Secondary deuterium/hydrogen isotope effects on carbon-13 chemical shifts in cycloalkanes. Downfield shifts over three and four bonds

Aydın, Rafet; Guenther, Harald

doi:10.1021/ja00395a090

Cited by 57 publications

(11 citation statements)

References 4 publications

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“…In organic compounds, deuterium-induced shifts of 13 C resonances have been studied extensively and correlations with carbon hybridization and substitution 43 , hyperconjugation 44 , dihedral angles 45 , and spin-spin coupling constants 46 were found. Apart from these aspects which are related to physical organic chemistry, isotope shifts have also been used in a straightforward way as assignment aids in 13 C-NMR [47][48][49] .…”

Section: Isotopementioning

confidence: 99%

Selected topics from recent NMR studies of organolithium compounds

Günther¹

1999

J. Braz. Chem. Soc.

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Após uma breve introdução à espectroscopia de RMN de metais alcalinos e alcalino terrosos, esta revisão concentra-se nas investigações de RMN em compostos organo-lítios. O método de impressão digital isotópica, que baseia-se no deslocamento das ressonâncicas de 6 Li induzido por deutério, é apresentado e exemplificado com aplicações sobre o comportamento de agregação de sistemas de ciclopropil-lítio e formação de agregados mistos entre metil-lítio e sais de lítio. No capítulo seguinte discutem-se experimentos uni-e bidimensionais, tanto para sistemas de spin homonucleares quanto heteronucleares. Finalmente, descrevem-se os aspectos estruturais associados ao benzil-lítio e a formação de sistemas poli-lítio pela redução de bifenilas por lítio. After a short introduction to NMR spectroscopy of alkali and alkaline earth metals the review concentrates on NMR investigations of organolithium compounds. The isotopic fingerprint method, which rests on deuterium-induced isotope shifts for 6 Li resonances, is introduced and exemplified with applications from the aggregation behavior of cyclopropyllithium systems and mixed aggregate formation between methyllithium and lithium salts. In the following chapter, one-and two-dimensional pulse experiments, both for homo-and for heteronuclear spin systems are discussed. Finally, the structural aspects associated with benzyllithium are outlined and the formation of polylithium systems by lithium reduction of biphenylenes is described.

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Section: Isotopementioning

confidence: 99%

Selected topics from recent NMR studies of organolithium compounds

Günther¹

1999

J. Braz. Chem. Soc.

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“…Deuterium isotope effects upon 13C nuclear shieldings, " AC(D) = SC(H) -6C(D) have recently been investigated in some They are usually small, short range and positive.6 A negative isotope effect has been observed in cyclobutene,6 a molecule of fixed geometry. Other unusual isotope effects have been observed in deuterated carbonium ions:-9 amino acids, lo cycloalkanes, [11][12][13][14] c y~l o a l k a n o n e s ,~~~'~ and ketones. 17 The deuterium isotope effects upon 13C nuclear shielding for P-thioxoketones, shown in Table 1 and exemplified in Fig.…”

Section: Qh--ymentioning

confidence: 99%

Deuterium isotope effects on ¹³C nuclear shielding as a measure of tautomeric equilibria

1982

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Large deuterium isotope effects of both signs have been observed on the "C nuclear shielding in proton-chelating tautomeric forms of p-thioxoketones, and small isotope effects of both signs have been found in related forms of Schiffs bases of salicylaldehydes. These effects are interpreted in terms of shifts in the tautomeric equiliiria on deuterium substitution of the enolic proton. The observation of deuterium isotope effects is suggested as a useful method for the detection of fast tautomeric equiliiria in systems of the _ _ following type.

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“…Aydin and Giinther found no A'P(CH)[D] within experimental error for cyclohexane-d, and cyclopropane-d, . 23 Two papers concerned with the calculation of Table 1 gives all the experimental results. Figure 1…”

Section: Hansen and Led22 Reported One Negative A'p(ch)[d]mentioning

confidence: 99%

Deuterium isotope effects on one‐bond carbon, hydrogen coupling constants

Everett

1982

Org. Magn. Reson.

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Secondary deuterium/hydrogen isotope effects on carbon-13 chemical shifts in cycloalkanes. Downfield shifts over three and four bonds

Cited by 57 publications

References 4 publications

Selected topics from recent NMR studies of organolithium compounds

Selected topics from recent NMR studies of organolithium compounds

Deuterium isotope effects on ¹³C nuclear shielding as a measure of tautomeric equilibria

Deuterium isotope effects on one‐bond carbon, hydrogen coupling constants

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Secondary deuterium/hydrogen isotope effects on carbon-13 chemical shifts in cycloalkanes. Downfield shifts over three and four bonds

Cited by 57 publications

References 4 publications

Selected topics from recent NMR studies of organolithium compounds

Selected topics from recent NMR studies of organolithium compounds

Deuterium isotope effects on 13C nuclear shielding as a measure of tautomeric equilibria

Deuterium isotope effects on one‐bond carbon, hydrogen coupling constants

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Product

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Deuterium isotope effects on ¹³C nuclear shielding as a measure of tautomeric equilibria