Hindered rotation in 1,2-dineopentyltetramethylbenzene

Dix, Don T.; Fraenkel, Gideon; Karnes, Harold A.; Newman, Matthew

doi:10.1016/s0040-4039(00)72914-5

Cited by 24 publications

(13 citation statements)

References 2 publications

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“…observation of individual rotamers. The compounds studied in this manner include 2,6-disubstituted benzyl halides (17), 2,6-dichlorobenzal chloride (l8), 2,4,6-trimethylcumene (19), di-t-butylanisylcarbinol (20), and 1,2,3,4-tetramethyl-5,6-dineopentylbenzene (21). In addition, Can.…”

Section: Discussion Of Resultsmentioning

confidence: 99%

The Effect of Substituents on Geminal Proton–Proton Coupling Constants; a Conformational Dependence. II

Fraser¹,

Renaud²

1971

Can. J. Chem.

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The effect of para-substituents on the geminal coupling constants in benzylic methylene groups has been studied as a function of the conformation at the benzene-CH2 bond. The slopes of Hammett plots of J,,,,, us. o are large (-1.6 to -1.9) when the geometry permits a hyperconjugative interaction between the benzene ring and the methylene group but negligible (i-0.2) when this interaction is geometrically restricted. The effect of a change in electronegativity of the group attached to the methylene carbon has also been investigated. The change in the slope, p, from -1.7 to -1.6 on protonation of the nitrogen attached to the methylene group in a series of isoindolines shows this effect to be extremely small. Solvent effects on p are also very small. The potential of this J-o relation for conformational analysis of benzyl groups is discussed in comparison with existing methods.

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Section: Discussion Of Resultsmentioning

confidence: 99%

The Effect of Substituents on Geminal Proton–Proton Coupling Constants; a Conformational Dependence. II

Fraser¹,

Renaud²

1971

Can. J. Chem.

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“…Hindered rotation about the CAr---CH2 bonds in dineopentylprehnitene in solution, as studied by NMR methods, is described by Dix et al (1966).…”

Section: Commentmentioning

confidence: 99%

Dineopentylprehnitene (1,2,3,4-tetramethyl-5,6-dineopentylbenzene) at 296 and 223K

Gerkin¹

1999

Acta Crystallogr C

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“…The first recorded instance of rotation about an sp 3 -sp 2 carbon-carbon single bond giving rise to a dnmr phenomenon is due to Dix et al (1966), who determined the rotational barrier of the neopentyl groups in (ΧΠΙ) (Entry 1, Table III) by observing the collapse of the anisochronicity of the methylene protons with increase in temperature. Since then, a large number of examples has been reported (Table III) and these include systematic studies in series of related compounds as well as a number of interesting isolated observations.…”

Section: ιπ Rotation About Sp 3 -Sp 2 Carbon-carbon Single Bondsmentioning

confidence: 99%

“…Hawkins et al (1971) Hawkins et al (1971) Hawkins et al (1971) Hawkins et al (1971) Hawkins et al (1971) Hawkins et al (1971 Anderson and Pearson (1971a) Anderson and Pearson (1971a) Anderson and Pearson (1971b) Anderson and Pearson (1971b) Anderson and Pearson (1971b) Anderson and Pearson (1971b) Anderson and Pearson (1971b) Anderson and Pearson (1971b) Anderson and Pearson (1972a) Anderson and Pearson (1972a) Anderson and Pearson (1972a) Anderson and Pearson (1972b) Anderson and Pearson (1972b) Anderson and Pearson (1972b) Anderson and Pearson (1972b) Anderson and Pearson (1972b) Bushweller and Anderson (1972) Bushweller and Anderson (1972) Dix et al (1966) Rieker and Kessler (1969) Rieker and Kessler (1969) Rieker and Kessler (1969) ) Siddall and Stewart (1968a, 1969b Siddall and Stewart (1969b) Siddall and Stewart (1969b) Siddall and Stewart (1969b) Siddall and Stewart (1969b); Bartle et al (1970) Siddall and Stewart (1969b…”

Section: Referencementioning

confidence: 99%

Rotation about Single Bonds in Organic Molecules

Sternhell¹

1975

Dynamic Nuclear Magnetic Resonance Spectroscopy

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Hindered rotation in 1,2-dineopentyltetramethylbenzene

Cited by 24 publications

References 2 publications

The Effect of Substituents on Geminal Proton–Proton Coupling Constants; a Conformational Dependence. II

The Effect of Substituents on Geminal Proton–Proton Coupling Constants; a Conformational Dependence. II

Dineopentylprehnitene (1,2,3,4-tetramethyl-5,6-dineopentylbenzene) at 296 and 223K

Rotation about Single Bonds in Organic Molecules

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