi, Marco Deriu, Paolo Tortora, and Salvador Ventura. "Protein Environment: A Crucial Triggering Factor in Josephin Domain Aggregation: The Role of 2,2,2-Trifluoroethanol." International Journal of Molecular Sciences 19, no. 8 (July 24, 2018): 2151. http://dx.doi.org/10.3390/ijms19082151.

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The protein ataxin-3 contains a polyglutamine stretch that triggers amyloid aggregation when it is expanded beyond a critical threshold. This results in the onset of the spinocerebellar ataxia type 3. The protein consists of the globular N-terminal Josephin domain and a disordered C-terminal tail where the polyglutamine stretch is located. Expanded ataxin-3 aggregates via a two-stage mechanism: first, Josephin domain self-association, then polyQ fibrillation. This highlights the intrinsic amyloidogenic potential of Josephin domain. Therefore, much effort has been put into investigating its aggregation mechanism(s). A key issue regards the conformational requirements for triggering amyloid aggregation, as it is believed that, generally, misfolding should precede aggregation. Here, we have assayed the effect of 2,2,2-trifluoroethanol, a co-solvent capable of stabilizing secondary structures, especially α-helices. By combining biophysical methods and molecular dynamics, we demonstrated that both secondary and tertiary JD structures are virtually unchanged in the presence of up to 5% 2,2,2-trifluoroethanol. Despite the preservation of JD structure, 1% of 2,2,2-trifluoroethanol suffices to exacerbate the intrinsic aggregation propensity of this domain, by slightly decreasing its conformational stability. These results indicate that in the case of JD, conformational fluctuations might suffice to promote a transition towards an aggregated state without the need for extensive unfolding, and highlights the important role played by the environment on the aggregation of this globular domain.

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31

Voskressensky, Leonid G., Alexander A. Titov, Maksad S. Dzhankaziev, Tatiana N. Borisova, Maxim S. Kobzev, Pavel V. Dorovatovskii, Victor N. Khrustalev, Alexander V. Aksenov, and Alexey V. Varlamov. "First synthesis of heterocyclic allenes – benzazecine derivatives." New Journal of Chemistry 41, no. 5 (2017): 1902–4. http://dx.doi.org/10.1039/c6nj03403a.

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Benzazecines with an allene fragment were prepared for the first time and in high yields via tandem reaction of 1-phenylethynyl-1-methyl(benzyl)-1,2,3,4-tetrahydroisoquinolines with activated alkynes in trifluoroethanol.

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32

Attorresi, Cecilia I., Evelyn L. Bonifazi, Javier A. Ramírez, and Gabriel F. Gola. "One-step synthesis of N,N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction." Organic & Biomolecular Chemistry 16, no. 46 (2018): 8944–49. http://dx.doi.org/10.1039/c8ob02229a.

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A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent.

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33

Anderl, Timo, Christophe Audouard, Afjal Miah, Jonathan M. Percy, Giuseppe Rinaudo, and Kuldip Singh. "Syntheses of difluorinated carbasugar phosphates from trifluoroethanol." Organic & Biomolecular Chemistry 7, no. 24 (2009): 5200. http://dx.doi.org/10.1039/b914068a.

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34

van Vliet, Michiel C. A., Isabel W. C. E. Arends, and R. A. Sheldon. "Methyltrioxorhenium-catalysed epoxidation of alkenes in trifluoroethanol." Chemical Communications, no. 9 (1999): 821–22. http://dx.doi.org/10.1039/a902133g.

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35

Burakowski, Andrzej, Jacek Gliński, Bogusława Czarnik-Matusewicz, Paulina Kwoka, Andrzej Baranowski, Kazimierz Jerie, Helge Pfeiffer, and Nikos Chatziathanasiou. "Peculiarity of Aqueous Solutions of 2,2,2-Trifluoroethanol." Journal of Physical Chemistry B 116, no. 1 (December 21, 2011): 705–10. http://dx.doi.org/10.1021/jp210664g.

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36

Kim, James C. S., and Laurence S. Kaminsky. "2,2,2-Trifluoroethanol Toxicity in Hamsters (Mesocricetus auratus)." Toxicologic Pathology 15, no. 4 (June 1987): 417–24. http://dx.doi.org/10.1177/019262338701500405.

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37

Chatterjee, Chiradip, David Martinez, and John T. Gerig. "Interactions of Trifluoroethanol with [val5]angiotensin II." Journal of Physical Chemistry B 111, no. 31 (August 2007): 9355–62. http://dx.doi.org/10.1021/jp0711343.

