Unusual Through-space, Ts, Pathway For The Transmission Of Jfhf Coupling: 2-fluorobenzaldehyde Study Case

dc.creatorFavaro D.C.
dc.creatorContreras R.H.
dc.creatorTormena C.F.
dc.date2013
dc.date2015-06-25T19:18:12Z
dc.date2015-11-26T15:16:03Z
dc.date2015-06-25T19:18:12Z
dc.date2015-11-26T15:16:03Z
dc.date.accessioned2018-03-28T22:25:54Z
dc.date.available2018-03-28T22:25:54Z
dc.identifier
dc.identifierJournal Of Physical Chemistry A. , v. 117, n. 33, p. 7939 - 7945, 2013.
dc.identifier10895639
dc.identifier10.1021/jp402618c
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84883170631&partnerID=40&md5=f50fa3f29ccb9b8ce3eade6f72adbd30
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/89700
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/89700
dc.identifier2-s2.0-84883170631
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1259168
dc.descriptionThe 1H NMR spectra of the title compound in nonpolar and polar solvents and theoretical calculation of spin-spin coupling constants (SSCCs) show that TSJFHf SSCC, where TS stands for "through-space", in polar solvents is amenable to measurement only in the trans conformer. The mechanisms for transmission pathways to such unusual SSCCs are rationalized in terms of the molecular electronic structure. It is stressed that such a result calls for some caution when intending to use TSJFH as a probe to detect the spatial proximity between fluorine and hydrogen atoms. © 2013 American Chemical Society.
dc.description117
dc.description33
dc.description7939
dc.description7945
dc.descriptionPetrakis, L., Sederholm, C.H., NMR Fluorine-Fluorine Coupling Constants in Saturated Organic Compounds (1961) J. Chem. Phys., 35, pp. 1243-1248
dc.descriptionNg, S., Sederholm, C.H., Nuclear Magnetic Resonance Fluorine-Fluorine Coupling Constants (1964) J. Chem. Phys., 40, pp. 2090-2094
dc.descriptionMallory, F.B., Mallory, C.W., Fedarko, M.C., Substituent Effects on Through-Space Fluorine-19-Fluorine-19 Coupling in the 1,8-Difluoronaphthalene System (1974) J. Am. Chem. Soc., 96, pp. 3536-3542
dc.descriptionBarfield, M., Karplus, M., Valence-Bond Bond-Order Formulation for Contact Nuclear Spin-Spin Coupling (1969) J. Am. Chem. Soc., 91, pp. 1-10
dc.descriptionHirao, K., Nakatsuji, H., Kato, H., Yonezawa, T., Theoretical Study of the Fluorine-Fluorine Nuclear Spin Coupling Constants. I. Importance of Orbital and Spin Dipolar Terms (1972) J. Am. Chem. Soc., 94, pp. 4078-4087
dc.descriptionHirao, K., Nakatsuji, H., Kato, H., Yonezawa, T., Theoretical Study of the Fluorine-Fluorine Nuclear Spin Coupling Constants. II. Stereochemical Dependences (1973) J. Am. Chem. Soc., 95, pp. 31-41
dc.descriptionMallory, F.B., Theory Regarding the Role of Lone-Pair Interactions in Through-Space Fluorine-Fluorine Nuclear Spin-Spin Coupling (1973) J. Am. Chem. Soc., 95, pp. 7747-7752
dc.descriptionMallory, F.B., Mallory, C.W., Ricker, W.M., Nuclear Spin-Spin Coupling via Nonbonded Interactions. III. Effects of Molecular Structure on Through-Space Fluorine-Fluorine and Hydrogen-Fluorine Coupling (1975) J. Am. Chem. Soc., 97, pp. 4770-4771
