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Journal articles on the topic 'Gauche effect'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Jung, Sebastian, та Joachim Podlech. "Stereoelectronic Effects: The γ-Gauche Effect in Sulfoxides". Journal of Physical Chemistry A 122, № 26 (2018): 5764–72. http://dx.doi.org/10.1021/acs.jpca.8b03729.

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2

Badawi, Hassan M. "Effect of bulk groups substitution on conformational behavior and structure of gauche-gauche cyclopropylmethanol." Journal of Molecular Structure: THEOCHEM 288, no. 1-2 (1993): 93–103. http://dx.doi.org/10.1016/0166-1280(93)90098-v.

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3

Sasanuma, Yuji, and Kentaro Sugita. "The Attractive Gauche Effect of Ethylene Oxides." Polymer Journal 38, no. 9 (2006): 983–88. http://dx.doi.org/10.1295/polymj.pj2006018.

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4

Thiehoff, Christian, Yannick P. Rey, and Ryan Gilmour. "The Fluorine Gauche Effect: A Brief History." Israel Journal of Chemistry 57, no. 1-2 (2016): 92–100. http://dx.doi.org/10.1002/ijch.201600038.

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5

Baranac-Stojanović, Marija, Milovan Stojanović, and Jovana Aleksić. "Theoretical study of azido gauche effect and its origin." New Journal of Chemistry 41, no. 11 (2017): 4644–61. http://dx.doi.org/10.1039/c7nj00369b.

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6

Port, Vinicius C., and Rodrigo A. Cormanich. "There and back again: the role of hyperconjugation in the fluorine gauche effect." Physical Chemistry Chemical Physics 23, no. 32 (2021): 17329–37. http://dx.doi.org/10.1039/d1cp02806e.

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The fluorine gauche effect was revisited by comparing the rotational profile of 1,2-difluoroethane (DFE) with several analogues, such as peroxides and dissulfides. Hyperconjugative effects are the most important ones for the gauche preference of DFE.

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7

Silla, Josué M., Claudimar J. Duarte, Rodrigo A. Cormanich, Roberto Rittner, and Matheus P. Freitas. "Conformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect." Beilstein Journal of Organic Chemistry 10 (April 16, 2014): 877–82. http://dx.doi.org/10.3762/bjoc.10.84.

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The gauche effect in fluorinated alkylammonium salts is well known and attributed either to an intramolecular hydrogen bond or to an electrostatic attraction between the positively charged nitrogen and the vicinal electronegative fluorine atom. This work reports the effect of adding a fluorine atom in 2-fluoroethylamine hydrochloride on the conformational isomerism of the resulting 2,2-difluoroethylamine chloride (2). The analysis was carried out using NMR coupling constants in D2O solution, in order to mimic the equilibrium conditions in a physiological medium, in the gas phase and in implici

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8

Clemans, George B., and Mesfin Alemayehu. "The Gamma Gauche Substituent Effect in 13C NMR1." Tetrahedron Letters 34, no. 10 (1993): 1563–66. http://dx.doi.org/10.1016/0040-4039(93)85007-j.

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9

Alparone, Andrea. "Second Harmonic Generation, Electrooptical Pockels Effect, and Static First-Order Hyperpolarizabilities of 2,2′-Bithiophene Conformers: An HF, MP2, and DFT Theoretical Investigation." Advances in Physical Chemistry 2013 (December 16, 2013): 1–8. http://dx.doi.org/10.1155/2013/394697.

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The static and dynamic electronic (hyper)polarizabilities of the equilibrium conformations of 2,2′-bithiophene (anti-gauche and syn-gauche) were computed in the gas phase. The calculations were carried out using Hartree-Fock (HF), Møller-Plesset second-order perturbation theory (MP2), and density functional theory methods. The properties were evaluated for the second harmonic generation (SHG), and electrooptical Pockels effect (EOPE) nonlinear optical processes at the typical λ=1064 nm of the Nd:YAG laser. The anti-gauche form characterized by the S–C2–C2′–S dihedral angle of 137° (MP2/6-311G*

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10

Wiberg, Kenneth B., Mark A. Murcko, Keith E. Laidig, and Preston J. MacDougall. "Origin of the Gauche Effect in substituted ethanes and ethenes." Journal of Physical Chemistry 94, no. 18 (1990): 6956–59. http://dx.doi.org/10.1021/j100381a008.