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38

Chitra, Rajappa, and Paul E. Smith. "Properties of 2,2,2-trifluoroethanol and water mixtures." Journal of Chemical Physics 114, no. 1 (2001): 426. http://dx.doi.org/10.1063/1.1330577.

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39

Mimura, Hideyuki, Akio Watanabe, and Kosuke Kawada. "Catalytic vapor-phase oxidation of 2,2,2-trifluoroethanol." Journal of Fluorine Chemistry 127, no. 4-5 (May 2006): 519–23. http://dx.doi.org/10.1016/j.jfluchem.2005.12.012.

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40

Patel, Sunita T., Jonathan M. Percy, and Robin D. Wilkes. "Functionally diverse monofluorinated vinylic compounds from trifluoroethanol." Tetrahedron Letters 37, no. 29 (July 1996): 5183–86. http://dx.doi.org/10.1016/0040-4039(96)01031-3.

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41

Craig, Heather D., Joshua D. Eklund, and Norbert W. Seidler. "Trifluoroethanol increases albumin’s susceptibility to chemical modification." Archives of Biochemistry and Biophysics 480, no. 1 (December 2008): 11–16. http://dx.doi.org/10.1016/j.abb.2008.09.009.

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42

Fontana, Angelo, Marcello Zambonin, Vincenzo De Filippis, Manuela Bosco, and Patrizia Polverino de Laureto. "Limited proteolysis of cytochrome c in trifluoroethanol." FEBS Letters 362, no. 3 (April 10, 1995): 266–70. http://dx.doi.org/10.1016/0014-5793(95)00237-4.

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43

Lomzov, Aleksandr, Kseniya Ivanova, Inna Pyshnaya, Elena Dmitrienko, and Dmitriy Pyshnyi. "A Comparative Study of the Influence of Aquaous 2,2,2-Trifluoroethanol And Ethanol on the Structural Organization, the Kinetic and Thermodynamic Properties of Oligodeoxyribonucleotides Intermolecular Complex Formation." Siberian Journal of Physics 8, no. 1 (March 1, 2013): 115–24. http://dx.doi.org/10.54362/1818-7919-2013-8-1-115-124.

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A comparative study of the structural organization, thermodynamic and kinetic properties of the oligodeoxynucleotides complexes formation in the presence of 2,2,2-trifluoroethanol and ethanol in aqueous solution (volume fraction of alcohol 0 to 50 %) was performed. No significant changes in the circular dichroism spectra of oligonucleotides and their complexes at the adding of 50 % v/v alcohol into a solution, was observed, and they retain the profile typical for B-form DNA. The study of the thermal stability of DNA duplexes showed that the increase in the volume fraction of ethanol in the aqueous solution up to 50 % results in a linear decrease in the melting temperature of the intermolecular DNA complexes. In the case of the 2,2,2-trifluoroethanol we observed atypical dependence of thermal stability of DNA duplexes on the fraction of the fluorine-containing co-solvent. Increasing the alcohol fraction from 0 to 20% v/v led to a linear decrease of the melting point of the complex. A further increase in the volume fraction of alcohol (up to 50 %) did not change the thermal stability of the duplexes. It was shown, that the destabilizing effect of the two co-solvents is due to the increase of the dissociation rate constant of the complex and has mainly entropic nature. On the example of oligonucleotides complexes of 8, 12, 15 and 20 base pairs length the possibility of prediction DNA duplexes thermal stability was shown. A model taking into account the change of a number solvent molecules interacting with nucleic acids at the duplex formation in aqueous ethanol (50 % v/v) or trifluoroethanol (20 % v/v) was applied. An accuracy of melting temperature prediction was 1.3 and 0.6 degrees. Using this model, we found that the addition of alcohols in solution leads to an increase in the number of water molecules that bind to a complementary pair of nucleotides at the formation of intermolecular complex (in the presence of ethanol or trifluoroethanol 0.51 ± 0.09 and 1.33 ± 0.12, respectively). At the same time, alcohols interacted with single-stranded oligonucleotides and double-stranded in the same way

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44

Tatham, A. S., A. F. Drake, and P. R. Shewry. "Conformational studies of a synthetic peptide corresponding to the repeat motif of C hordein." Biochemical Journal 259, no. 2 (April 15, 1989): 471–76. http://dx.doi.org/10.1042/bj2590471.