dc.descriptionMallory, F.B., Mallory, C.W., Ricker, W.M., Nuclear Spin-Spin Coupling via Nonbonded Interactions. 4. Fluorine-Fluorine and Hydrogen-Fluorine Coupling in Substituted Benzo[c]phenanthrenes (1985) J. Org. Chem., 50, pp. 457-461
dc.descriptionMallory, F.B., Luzik, E.D., Mallory, C.W., Carroll, P.J., Nuclear Spin-Spin Coupling via Nonbonded Interactions. 7. Effects of Molecular Structure on Nitrogen-Fluorine Coupling (1992) J. Org. Chem., 57, pp. 366-370
dc.descriptionKrcsmar, L., Grunenberg, J., Dix, I., Jones, P.G., Ibrom, K., Ernst, L., Spin-Spin Interactions Across the "cove" in the (Z) and (E) Isomers of 1,1-Difluoro-9,9-bifluorenylidene (2005) Eur. J. Org. Chem., pp. 5306-5312
dc.descriptionHierso, J.-C., Fihri, A., Ivanov, V.V., Hanquet, B., Pirio, N., Donnadieu, B., Rebiere, B., Meunier, P., "through-Space" Nuclear Spin-Spin J PP Coupling in Tetraphosphine Ferrocenyl Derivatives: A 31P NMR and X-ray Structure Correlation Study for Coordination Complexes (2004) J. Am. Chem. Soc., 126, pp. 11077-11087
dc.descriptionHierso, J.-C., Evrad, D., Lucas, D., Richard, P., Cattey, H., Hanquet, B., Meunier, P., "through-Space" 31P Spin-Spin Couplings in Ferrocenyl Tetraphosphine Coordination Complexes: Improvement in the Determination of the Distance Dependence of J PP Constants (2008) J. Organomet. Chem., 693, pp. 574-578
dc.descriptionThomas, D.A., Ivanov, V.V., Butler, I.R., Horton, P.N., Meunier, P., Hierso, J.-C., Coordination Chemistry of Tetra- and Tridentate Ferrocenyl Polyphosphines: An Unprecedented [1,1-Heteroannular and 2,3-Homoannular]- Phosphorus-Bonding Framework in a Metallocene Dinuclear Coordination Complex (2008) Inorg. Chem., 47, pp. 1607-1615
dc.descriptionLoening, N.M., Anderson, C.E., Iskenderian, W.S., Anderson, C.D., Rychnovsky, S.D., Barfield, M., O'Leary, D.J., Qualitative and Quantitative Measurements of Hydrogen Bond Mediated Scalar Couplings in Acyclic 1,3-Diols (2006) Org. Lett., 8, pp. 5321-5323
dc.descriptionTakemura, H., Ueda, R., Iwanaga, T., C-F···HO Hydrogen Bond in 8-Fluoro-4-methyl-1- Naphthol (2009) J. Fluor. Chem., 130, pp. 684-688
dc.descriptionTakemura, H., Kaneko, M., Sako, K., Iwanaga, T., The Intramolecular C-F···HO Hydrogen Bond of 2-Fluorophenyldiphenylmethanol (2009) New J. Chem., 33, pp. 2004-2006
dc.descriptionKreutz, C., Micura, R., (2008) Modified Nucleosides in Biochemistry, Biotechnology and Medicine, p. 3. , Herdewijn, P. Wiley-VCH. Verlag GmbH & Co, KGaA: Weinheim, Germany, Chapter 1
dc.descriptionDingley, J., Grzesiek, S., Direct Observation of Hydrogen Bonds in Nucleic Acid Base Pairs by Internucleotide 2 J NN Couplings (1998) J. Am. Chem. Soc., 120, pp. 8293-8297
dc.descriptionPervushin, K., Ono, A., Fernandez, C., Szyperski, T., Kainosho, M., Wüthrich, K., NMR Scalar Couplings across Watson-Crick Base Pair Hydrogen Bonds in DNA Observed by Transverse Relaxation-Optimized Spectroscopy (1998) Proc. Natl. Acad. Sci. U.S.A., 95, pp. 14147-14151
