<b>Studies in Magnetic Nonequivalence. N.m.r. Spectra of Two-Spin and Two-Spin-Group Systems</b>

Snyder, Eugene I.

doi:10.1021/ja00900a023

Cited by 59 publications

(11 citation statements)

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“…Chem. Soc., 85, 1882(1963. (12) (a) Similar experiments have been reported by Roberts and coworkers: J. D. Roberts, Mechanisms Conference, Corvallis, Ore., 1964; (b) G. M. Whitesides, F. Kaplan, and J. D. Roberts,/.…”

supporting

confidence: 62%

The Kinetics of Inversion of 2-Methylbutylmagnesium Bromide and Related Compounds

Fraenkel¹,

Dix²

1966

J. Am. Chem. Soc.

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supporting

confidence: 62%

The Kinetics of Inversion of 2-Methylbutylmagnesium Bromide and Related Compounds

Fraenkel¹,

Dix²

1966

J. Am. Chem. Soc.

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“…[I] AS = (A)c + (A)i A well-documented phenomenon (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) in proton magnetic resonance spectroscopy is the magnetic nonequivalence of the diastereotopic methylene hydrogens in molecules possessing a -CH,-CXYZ fragment (where X, Y, and Z are different) as is manifested by a typical AB .proton subspectrum. There seems to exist a general consensus that the differential chemical shift (6, -S,, henceforth AS) can be discussed in terms of a temperature-dependent contribution, arising from unequal populations of the rotamers about the C-C bond, and a contribution due to "intrinsic molecular asymmetry" and attempts have been made to assess their relative contributions.…”

Section: Introductionmentioning

confidence: 99%

A Nuclear Magnetic Resonance Study of Nucleoside Conformation in Solution. The Effect of Structure and Conformation on the Magnetic Nonequivalence of the 5′-Methylene Hydrogens

Hruska¹,

Wood²,

McCaig³

et al. 1974

Can. J. Chem.

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The relative chemical shift between the 5'-methylene hydrogens of a number of purine and pyrimidine nucleosides and nucleotides in solution are presented. For structurally related pyrimidine nucleosides in aqueous solution a good correlation between this relative shift and the sum of the 4'-5' hydrogen-hydrogen vicinal coupling constants is noted. For this series of related molecules arguments are presented that the variation in the magnetic nonequivalence of this pair of hydrogens is a consequence of conformational changes about the C4'-C5' bond. Deviations from the correlation plot a r e observed for purine derivatives, nucleoside monophosphates etc. and discussed in terms of the effect of the specific chemical modification upon the nucleoside conformation and upon the intrinsic chemical shift nonequivalence of the 5'-methylene hydrogens.On presente les deplacements chimiques relatifs des hydrogenes appartenant aux groupes mCthylenes-5' pour plusieurs nuclCosides et nuclCotides dCrivCs de la purine et de la pyrimidine en solution. O n remarque un bon accord entre ce deplacement chimique relatif et la somme des constantes de couplage vicinal hydrogene-hydrogene 4'-5' pour les nucleosides dCrivCs de la pyrimidine qui sont relies par leur structure.On apporte des preuves visant a demontrer que la variation de la non-Cquivalence magnetique d' e cette paire d'hydrogenes est une consiquence de changements de conformation autour du lien C4'-C5' pour cette skrie de molCcules. On observe et on discute des Ccarts par rapport a cette relation dans le cas des derives de la purine, des monophosphates de nuclCoside etc. Ces Ccarts seraient d i s a l'effet d e rnodification chimique spCcifique a u niveau de la conformation du nuclkoside et a u niveau de la non-Cquivalence intrinseque des dtplacements chimiques des hydrogenes appartenant aux groupes methylenes-5'.[Traduit par le journal]Can. J . Chem., 52,497 (1974)

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“…Chem. Soc., 86, 1199(1963, and at the 18th National Organic Symposium, Columbus, Ohio, June 19, 1963. (3) For recent reviews, cf. A. Streitwieser, Jr., Ann.…”

mentioning

confidence: 99%

The Stereochemistry of Doubly Bridged Biphenyls: Synthesis, Spectral Properties, and Optical Stability

Mislow¹,

Glass²,

Hopps³

et al. 1964

J. Am. Chem. Soc.

180

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Studies in Magnetic Nonequivalence. N.m.r. Spectra of Two-Spin and Two-Spin-Group Systems

Cited by 59 publications

References 0 publications

The Kinetics of Inversion of 2-Methylbutylmagnesium Bromide and Related Compounds

The Kinetics of Inversion of 2-Methylbutylmagnesium Bromide and Related Compounds

A Nuclear Magnetic Resonance Study of Nucleoside Conformation in Solution. The Effect of Structure and Conformation on the Magnetic Nonequivalence of the 5′-Methylene Hydrogens

The Stereochemistry of Doubly Bridged Biphenyls: Synthesis, Spectral Properties, and Optical Stability

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