Effect of sulfur oxidation on the transmission mechanism of4JHH NMR coupling constants in 1,3-dithiane

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Long-range 4JHH couplings in 1,3-dithiane derivatives are rationalized in terms of the effects of hyperconjugative interactions involving the S=0 group. Theoretical and experimental studies of 4JHH couplings were carried out in 1,3-dithiane-l-oxide (2), cw-l,3-dithiane-l,3-dioxide (3), l,3-dithiane-...

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Autor principal: Gauze, G.F
Otros Autores: Basso, E.A, Contreras, Rubén Horacio, Tormena, C.F
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2009
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Gauze, G.F. 
245 1 0 |a Effect of sulfur oxidation on the transmission mechanism of4JHH NMR coupling constants in 1,3-dithiane 
260 |c 2009 
270 1 0 |m Tormena, C. F.; Department of Organic Chemistry, Chemistry Institute, University of Campinas, UNICAMP, P.O. Box 6154, CEP: 13084-971 Campinas, Brazil; email: tormena@iqm.unicamp.br 
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506 |2 openaire  |e Política editorial 
520 3 |a Long-range 4JHH couplings in 1,3-dithiane derivatives are rationalized in terms of the effects of hyperconjugative interactions involving the S=0 group. Theoretical and experimental studies of 4JHH couplings were carried out in 1,3-dithiane-l-oxide (2), cw-l,3-dithiane-l,3-dioxide (3), l,3-dithiane-l,l,3-trioxide (4), and 1,3-dithiane-1,1,3,3-tetraoxide (5) compounds. Hyperconjugative interactions were studied with the natural bond orbital, NBO, method. Hyperconjugative interactions involving the LP O, oxygen lone pair and σ*C2-S1 and σ*S1-C6 antibonding orbitals yield an increase of 4JHeq-Heq couplings. Long-range 4JHax-Hax couplings were also observed between hydrogen atoms in axial orientation, which are rationalized as originating in hyperconjugative interactions involving the bonding σC6-h axand antibonding σ*S=O orbitals. The symmetry for orbital interactions is possible only when the S=0 group is in the axial orientation. © 2009 American Chemical Society.  |l eng 
593 |a Departamento de Química, Universidade Estadual de Maringá, CEP-87020-900, Maringá, Brazil 
593 |a Department of Physics, FCEyN, University of Buenos Aires and CONICET, Buenos Aires, Argentina 
593 |a Department of Organic Chemistry, Chemistry Institute, University of Campinas, UNICAMP, P.O. Box 6154, CEP: 13084-971 Campinas, Brazil 
690 1 0 |a 3 DIOXIDES 
690 1 0 |a ANTI BONDINGS 
690 1 0 |a ANTIBONDING ORBITALS 
690 1 0 |a AXIAL ORIENTATIONS 
690 1 0 |a EXPERIMENTAL STUDIES 
690 1 0 |a HYDROGEN ATOMS 
690 1 0 |a HYPERCONJUGATIVE INTERACTIONS 
690 1 0 |a LONE PAIRS 
690 1 0 |a NATURAL BOND ORBITALS 
690 1 0 |a NMR COUPLINGS 
690 1 0 |a ORBITAL INTERACTIONS 
690 1 0 |a ORBITALS 
690 1 0 |a SULFUR OXIDATIONS 
690 1 0 |a TRANSMISSION MECHANISMS 
690 1 0 |a HYDROGEN 
690 1 0 |a OXYGEN 
690 1 0 |a SULFUR 
690 1 0 |a SULFUR COMPOUNDS 
690 1 0 |a COUPLINGS 
700 1 |a Basso, E.A. 
700 1 |a Contreras, Rubén Horacio 
700 1 |a Tormena, C.F. 
773 0 |d 2009  |g v. 113  |h pp. 2647-2651  |k n. 11  |p J Phys Chem A  |x 10895639  |t Journal of Physical Chemistry A 
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