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11

Bitencourt, Michelle, Matheus P. Freitas, and Roberto Rittner. "Conformational and stereoelectronic investigation in 1,2-difluoropropane: The gauche effect." Journal of Molecular Structure 840, no. 1-3 (2007): 133–36. http://dx.doi.org/10.1016/j.molstruc.2006.12.021.

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12

Paul, Susann, W. Bernd Schweizer, Graham Rugg, Hans Martin Senn, and Ryan Gilmour. "The fluorine-NHC gauche effect: a structural and computational study." Tetrahedron 69, no. 27-28 (2013): 5647–59. http://dx.doi.org/10.1016/j.tet.2013.02.071.

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13

Sonntag, Louis-Sebastian, Sabine Schweizer, Christian Ochsenfeld, and Helma Wennemers. "The “Azido Gauche Effect”Implications for the Conformation of Azidoprolines." Journal of the American Chemical Society 128, no. 45 (2006): 14697–703. http://dx.doi.org/10.1021/ja0654938.

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14

Exner, Otto, та Václav Jehlička. "Dipole moments and conformation of α-disulphones. The gauche effect". Collection of Czechoslovak Chemical Communications 50, № 10 (1985): 2245–51. http://dx.doi.org/10.1135/cccc19852245.

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The dipole moments of substituted diphenyl disulphones I-III were measured in benzene solution and interpreted by the previously described graphical method. The results suggest an equilibrium of the ap and sc conformations in the ratio 3 : 1, at variance with various empirical rules and theories of the so-called gauche effect. A statistical treatment of X-ray data of various sulphonyl derivatives revealed essentially two preferred conformations: the more stable sc, with a broadened dihedral angle, and the less stable ap.

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15

Ding, Fu-Jiang, and Liang-Fu Zhang. "Gauche effect and PM3 calculation of open-chain polyphosphorus hydrides." International Journal of Quantum Chemistry 60, no. 5 (1996): 1037–44. http://dx.doi.org/10.1002/(sici)1097-461x(1996)60:5<1037::aid-qua10>3.0.co;2-4.

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16

Goodman, Lionel, Hongbing Gu, and Vojislava Pophristic. "Gauche Effect in 1,2-Difluoroethane. Hyperconjugation, Bent Bonds, Steric Repulsion." Journal of Physical Chemistry A 109, no. 6 (2005): 1223–29. http://dx.doi.org/10.1021/jp046290d.

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17

Rodrigues Silva, Daniela, Lucas Azevedo Santos, Trevor A. Hamlin, Célia Fonseca Guerra, Matheus P. Freitas, and F. Matthias Bickelhaupt. "The Gauche Effect in XCH 2 CH 2 X Revisited." ChemPhysChem 22, no. 7 (2021): 641–48. http://dx.doi.org/10.1002/cphc.202100090.

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18

Rychlewska, Urszula, Natalia Waścinska, Beata Warżajtis, and Jacek Gawroński. "Role of the gauche effect and local 1,3-dipole–dipole interactions in stabilizing an unusual conformation of tartarodinitriles." Acta Crystallographica Section B Structural Science 64, no. 4 (2008): 497–503. http://dx.doi.org/10.1107/s0108768108018272.

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This paper reports the synthesis, X-ray and NMR investigations of chiral and meso dinitriles of tartaric acid (tartarodinitriles) and their O,O′-diacetyl and O,O′-dibenzoyl derivatives. While in chiral tartaric acid its esters and NH amides the four-atom carbon chain is overwhelmingly trans, it is gauche in chiral tartarodinitriles. Conversely, meso-tartaric acid, its esters and amides display a tendency for the gauche conformation, but meso-tartarodinitriles usually have the trans conformation. The NMR studies of tartarodinitriles reveal the presence of a conformational equilibrium in solutio

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19

Dionne, P., and M. St-Jacques. "Mechanism of the gauche conformational effect in 3-halogenated 1,5-benzodioxepins." Journal of the American Chemical Society 109, no. 9 (1987): 2616–23. http://dx.doi.org/10.1021/ja00243a012.

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20

IIMORI, Takamasa, Yasushi MURAI, Yasuhiro WAKIZAWA, et al. "2'- and 3'-Substituted Sangivamycins. Conformational Restriction by the Gauche Effect." CHEMICAL & PHARMACEUTICAL BULLETIN 41, no. 4 (1993): 775–77. http://dx.doi.org/10.1248/cpb.41.775.

