NMR spectroscopic study of coupling effects

Bzhezovskii, V. M.; Калабин, Г. А.; Чмутова, Г. А.; Трофимов, Б. А.

doi:10.1007/bf01179459

Cited by 2 publications

(4 citation statements)

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“…Turning to the selenides, it is striking that 6(C-4) is the same in 4-tert-butyl phenyl selenide (26) as in the corresponding sulfide (19). Therefore eq.…”

Section: Resultsmentioning

confidence: 99%

“…6(C-4) for the alkyl phenyl sulfides (19) is written as eq. [7], where 128.5 is the "C chemical shift of benzene (26). For thioanisole in solution, (cos2 0) is 0.74 (37), yielding A as 5.'11.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore eq. [7] is appropriate for the selenides, and their chemical shifts (26) then yield the (sin2 0) values in 3~ relationship between S(C-4) and sin2 0 has previously been assumed for some alkyl phenyl ketones (45). in the sulfides.…”

Section: Resultsmentioning

confidence: 99%

“…The K e n effect in solution has 8 as 32" (25). The 13C nmr chemical shifts of neat alkyl phenyl selenides (26,27) bear out the intuition that p.. .T conjugation decreases in the order 0 > S > Se. Hence nonplanar conformations will be increasingly favored in that order.…”

Section: Introductionmentioning

confidence: 99%

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Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Schaefer¹,

Penner²

1988

Can. J. Chem.

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. Can. J. Chem. 66, 1641 (1988). The long-range spin-spin coupling constant over six bonds between the "F nucleus and the I3C nucleus in the side chain, 6~( C ,~) , is reported for 4--F--C6H4-X-R, where X = 0 , S and R = CH3, CH2CH3, CH(CH3)? and C(CH3),. 6~(~,~) depends on sin2 0, where 0 is the angle by which the side chain twists out-of-plane about the C, -X bond. Expectation values of sin2 0 are obtained from 6~(C,F), yielding magnitudes of the apparent twofoldbarrier to rotation about the CW2-X bond. In these terms, the most stable conformation is that for 0 = 0" for all compounds, with the exception of R = C(CH3)3 and of X = S, R = CH(CH3)'; there is effectively free rotation about the C,r--S bond in isopropyl4-fluorophenyl sulfide in acetone-d6 solution. Good correlations exist between 6~( C ,~) and a number of other molecular properties, including certain differences of ionization potentials of the molecular orbitals in the ethers. In particular, the chemical shifts of C-4 are correlated with 6~( C ,~) . Because J(C,C), the coupling constant involving C-4, also depends on sin' 0, it is measured for the methyl and ethyl selenides and tellurides, as are other l3C,I3C couplings involving a I3C nucleus in the side chain. The literature values for the I3C nuclear magnetic resonance chemical shifts in alkyl phenyl selenides and tellurides can be related to 0 preferences and also allow estimates of the extrema in 'J(C,C). The resultant values of arcsin (sin' 0)"' for R = CH3 are in good agreement with estimates of 0 obtained from electron diffraction patterns, photoelectron spectra, and nuclear magnetic resonance in the nematic phase.

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“…Turning to the selenides, it is striking that 6(C-4) is the same in 4-tert-butyl phenyl selenide (26) as in the corresponding sulfide (19). Therefore eq.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Schaefer¹,

Penner²

1988

Can. J. Chem.

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Electronic and Conformational Structure of Aromatic Thiols and Their Derivatives

Aliyev

Трофимов

Опарина

2021

Aromatic Thiols and Their Derivatives

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NMR spectroscopic study of coupling effects

Cited by 2 publications

References 1 publication

Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Electronic and Conformational Structure of Aromatic Thiols and Their Derivatives

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NMR spectroscopic study of coupling effects

Cited by 2 publications

References 1 publication

Long-range coupling constants for α-13C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Long-range coupling constants for α-13C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Electronic and Conformational Structure of Aromatic Thiols and Their Derivatives

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Product

Resources

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Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information

Long-range coupling constants for α-¹³C nuclei in phenyl-X-R (X = O,S,Se,Te) derivatives. Internal rotational information