Conformational analysis of five-membered rings by molecular mechanics: application to nitroxides

Keywords

Nitroxide mediated radical polymerization, Pyrrolidine, Hyperfine coupling, Computational chemistry, Radical

References

• Stereoelectronic effects in organic chemistryPierre Deslongchamps — 1983
• Ab initio study of the pseudorotation and conformational stability of pyrrolidineLuís Carballeira, Ignacio Pérez‐Juste — 1998
• Beta-phosphorylated five membered ring nitroxides. Synthesis and EPR study.Leszek Dembkowski, J.‐P. FINET, Claudine Fréjaville — 1993
• Origin of the Anomeric Effect Revisited. Theoretical Conformation Analysis of 2-Hydroxypiperidine and 2-HydroxyhexahydropyrimidineUlrike Salzner — 1995
• Radiation Damage in Organic Crystals. II. Electron Spin Resonance of (CO2H)CH2CH(CO2H) in β-Succinic AcidC. Heller, Harden M. McConnell — 1960
• Spectroscopic Determination of the Barrier to Planarity in CyclopentaneL. A. Carreira, George J. Jiang, Willis B. Person — 1972
• Synthese von substituierten homotropilidenen durch homo-1,4-eliminierungHorst Kessler, Wilhelm Ott — 1974
• General definition of ring puckering coordinatesDieter Cremer, J. A. Pople — 1975
• Pseudorotation of cyclopentane and its deuterated derivativesL.E. Bauman, Jaan Laane — 1988
• Evaluation of molecular mechanics methods for the calculation of the barriers to planarity and pseudorotation of small ring moleculesR. L. Rosas, C. Cooper, Jaan Laane — 1990
• Analysis of fructofuranose conformations by molecular mechanicsAlfred D. French, V.H. Tran — 1990
• Calculation of puckered rings with analytical gradientsDieter Cremer — 1990
• The Role of Lone Pair Interactions in the Chemistry of the Monosacceharides. The Aromatic EffectsVernon G. S. Box, Veron G. S. Box — 1990
• The relations between torsional and valency angles of cyclopentaneH. J. Geise, C. Altona, C. Romers — 1967
• A Computational Study of Methyl α-D-Arabinofuranoside: Effect of Ring Conformation on Structural Parameters and Energy ProfileM. Gordon, Todd L. Lowary, Christopher M. Hadad — 1999
• The crystal and molecular structures of 2,2,7,7-tetramethyl-1,4-diaza-5-cycloheptanone (2,2,7,7-tetramethyl-5-homopiperazinone) and the corresponding seven-membered-ring nitroxideA. Grand, P. Rey — 1979
• Force field calculations on five membered ring aminoxyl radicals.F. Vila, Paul Tordo, Didier Siri — 1993
• A comparison and chemometric analysis of several molecular mechanics force fields and parameter sets applied to carbohydratesSerge Pérez, Anne Imberty, Søren Balling Engelsen — 1998
• Remeasurements of the structure of potassium-2,2,5,5-tetramethyl-3-caboxypyrroline-1-oxylJ. C. A. Boyens, Gert J. Kruger — 1970
• Recent studies of the anomeric effectEusebio Juaristi, Gabriel Cuevas — 1992