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21

Oh, Kwang-Im, Woosung Kim, Cheonik Joo та ін. "Azido Gauche Effect on the Backbone Conformation of β-Azidoalanine Peptides". Journal of Physical Chemistry B 114, № 40 (2010): 13021–29. http://dx.doi.org/10.1021/jp107359m.

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22

Fedorov, M. S., and N. I. Giricheva. "Manifestation of the gauche effect in conformers of benzenesulfonic acid hydrazide." Journal of Structural Chemistry 58, no. 2 (2017): 236–43. http://dx.doi.org/10.1134/s0022476617020032.

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23

Thiehoff, Christian, Lukas Schifferer, Constantin G. Daniliuc, Nico Santschi, and Ryan Gilmour. "The influence of electronic perturbations on the Sulfur–Fluorine Gauche Effect." Journal of Fluorine Chemistry 182 (February 2016): 121–26. http://dx.doi.org/10.1016/j.jfluchem.2016.01.003.

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24

Thiehoff, C., M. C. Holland, C. Daniliuc, K. N. Houk, and R. Gilmour. "Can acyclic conformational control be achieved via a sulfur–fluorine gauche effect?" Chemical Science 6, no. 6 (2015): 3565–71. http://dx.doi.org/10.1039/c5sc00871a.

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Herein detailed conformational analyses of β-fluorosulfides, -sulfoxides and -sulfones are disclosed, thus extending the scope of the fluorine gauche effect to the 3<sup>rd</sup> Period (X = SR, SOR, SO<sub>2</sub>R; ϕ<sub>FCCS</sub> ≈ 60°).

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25

Macuvele, Domingos Lusitâneo Pier, Janaína Nones, Jonas V. Matsinhe, et al. "Simultaneous Effect of Reaction Temperature and Concentration of Surfactant in Organo-Bentonite Synthesis." Materials Science Forum 899 (July 2017): 42–47. http://dx.doi.org/10.4028/www.scientific.net/msf.899.42.

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Transmission infrared spectroscopy (FTIR) was used to study the effect of the temperature and concentration of octadecylamine (surfactant) in the conformation state of amine chains incorporated in a bentonite matrix by organophilization process. The temperature is the most important factor in conformational changes-gauche/trans. Whereas the simultaneous increase of the temperature and concentration of surfactant favors the disordered conformation-gauche. This result is very important in the development of organo-bentonite based polymeric nanocomposites because the intercalation of the polymer

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26

Aufiero, Marialuisa, and Ryan Gilmour. "Informing Molecular Design by Stereoelectronic Theory: The Fluorine Gauche Effect in Catalysis." Accounts of Chemical Research 51, no. 7 (2018): 1701–10. http://dx.doi.org/10.1021/acs.accounts.8b00192.

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27

Liu, Yan-Yan, Ying Zhang, Xin-An Zeng, H. El-Mashad, Zhong-Li Pan, and Qi-Jun Wang. "Effect of Pulsed Electric Field on Microstructure of Some Amino Acid Group of Soy Protein Isolates." International Journal of Food Engineering 10, no. 1 (2014): 113–20. http://dx.doi.org/10.1515/ijfe-2013-0033.

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Abstract The effect of a pulsed electric field (PEF) on the microstructure of some amino acids was studied. Raman spectrum was used to determine the effect of PEF on tyrosine, tryptophan, proline residues, histidine, arginine, aliphatic amino acid, disulfide bond, and polypeptide backbone in soy protein isolates (SPI). Results suggested that increasing the intensity of PEF gradually to 50 kV cm−1 led to a reduction in gauche C–S conformation of CCSSCC dihedral angles. The increase of the PEF intensity caused an increase in the gauche–gauche–gauche conformation of the disulfide bond accompanyin

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28

Dionne, P., and M. ST-Jacques. "Repulsive gauche conformational effect. Analysis of seven-membered rings containing endo and exo sulfur atoms." Canadian Journal of Chemistry 68, no. 3 (1990): 513–21. http://dx.doi.org/10.1139/v90-079.

