A DFT/GIAO/NBO and experimental study of 13C SCSs in 1-X-bicyclo[1.1.1]pentanes

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The 13C NMR spectra of 24 members of a series of 1-X-bicyclo[1.1.1]pentanes were measured. SCSs on 13C1 were found to linearly correlated with those on 13C3, although the former correspond to deshielding effects and the latter to shielding effects. Even though the 13C1 SCSs follow the same trend as...

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Autor principal: Della, E.W
Otros Autores: Lochert, I.J, Peralta, J.E, Contreras, Rubén Horacio
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: John Wiley and Sons Ltd 2000
Acceso en línea:Registro en Scopus
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040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a Della, E.W. 
245 1 2 |a A DFT/GIAO/NBO and experimental study of 13C SCSs in 1-X-bicyclo[1.1.1]pentanes 
260 |b John Wiley and Sons Ltd  |c 2000 
270 1 0 |m Della, E.W.; Department of Chemistry, Flinders University, Bedford Park, SA 5108, Australia; email: ern.della@flinders.edu.au 
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506 |2 openaire  |e Política editorial 
520 3 |a The 13C NMR spectra of 24 members of a series of 1-X-bicyclo[1.1.1]pentanes were measured. SCSs on 13C1 were found to linearly correlated with those on 13C3, although the former correspond to deshielding effects and the latter to shielding effects. Even though the 13C1 SCSs follow the same trend as α-SCSs in other types of substrates, they are significantly smaller. In order to provide an insight into the different intramolecular interactions that define such a trend, theoretical studies that include SCSs calculated at the GIAO B3LYP/6-311G** level, electron delocalization analysis within the NBO approach at the same level and electrostatic interaction effects on chemical shifts were carried out. Important halogen heavy-atom effects on C3 were observed, suggesting that the spin-orbit interaction is transmitted through space between the bridgehead carbon atoms. Additionally, in a few members of the series X = H, F, CH3, NH2, OCH3, CN, COOH, COCH3), theoretical calculations of the substituent chemical shifts, 13C SCSs, were carried out with particular reference to the C1 position. These theoretical calculations included: (a) full geometry optimizations, (b) magnetic shielding constant calculations using the GIAO (gauge-included atomic orbitals) method within the DFT (density functional theory) approach and (c) natural bond orbital (NBO) analysis of intramolecular charge transfer interactions. Copyright © 2000 John Wiley & Sons, Ltd.  |l eng 
593 |a Department of Chemistry, Flinders University, Bedford Park, SA 5042, Australia 
593 |a Departamento de Física, Fac. de Cie. Exactas y Narurales, Universidad de Buenos Aires, P.1 (1428) Buenos Aires, Argentina 
593 |a Department of Chemistry, Flinders University, Bedford Park, SA 5108, Australia 
593 |a Def. Sci. and Technol. Organisation, Weapons Systems Division, P.O. Box 1500, Salisbury, SA 5108, Australia 
690 1 0 |a 13C NMR 
690 1 0 |a BICYCLO[1.1.1]PENTANES 
690 1 0 |a NMR 
690 1 0 |a SUBSTITUENT CHEMICAL SHIFTS 
700 1 |a Lochert, I.J. 
700 1 |a Peralta, J.E. 
700 1 |a Contreras, Rubén Horacio 
773 0 |d John Wiley and Sons Ltd, 2000  |g v. 38  |h pp. 395-402  |k n. 6  |p Magn. Reson. Chem.  |x 07491581  |w (AR-BaUEN)CENRE-972  |t Magnetic Resonance in Chemistry 
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