Cited by

• Multifrequency Pulsed EPR and the Characterization of Molecular DynamicsSandra S. Eaton, Gareth R. Eaton — 2015
• Crystal structure of (6E)-2-[(ortho-hydroxy)benzylidene]-1-[4,5-dihydro- 5-(ortho-hydroxy-phenyl)-1,3,4-thiadiazo-2-yl-4-isoproylidenonium]- hydrazine chloride, C18H19ClN4O2SBonell Schmitt, Thomas Gerber, Eric C. Hosten — 2015
• Potential energy surface and proton HFI constants of the cyclopentane radical cationIrina V. Beregovaya, Lyudmila N. Shchegoleva — 2012
• Accurate ab initio prediction of propagation rate coefficients in free-radical polymerization : Acrylonitrile and vinyl chlorideEkaterina I. Izgorodina, Michelle L. Coote — 2006
• A Step Towards High-Molecular-Weight Living/Controlled Polystyrene Using SG1-Mediated PolymerizationMuriel Lansalot, Yohann Guillaneuf, Benoît Luneau — 2010
• Redetermination of the structure of 3-methyl-1,5-diphenyl-4,5-dihydro- 1H-pyrazole, C16H16N2S. Samshuddin, B. Narayana, H.S. Yathirajan — 2013
• Free energy landscapes of the α-d- and β-d-glucopyranose conformations in both vacuum and aqueous solutionGérald Lelong, Marie‐Louise Saboungi, John W. Brady — 2012
• Extension of the Karplus Relationship for NMR Spin-Spin Coupling Constants to Nonplanar Ring Systems: Pseudorotation of CyclopentaneAnan Wu, Dieter Cremer — 2003
• Crystal structure of fac-2-((E)-(2-aminoethylimino)methyl)phenolato- κ3N,N',O) tricarbonyl rhenium(I), C12H11N2O4ReGratien Habarurema, Thomas Gerber, Eric C. Hosten — 2014
• Electron Spin-Lattice Relaxation Mechanisms of Rapidly-Tumbling Nitroxide RadicalsJoshua R. Biller, Hanan Elajaili, Virginia Meyer — 2013
• Redetermination of the crystal structure of endo-2-carboxy-bicyclo[2.2.1]- heptane, C8H12O2Henk Schalekamp, Eric C. Hosten, Richard Betz — 2015
• Crystal structure of (μ2-acetato-κ2O,O’)-(μ2-bromido)-(μ2-oxido)-tetrabromido- triphenylphosphane-κP-triphenylphosphaneoxide-κOdirhenium( IV)), C38H33Br5O4P2Re2Janvier Mukiza, Thomas Gerber, Eric C. Hosten — 2015
• Computational studies of RAFT polymerization-mechanistic insights and practical applicationsMichelle L. Coote, Elizabeth H. Krenske, Ekaterina I. Izgorodina — 2006
• Crystal structure of 4-phenyl-5-(pyridin-2-yl)-1-((pyridin-2-yl)methyl)- 1H-imidazole-2(3H)-thione, C20H16N4SJanvier Mukiza, Thomas Gerber, Eric C. Hosten — 2014
• Crystal structure of tricarbonyl-chlorido-(2E)-2-(6-(E-(2-hydroxyphenylimino) methyl)pyridine-2-yl)methyleneaminophenol-rhenium(I), C22H15ClN3O5ReGratien Habarurema, Thomas Gerber, Eric C. Hosten — 2015
• Crystal structure of trans-((2-aminophenolato-κO)-(2-hydroxyphenylimido- κ2N,O)-bromido-bis(triphenylphosphane)-rhenium(V)) bromide – acetonitrile – water (1:2:1), C52H49Br2N4O3P2ReJanvier Mukiza, Thomas Gerber, Eric C. Hosten — 2015
• Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2SApril Lulama, Richard Betz — 2015
• Nitroxide radicals for low frequency electron paramagnetic resonance imaging (EPRI)Joshua R. Biller — 2014
• Crystal structure of tris(ortho-phenylenediamide-N,N’)-rhenium(VII) bromide, C18H18BrN6ReGratien Habarurema, Thomas Gerber, Eric C. Hosten — 2015
• Crystal structure of (µ2-acetato-κ2O,O’)-(µ2-chlorido)-(µ2-oxido)- bis(dichlorido-triphenylphosphane-rhenium(IV)), C38H33Cl5O3P2Re2Janvier Mukiza, Thomas Gerber, Eric C. Hosten — 2015

Related papers

• Synthesis of pyrrolidine analogues of solaminMeng Wang, Yufeng Chen, Liguang Lou — 2005
• OPTICAL ACTIVATION OF 2-PHENYLPROPIONALDEHYDE VIA SOME 2-SUBSTITUTED PYRROLIDINE ENAMINESH. MATSUSHITA, Yasuko Tsujino, Masao Noguchi — 1978
• Suzuki Reactions with Stable Organic Radicals – Synthesis of Biphenyls Substituted with Nitronyl‐Nitroxide RadicalsChristophe Stroh, Marcel Mayor, Carsten von Hänisch — 2005
• Synthesis of 2-Substituted Pyrrolidine Nitroxide RadicalsSzilvia Gadányi, Tamás Kálai, József Jekő — 2001
• Unstable intermediates. Part CXXXVI. A survey of the magnetic properties of ·PL3 and ·PL4 radicals: the radicals ·P(OH)3+, ·As(OH)4, and (MeO)3ṖO–I. S. Ginns, Shuddhodan P. Mishra, Martyn C. R. Symons — 1973
• Conformational analysis of imidoyl radicals by electron spin resonance spectroscopyAlwyn G. Davies, Jean‐Yves Nédélec, R. Sutcliffe — 1983
• Organometallic peroxy radicals. 4. Electron spin resonance spectra of the radicals produced by reaction of organophosphorus(IV) and organoarsenic(IV) radicals with 17O-enriched oxygenJ. A. Howard, J. C. Tait — 1978
• Theoretical Investigation of Adenine Radicals Generated in Irradiated DNA Components.Stacey D. Wetmore, Russell J. Boyd, Leif A. Eriksson — 1998
• Hyperfine coupling constants for nitroxide spin probes in water and carbon tetrachlorideJ. J. Windle — 1981
• Nitroxide radicals. Part 19. Nuclear magnetic resonance study of [2,2]paracyclophan-4-yl t-butyl nitroxideAlexander R. Forrester, F. A. Neugebauer, Hans Fischer — 1978