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The so-called repulsive gauche conformational effect associated with sulfur is investigated through a study of 3-methylthio-1,5-benzodioxepin (1) and 3-methylthio-1-benzoxepin (2), together with 3-fluoro- and 3-chloro-1,5-benzodithiepins (3 and 4), by 13C and 1H dynamic nuclear magnetic resonance methods. The results show that, while compounds 2, 3, and 4 exhibit a large amount of the Ce conformation, the TB form predominates for compound 1. Intramolecular stereoelectronic σ–σ* orbital interactions are analyzed, together with several other factors (steric, electrostatic, and solvation), to exp

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29

Andrade, Laize A. F., та Matheus P. Freitas. "Not all third-row elements experience the fluorine gauche effect: β-fluorinated organophosphorus compounds". New Journal of Chemistry 41, № 20 (2017): 11672–78. http://dx.doi.org/10.1039/c7nj02463k.

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Conformational analyses of β-fluorinated organophosphorus compounds were theoretically carried out to probe the role of a possible fluorine–phosphorus gauche effect in conformer stabilization, specifically using a phosphine, a phosphine oxide, phosphinic and phosphonic acids, and the corresponding anions as model compounds.

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30

Cagašová, Kristýna, Maryam Ghavami, Zhong-Ke Yao та Paul R. Carlier. "Questioning the γ-gauche effect: stereoassignment of 1,3-disubstituted-tetrahydro-β-carbolines using 1H–1H coupling constants". Organic & Biomolecular Chemistry 17, № 27 (2019): 6687–98. http://dx.doi.org/10.1039/c9ob01139k.

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31

Zhang, Huaping, та Barbara N. Timmermann. "Withanolide Structural Revisions by 13C NMR Spectroscopic Analysis Inclusive of the γ-Gauche Effect". Journal of Natural Products 79, № 4 (2016): 732–42. http://dx.doi.org/10.1021/acs.jnatprod.5b00648.

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32

Buissonneaud, David Y., Tanja van Mourik, and David O'Hagan. "A DFT study on the origin of the fluorine gauche effect in substituted fluoroethanes." Tetrahedron 66, no. 12 (2010): 2196–202. http://dx.doi.org/10.1016/j.tet.2010.01.049.

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33

Travis, Karl P., and Debra J. Searles. "Effect of solvation and confinement on the trans-gauche isomerization reaction in n-butane." Journal of Chemical Physics 125, no. 16 (2006): 164501. http://dx.doi.org/10.1063/1.2363380.

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34

Engkvist, O., G. Karlström, and P. O. Widmark. "On the origin of the gauche effect. A quantum chemical study of 1,2-difluoroethane." Chemical Physics Letters 265, no. 1-2 (1997): 19–23. http://dx.doi.org/10.1016/s0009-2614(96)01385-1.

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35

Thibaudeau, C., J. Plavec, N. Garg, A. Papchikhin, and J. Chattopadhyaya. "How Does the Electronegativity of the Substituent Dictate the Strength of the Gauche Effect?" Journal of the American Chemical Society 116, no. 9 (1994): 4038–43. http://dx.doi.org/10.1021/ja00088a043.

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36

Santschi, Nico, Christian Thiehoff, Mareike C. Holland, Constantin G. Daniliuc, K. N. Houk, and Ryan Gilmour. "The Sulfur–Fluorine Gauche Effect in Coinage-Metal Complexes: Augmenting Conformational Equilibria by Complexation." Organometallics 35, no. 17 (2016): 3040–44. http://dx.doi.org/10.1021/acs.organomet.6b00564.

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37

Zangi, Ronen, and Stuart A. Rice. "The Effect of Gauche Molecular Conformations on the Phase Diagram of a Langmuir Monolayer." Langmuir 19, no. 14 (2003): 5949–55. http://dx.doi.org/10.1021/la030044w.

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38

Mueller-Plathe, Florian, and Wilfred F. van Gunsteren. "Can Simple Quantum-Chemical Continuum Models Explain the Gauche Effect in Poly(ethylene oxide)?" Macromolecules 27, no. 21 (1994): 6040–45. http://dx.doi.org/10.1021/ma00099a016.

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39

O’Hagan, David, Clair Bilton, Judith A. K. Howard, Lee Knight та David J. Tozer. "The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect". Journal of the Chemical Society, Perkin Transactions 2, № 4 (2000): 605–7. http://dx.doi.org/10.1039/b000205o.