dc.descriptionCybulski, H., Sadlej, J., A Computational Study of the Nuclear Magnetic Resonance Parameters for Double Proton Exchange Pathways in the Formamide-Formic Acid and Formamide-Formamidine Complexes (2009) Phys. Chem. Chem. Phys., 11, pp. 11232-11242
dc.descriptionBifulco, G., Mangoni, A., 1H-1H Scalar Coupling Across Two Stacked Aromatic Rings: DFT Calculations and Experimental Proof (2008) Magn. Reson. Chem., 46, pp. 199-201
dc.descriptionDračínský, M., Jansa, P., Bour, P., Computational and Experimental Evidence of Through-Space NMR Spectroscopic J Coupling of Hydrogen Atoms (2012) Chem. - Eur. J., 18, pp. 981-986
dc.descriptionPurser, S., Moore, P.R., Swallowb, S., Gouverneur, V., Fluorine in Medicinal Chemistry (2008) Chem. Soc. Rev., 37, pp. 320-330
dc.descriptionKitevski-Leblanc, J.L., Prosser, R.S., Current Applications of 19F NMR to Studies of Protein Structure and Dynamics (2012) Prog. NMR Spectrosc., 62, pp. 1-33
dc.descriptionQin, L., Sheridan, C., Gao, J., Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in 19F NMR (2012) Org. Lett., 14, pp. 528-531
dc.descriptionEdmonds, M.K., Graichen, F.H.M., Gardiner, J., Abell, A.D., Enantioselective Synthesis of α-Fluorinated β 2-Amino Acids (2008) Org. Lett., 10, pp. 885-887
dc.descriptionTrefi, S., Gilard, V., Balayssac, S., Malet-Martino, M., Martino, R., Quality Assessment of Fluoxetine and Fluvoxamine Pharmaceutical Formulations Purchased in Different Countries or via the Internet by 19F and 2D DOSY 1H NMR (2008) J. Pharm. Biomed. Anal., 46, pp. 707-722
dc.descriptionDucati, L.C., Contreras, R.H., Tormena, C.F., Unexpected Geometrical Effects on Paramagnetic Spin-Orbit and Spin-Dipolar 2 J FF Couplings (2012) J. Phys. Chem. A, 116, pp. 4930-4933
dc.descriptionCormanich, R.A., Moreira, M.A., Freitas, M.P., Ramalho, T.C., Anconi, C.P.A., Rittner, R., Contreras, R.H., Tormena, C.F., 1h J FH Coupling in 2-Fluorophenol Revisited: Is Intramolecular Hydrogen Bond Responsible for This Long-Range Coupling? (2011) Magn. Reson. Chem., 49, pp. 763-767
dc.descriptionContreras, R.H., Ducati, L.C., Tormena, C.F., Critical Analysis of the Through-Space Transmission of NMR J FH Spin-Spin Coupling Constants (2012) Int. J. Quantum Chem., 112, pp. 3158-3163
dc.descriptionAlkorta, I., Elguero, J., Denisov, G.S., A Review with Comprehensive Data on Experimental Indirect Scalar NMR Spin-Spin Coupling Constants across Hydrogen Bonds (2008) Magn. Reson. Chem., 46, pp. 599-624
dc.descriptionVilcachagua, J.D., Ducati, L.C., Rittner, R., Contreras, R.H., Tormena, C.F., Experimental, SOPPA(CCSD), and DFT Analysis of Substitutent Effects on NMR 1 J CF Coupling Constants in Fluorobenzene Derivatives (2011) J. Phys. Chem. A, 115, pp. 1272-1279
dc.descriptionWoon, D.E., Dunning, T.H., Gaussian Basis Sets for Use in Correlated Molecular Calculations. III. The Atoms Aluminum through Argon (1993) J. Chem. Phys., 98, pp. 1358-1371
dc.descriptionBarone, V., (1996) Recent Advances in Density Functional Methods, Part i, , Chong, D. P. World Scientific Publishing Co. Singapore
dc.descriptionFrisch, M.J., (2010) Gaussian 09, , revision B.01
dc.descriptionGaussian, Inc. Wallingford, CT
