Computation Of 3j Hh Coupling Constants With A Combination Of Density Functional Theory And Semiempirical Calculations. Application To Complex Molecules

dc.creatorRichter W.E.
dc.creatorPontes R.M.
dc.creatorAbiko L.A.
dc.creatorGauze G.F.
dc.creatorBasso E.A.
dc.date2012
dc.date2015-06-25T20:25:54Z
dc.date2015-11-26T15:22:55Z
dc.date2015-06-25T20:25:54Z
dc.date2015-11-26T15:22:55Z
dc.date.accessioned2018-03-28T22:32:02Z
dc.date.available2018-03-28T22:32:02Z
dc.identifier
dc.identifierComputational And Theoretical Chemistry. , v. 1001, n. , p. 7 - 14, 2012.
dc.identifier2210271X
dc.identifier10.1016/j.comptc.2012.10.019
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84870292507&partnerID=40&md5=420b76fd4231627cea13dc55caebe8f9
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/90567
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/90567
dc.identifier2-s2.0-84870292507
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1260429
dc.descriptionThis work evaluates the efficiency of economic levels of theory for the prediction of 3J HH spin-spin coupling constants, to be used when robust electronic structure methods are prohibitive. To that purpose, DFT methods like mPW1PW91, B3LYP and PBEPBE were used to obtain coupling constants for a test set whose coupling constants are well known. Satisfactory results were obtained in most of cases, with the mPW1PW91/6-31G(d,p)//B3LYP/6-31G(d,p) leading the set. In a second step, B3LYP was replaced by the semiempirical methods PM6 and RM1 in the geometry optimizations. Coupling constants calculated with these latter structures were at least as good as the ones obtained by pure DFT methods. This is a promising result, because some of the main objectives of computational chemistry - low computational cost and time, allied to high performance and precision - were attained together. © 2012 Elsevier B.V.
dc.description1001
dc.description
dc.description7
dc.description14
dc.descriptionWiitala, K.W., Cramer, C.J., Hoye, T.R., Comparison of various density functional methods for distinguishing stereoisomers based on computed 1H or 13C NMR chemical shifts using diastereomeric penam β-lactams as a test set (2007) Magn. Reson. Chem., 45, pp. 819-829
dc.descriptionBagno, A., Rastrelli, F., Saielli, G., Toward the complete prediction of the 1H and 13C NMR spectra of complex organic molecules by DFT methods: application to natural substances (2006) Chem. Eur. J., 12, pp. 5514-5525
dc.descriptionBarone, G., Gomez-Paloma, L., Duca, D., Silvestri, A., Riccio, R., Bifulco, G., Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts (2002) Chem. Eur. J., 14, pp. 3233-3239
dc.descriptionFacelli, J.C., Calculations of chemical shieldings: theory and applications (2004) Concepts Magn. Reson. Part A, 20 A, pp. 42-69
dc.descriptionSubramaniam, G., Karimi, S., Phillips, D., Solution conformation of longifolene and its precursor by NMR and ab initio calculations (2006) Magn. Reson. Chem., 44, pp. 1118-1121
dc.descriptionRagazzi, M., Carbone, P., Ferro, D.R., Ab initio molecular modeling of 13C NMR chemical shifts of polymers. 1. Ethylene-Norbornene Copolymers (2002) Int. J. Quant. Chem., 88, pp. 663-669
dc.descriptionRychnovsky, S.D., Predicting NMR spectra by computational methods: structure revision of hexacyclinol (2006) Org. Lett., 8, pp. 2895-2898
dc.descriptionGauze, G.F., Pontes, R.M., Basso, E.A., A factorial design analysis of wave functions to be used in calculations of NMR parameters of ketones (2004) J. Mol. Struct. (THEOCHEM), 712, pp. 91-100
dc.descriptionBasso, E.A., Fiorin, B.C., Rittner, R., Conformational behaviour in S-methyl halothioacetates through NMR, FT-IR, and theoretical calculations (2004) Can. J. Chem., 82, pp. 418-426
dc.descriptionTaha, H.A., Castillo, N., Sears, D.N., Wasylishen, R.E., Lowary, T.L., Roy, P., Conformational analysis of arabinofuranosides: prediction of 3J H,H using MD simulations with DFT-derived spin-spin coupling profiles (2010) J. Chem. Theory Comput., 6, pp. 212-222
