Heavy halogen atom effect on 13C NMR chemical shifts in monohalo derivatives of cyclohexane and pyran. Experimental and theoretical study

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As a first step, a qualitative analysis of the spin-orbit operator was performed to predict the kind of organic compounds, where it could be expected that the SO/FC (spin-orbit/Fermi contact) and SO/SD (spin-orbit/spin dipolar) yield unusually small contributions to the "heavy atom effect"...

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Detalles Bibliográficos
Autor principal: Neto, A.C
Otros Autores: Ducati, L.C, Rittner, R., Tormena, C.F, Contreras, Rubén Horacio, Frenking, G.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2009
Acceso en línea:Registro en Scopus
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Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Neto, A.C. 
245 1 0 |a Heavy halogen atom effect on 13C NMR chemical shifts in monohalo derivatives of cyclohexane and pyran. Experimental and theoretical study 
260 |c 2009 
270 1 0 |m Rittner, R.; Chemistry Institute, State University of Campinas, Caixa Postal 6154, 13084-971 Campinas, SP, Brazil; email: rittner@iqm.unicamp.br 
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506 |2 openaire  |e Política editorial 
520 3 |a As a first step, a qualitative analysis of the spin-orbit operator was performed to predict the kind of organic compounds, where it could be expected that the SO/FC (spin-orbit/Fermi contact) and SO/SD (spin-orbit/spin dipolar) yield unusually small contributions to the "heavy atom effect" on 13C SCSs (substituent chemical shifts). This analysis led to the conclusion that compounds presenting strong hyperconjugative interactions involving the σ*C-X orbital (X = halogen) are good examples where such effects can be expected to take place. On the basis of such results, the following set of model compounds was chosen: 2-eq-halocyclohexane (2-eq), 2-ax-halocyclohexane (2-ax), and 2-ax-halopyran (3), to measure 13C SCSs. Such experimental values, as well as those of methane and halomethanes taken from the literature, were compared to calculated values at a nonrelativistic approach using B3LYP, and at a relativistic approach with BP86 using scalar ZORA, spin-orbit ZORA, scalar PAULI, and spin-orbit PAULI. Results from relativistic calculations are in agreement with the trends predicted by the qualitative model discussed in this work. © 2009 American Chemical Society.  |l eng 
593 |a Chemistry Institute, State University of Campinas, Caixa Postal 6154, 13084-971 Campinas, SP, Brazil 
593 |a Department of Physics, FCEyN, University of Buenos Aires and CONICET, Buenos Aires, Argentina 
593 |a Philipps-Universität Marburg, Hans-Meerwein-Strasse, Marburg, Germany 
700 1 |a Ducati, L.C. 
700 1 |a Rittner, R. 
700 1 |a Tormena, C.F. 
700 1 |a Contreras, Rubén Horacio 
700 1 |a Frenking, G. 
773 0 |d 2009  |g v. 5  |h pp. 2222-2228  |k n. 9  |p J. Chem. Theory Comput.  |x 15499618  |t Journal of Chemical Theory and Computation 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_15499618_v5_n9_p2222_Neto  |x handle  |y Handle 
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963 |a VARI 

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