Influence of sigma-hyperconjugative interactions on C-13 substituent chemical shifts: experimental and theoretical study in 1-X,3-CH3-bicyclo[1.1.1]pentanes

C-13 chemical shifts were measured for 18 1-X,3-CH3-bicyclo[1.1.1]pentanes and the corresponding C-13 substituent chemical shifts (SCSs) were compared with those measured previously for the corresponding I-X-bicyclo[1.1.1] pentanes. DFT-B3LYP calculations of GIAO magnetic shielding constants and of...

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Bibliographic Details
Published inMagnetic resonance in chemistry Vol. 42; pp. S202 - S206
Main Authors Contreras, RH, Esteban, AL, Diez, E, Della, EW, Lochert, IJ
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.10.2004
Subjects
Chemistry
Chemistry, Multidisciplinary
Chemistry, Physical
Physical Sciences
Science & Technology
Spectroscopy
Technology
C-13-C-13 COUPLING-CONSTANTS
NONBONDED INTERACTIONS
SPIN
STRUCTURAL DEPENDENCE
NMR SHIFTS
C-13 SCS
sigma-hyperconjugative interactions
bicyclo[1.1.1]pentanes
SATURATED HETEROCYCLES
NMR
SENSITIVE DETECTORS
C-13 NMR
substituent effects
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Summary:C-13 chemical shifts were measured for 18 1-X,3-CH3-bicyclo[1.1.1]pentanes and the corresponding C-13 substituent chemical shifts (SCSs) were compared with those measured previously for the corresponding I-X-bicyclo[1.1.1] pentanes. DFT-B3LYP calculations of GIAO magnetic shielding constants and of natural bond orbitals were carried out in order to gain an insight into factors defining the observed differences in C-13 SCSs in both series. These differences are rationalized in terms of substituent effects on sigma-hyperconjugative interactions. Copyright (C) 2004 John Wiley Sons, Ltd.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1471