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C hordein, a storage protein from barley grains, has an Mr of about 53,000, and consists predominantly of repeated octapeptides with a consensus sequence of Pro-Gln-Gln-Pro-Phe-Pro-Gln-Gln. Previously reported hydrodynamic and c.d. studies indicate the presence of beta-turns, the repetitive nature of which may lead to the formation of a loose spiral. In order to study these turns we have compared the structures of a synthetic peptide corresponding to the consensus repeat motif and total C hordein by using c.d. and Fourier-transform i.r. spectroscopy. The synthetic peptide exhibited spectra typical of beta I/III reverse turns when dissolved in trifluoroethanol at 22 degrees C and in water at 70 degrees C, but ‘random-coil’-like spectra in water at 22 degrees C. The whole protein also showed increases in beta I/III reverse turns when dissolved in increasing concentrations of trifluoroethanol (50-100%, v/v) or heated in ethanol/water (7:3, v/v). Two cryogenic solvent systems were used to determine the c.d. spectra of the peptide and protein at temperatures down to -100 degrees C. Methanol/glycerol (9:1, v/v) and ethanediol/water (2:1, v/v) were selected as analogues of trifluoroethanol/water and water respectively. The peptide exhibited beta I/III-reverse-turn and ‘random-coil’-like spectra in methanol/glycerol and ethanediol/water respectively at 22 degrees C, but a spectrum similar to that of a poly-L-proline II helix in both solvents at -100 degrees C. Similarly the proportion of this spectral type also increased when the whole protein was cooled in both solvents. These results indicate that a poly-L-proline II conformation at low temperatures is in equilibrium with a beta I/III-turn-rich conformation at higher temperatures. The latter conformation is also favoured in solvents of low dielectric constant such as trifluoroethanol. The ‘random-coil‘-like spectra exhibited by the protein and peptide in high-dielectric-constant solvents at room temperature may result from a mixture of the two conformations rather than from the random-coil state.

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Bobrovnik, S. A., M. O. Demchenko, and S. V. Komisarenko. "Effect of trifluoroethanol on antibody reactivity against corresponding and nonrelated antigens." Ukrainian Biochemical Journal 90, no. 4 (June 22, 2018): 80–89. http://dx.doi.org/10.15407/ubj90.04.080.

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Stephenson, W. Kirk, and Richard Fuchs. "Enthalpies of interaction of hydroxylic solutes with organic solvents." Canadian Journal of Chemistry 63, no. 9 (September 1, 1985): 2535–39. http://dx.doi.org/10.1139/v85-419.

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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.

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Yuan, Kejin, Fengying Dong, Xiangcong Yin, Shuai-Shuai Li, Liang Wang, and Lubin Xu. "The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process." Organic Chemistry Frontiers 7, no. 23 (2020): 3868–73. http://dx.doi.org/10.1039/d0qo00972e.

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The dual alkylation of the C(sp³)–H bond of the cyclic α-methyl-N-sulfonyl imine has been achieved through the piperidine-promoted cascade condensation/[1,5]-hydride transfer/cyclization from cyclic α-methyl-N-sulfonyl imine and o-aminobenzaldehyde in trifluoroethanol.

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Samanta, Shampa R., Ruilong Cai, and Virgil Percec. "SET-LRP of semifluorinated acrylates and methacrylates." Polym. Chem. 5, no. 18 (2014): 5479–91. http://dx.doi.org/10.1039/c4py00635f.

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For the first time SET-LRP of 1H,1H,2H,2H-perfluorooctyl acrylate, 2,2,3,3,4,4,4-heptafluorobutyl acrylate, 1H,1H,5H-octafluoropentyl acrylate and 1H,1H,5H-octafluoropentyl methacrylate in 2,2,2-trifluoroethanol as the solvent at 25 °C for acrylates and at 50 °C for methacrylate was accomplished.

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Yang, Hai-Peng, and Hai-Meng Zhou. "Conformational changes of creatine kinase in trifluoroethanol solutions." IUBMB Life 43, no. 6 (December 1997): 1297–304. http://dx.doi.org/10.1080/15216549700205121.

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Köditz, Jens, Ulrich Arnold, and Renate Ulbrich-Hofmann. "Dissecting the effect of trifluoroethanol on ribonuclease A." European Journal of Biochemistry 269, no. 15 (July 25, 2002): 3831–37. http://dx.doi.org/10.1046/j.1432-1033.2002.03079.x.

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