1H and 13C NMR of some α-halo derivatives of o-xylene

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 10113-10122

  Rezende, Daisy De B ^a   Alcantara, M Regina ^a   De Arruda Campos, Ivan P ^a,b   Toscano, Vicente G ^a   Ebeling, Günter ^c   Lopes, Júlio C D ^d  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b PAULISTA UNIVERSITY   (Brazil)

^c FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^d FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ORGANOHALOGEN DERIVATIVE;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030832528     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00352-9     Document Type: Article

References (35)

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7. 13C NMR spectra].
8. Sadtler Standard Carbon-13 NMR Spectra, Sadtler Research Laboratories, Inc.: Philadelphia, PA. 1976-
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11. 1H NMR spectra].
12. unperturbed aromatic-proton signals from a-brominated o-xylenes should lie in the 7.17-7.19 ppm region, as can be discerned from the values of the signals of H-3/5 from 1a and H-3 from 3. The presence of a small deshielding of the signals due to the protons para to the brominated benzylic carbon and some shielding perceptible on the signal of H-5 from 3 hints at the presence of two effects: a through-bond inductive effect, operating also on the para protons, and a through-space, short-range field-effect, reaching the distal ortho proton. For the iodo compounds, use of similar reasoning leads to a 7.13-7.14 ppm region, for the unperturbed proton signal.
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16. the probable error is usually taken to be a fair estimate of the actual experimental uncertainity; actually, -0.6745σ is the lower quartile mark and +0.6745σ is the upper quartile mark: the area under the normal distribution curve comprised between these marks is 50% of the total area.
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