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40

Andrade, Laize A. F., Josué M. Silla, and Matheus P. Freitas. "The gauche effect is governed by internal hydrogen bond in 2-amino-2-methyl-propanol." Journal of Molecular Structure 1072 (August 2014): 203–7. http://dx.doi.org/10.1016/j.molstruc.2014.05.006.

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41

de Rezende, Fátima M. P., Laize A. F. Andrade, and Matheus P. Freitas. "Intramolecular interactions contributing for the conformational preference of bioactive diphenhydramine: Manifestation of the gauche effect." Journal of Molecular Structure 1093 (August 2015): 8–12. http://dx.doi.org/10.1016/j.molstruc.2015.03.033.

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42

Aleksić, Jovana, Milovan Stojanović та Marija Baranac-Stojanović. "Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion". Journal of Organic Chemistry 80, № 20 (2015): 10197–207. http://dx.doi.org/10.1021/acs.joc.5b01779.

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43

Lima, Filipe B. de, Carlos R. M. Cavalcante, Keyla M. N. de Souza, Juliana A. B. da Silva, and Hélcio J. Batista. "Proposal of Calculation Protocols for Implicit Solvation Methods in Conformational Analysis Involving the Gauche Effect." Revista Processos Químicos 9, no. 18 (2015): 118–21. http://dx.doi.org/10.19142/rpq.v9i18.272.

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44

Mukherjee, Prabir K. "Effect of Gauche Molecular Conformations and Molecular Flexibility on the Rotator Phase Transitions of Alkanes." Journal of Physical Chemistry B 116, no. 5 (2012): 1517–23. http://dx.doi.org/10.1021/jp209924n.

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45

Abraham, Raymond J., Eric J. Chambers, and W. Anthony Thomas. "Conformational analysis. Part 22. An NMR and theoretical investigation of the gauche effect in fluoroethanols." Journal of the Chemical Society, Perkin Transactions 2, no. 5 (1994): 949. http://dx.doi.org/10.1039/p29940000949.

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46

Molnar, Istvan Gabor, Eva-Maria Tanzer, Constantin Daniliuc, and Ryan Gilmour. "ChemInform Abstract: Enantioselective Aziridination of Cyclic Enals Facilitated by the Fluorine-Iminium Ion Gauche Effect." ChemInform 45, no. 28 (2014): no. http://dx.doi.org/10.1002/chin.201428086.

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47

Kofranek, Manfred, Alfred Karpfen, and Hans Lischka. "Gauche- versus s-cis-butadiene revisited: a molecular dynamics simulation of the Ar matrix effect." Chemical Physics Letters 189, no. 3 (1992): 281–86. http://dx.doi.org/10.1016/0009-2614(92)85140-6.

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48

Briggs, Caroline R. S., David O’Hagan, Henry S. Rzepa та Alexandra M. Z. Slawin. "Solid state and theoretical evaluation of β-fluoroethyl esters indicate a fluorine-ester gauche effect". Journal of Fluorine Chemistry 125, № 1 (2004): 19–25. http://dx.doi.org/10.1016/j.jfluchem.2003.08.011.

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49

Mohamed, Shifaza, Elizabeth H. Krenske, and Vito Ferro. "The stereoselectivities of tributyltin hydride-mediated reductions of 5-bromo-d-glucuronides to l-iduronides are dependent on the anomeric substituent: syntheses and DFT calculations." Organic & Biomolecular Chemistry 14, no. 10 (2016): 2950–60. http://dx.doi.org/10.1039/c6ob00283h.

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50

Andrade, Laize A. F., Lucas A. Zeoly, Rodrigo A. Cormanich, and Matheus P. Freitas. "Conformational signature of Ishikawa´s reagent using NMR information from diastereotopic fluorines." Beilstein Journal of Organic Chemistry 15 (February 20, 2019): 506–12. http://dx.doi.org/10.3762/bjoc.15.44.

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The active species of the Ishikawa´s reagent [N,N-diethyl-(1,1,2,3,3,3-hexafluoropropyl)amine] is a fluorinating hexafluoropropylamine used to convert alcohols into alkyl fluorides. On the other hand, it is also an example of model compound useful to probe conformational preferences using spectroscopic information from diastereotopic fluorines. Moreover, the possibility of experiencing both the generalized anomeric and gauche effects makes the Ishikawa´s reagent an ideal choice to study the governing stereoelectronic interactions of the conformational equilibrium of organofluorine compounds. T

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