dc.descriptionVaara, J., Jokisaari, J., Wasylishen, R.E., Bryce, D.L., Spin-Spin coupling tensors as determined by experiments and computational chemistry (2002) Prog. Magn. Reson. Spec., 41, pp. 233-304
dc.descriptionZampella, A., Auria, M.V.D., Paloma, L.G., Casapullo, A., Minale, L., Henin, Y., Callipeltin A, an Anti-HIV cyclic depsipeptide from the new caledonian lithistida sponge Callipelta sp. (1996) J. Am. Chem. Soc., 118, pp. 6202-6209
dc.descriptionBassarello, C., Zampella, A., Monti, M.C., Gomez-Paloma, L., D'Auria, M.V., Riccio, R., Bifulco, G., Quantum mechanical calculation of coupling constants in the configurational analysis of flexible systems: determination of the configuration of Callipeltin A (2006) Eur. J. Org. Chem., pp. 604-609
dc.descriptionJain, R., Bally, T., Rablen, P.R., Calculating accurate proton chemical shifts of organic molecules with density functional methods and modest basis sets (2009) J. Org. Chem., 74, pp. 4017-4023
dc.descriptionPalermo, G., Riccio, R., Bifulco, G., Effect of electronegative substituents and angular dependence on the heteronuclear spin-spin coupling constant 3J(C-H): an empirical prediction equation derived by density functional theory calculations (2010) J. Org. Chem., 75, pp. 1982-1991
dc.descriptionBarone, V., Cossi, M., Tomasi, J., A new definition of cavities for the computation of solvation free energies by the polarizable continuum model (1997) J. Chem. Phys., 107, pp. 3210-3221
dc.descriptionBondi, A., Van der Waals volumes+radii (1964) J. Phys. Chem., 68, pp. 441-451
dc.descriptionFrisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.J.A., Gonzalez, C.J.A., (2004), Pople Gaussian. Wallingford CT: Gaussian, IncStewart, J.J.P., Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements (2007) J. Mol. Mod., 13, pp. 1173-1213
dc.descriptionRocha, G.B., Freire, R.O., Simas, A.M., Stewart, J.J.P., RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I (2006) J. Comput. Chem., 27, pp. 1101-1111
dc.descriptionStewart, J.J.P., http://OpenMOPAC.net, Stewart Computational Chemistry, Version 11.017WDi Micco, S., Chini, M.G., Riccio, R., Bifulco, G., Quantum mechanical calculation of NMR parameters in the stereostructural determination of natural products (2010) Eur. J. Org. Chem., pp. 1411-1434
dc.descriptionRosselli, S., Bruno, M., Maggio, A., Bellone, G., Formisano, C., Mattia, C.A., Di Micco, S., Bifulco, G., Two new flavonoids from bonannia graeca: a DFT-NMR combined approach in solving structures (2007) Eur. J. Org. Chem., pp. 2504-2510
dc.descriptionAav, R., Pehk, T., Tamp, S., Tamm, T., Kudrjašova, M., Parve, O., Lopp, M., Theoretical prediction and assignment of vicinal 1H- 1H coupling constants of diastereomeric 3-alkoxy-6,7-epoxy-2-oxabicyclo[3.3.0]octanes (2011) Magn. Reson. Chem., 49, pp. 76-82
dc.descriptionWilliamson, R.T., Marquez, B.L., Sosa, A.C.B., Koehn, F.E., Relative stereochemical determination of β-hydroxycarbonyl compounds (aldol products) utilizing the J-based configuration analysis method (2003) Magn. Reson. Chem., 41, pp. 379-385
dc.descriptionTormena, C.F., Rittner, R., Abraham, R.J., Basso, E.A., Pontes, R.M., Conformational analysis. Part 33.1 An NMR, solvation and theoretical investigation of conformational isomerism in N,N-dimethylfluoroacetamide and N,N-dimethyl-α-fluoropropionamide (2000) J. Chem. Soc., Perkin Trans., 2, pp. 2054-2059
dc.languageen
dc.publisher
dc.relationComputational and Theoretical Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleComputation Of 3j Hh Coupling Constants With A Combination Of Density Functional Theory And Semiempirical Calculations. Application To Complex Molecules
dc.typeArtículos de revistas


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