dc.descriptionGeertsen, J., Oddershede, J., 2nd-Order Polarization Propagator Calculations of Indirect Nuclear Spin-Spin Coupling Tensors in the Water Molecule (1984) Chem. Phys., 90, pp. 301-311
dc.descriptionEnevoldsen, T., Oddershede, J., Sauer, S.P.A., Correlated Calculations of Indirect Nuclear Spin-Spin Coupling Constants Using Second-Order Polarization Propagator Approximations: SOPPA and SOPPA(CCSD) (1998) Theor. Chem. Acc., 100, pp. 275-284
dc.descriptionSauer, S.P.A., Second-Order Polarization Propagator Approximation with Coupled-Cluster Singles and Doubles Amplitudes-SOPPA(CCSD): The Polarizability and Hyperpolarizability of Li (1997) J. Phys. B: Atom. Mol. Opt. Phys., 30, pp. 3773-3780
dc.description(2011) Dalton2011, , http://daltonprogram.org, A Molecular Electronic Structure Program, Release 2011
dc.descriptionsee
dc.descriptionMarenich, A.V., Cramer, C.J., Truhlar, D.G., Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions (2009) J. Phys. Chem. B, 113, pp. 6378-6396
dc.descriptionGlendening, E.D., Badenhoop, J.K., Reed, A.E., Carpenter, J.E., Bohmann, J.A., Morales, C.M., Weinhold, F., (2009) NBO 5.9, , http://www.chem.wisc.edu/~nbo5/, Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, Program as implemented in the Gaussian 09 package
dc.descriptionBecke, A.D., Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior (1988) Phys. Rev. A, 38, pp. 3098-3100
dc.descriptionBecke, A.D., Density-Functional Thermochemistry. III. The Role of Exact Exchange (1993) J. Chem. Phys., 98, pp. 5648-5652
dc.descriptionLee, T., Yang, W.T., Parr, R.G., Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density (1988) Phys. Rev. B, 37, pp. 785-789
dc.descriptionRuiz De Azúa, M.C., Giribet, C.G., Vizioli, C.V., Contreras, R.H., Ab Initio IPPP-CLOPPA Approach to Perform Bond Contribution Analysis of NMR Coupling Constants: 1 J (NH) in NH3 as a Function of Pyramidality (1998) J. Mol. Struct.: THEOCHEM, 433, pp. 141-150
dc.descriptionPerez, J.E., Ortiz, F.S., Contreras, R.H., Giribet, C.G., Ruiz De Azúa, M.C., Analysis of the Diamagnetic Spin-Orbital Contribution to Indirect Nuclear Spin-Spin Coupling Constants (1990) J. Mol. Struct.: THEOCHEM, 210, pp. 193-198
dc.descriptionContreras, R.H., Gotelli, G., Ducati, L.C., Barbosa, T.M., Tormena, C.F., Analysis of Canonical Molecular Orbitals to Identify Fermi Contact Coupling Pathways. 1. Through-Space Transmission by Overlap of 31P Lone Pairs (2010) J. Phys. Chem. A, 114, pp. 1044-1051
dc.descriptionSoncini, A., Lazzeretti, P., Nuclear Spin-Spin Coupling Density Functions and the Fermi Hole (2003) J. Chem. Phys., 119, pp. 1343-1349
dc.descriptionAutschbach, J., Le Guennic, B., Analyzing and Interpreting NMR Spin-Spin Coupling Constants Using Molecular Orbital Calculations (2007) J. Chem. Educ., 84, pp. 156-171
dc.languageen
dc.publisher
dc.relationJournal of Physical Chemistry A
dc.rightsfechado
dc.sourceScopus
dc.titleUnusual Through-space, Ts, Pathway For The Transmission Of Jfhf Coupling: 2-fluorobenzaldehyde Study Case
dc.typeArtículos de revistas


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