Hindered rotation of the dimethylamino and dimethylthioamide groups in two ortho substituted N,N‐dimethylthiobenzamides

Lozach, René; Legrand, Louis; Sandström, Jan

doi:10.1002/mrc.1270070113

Cited by 11 publications

(1 citation statement)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…80 "C). 4-Bromofluorenone was prepared by the diazotization of 4-aminofluorenone (2.0 g) by adding 40 ml of glacial acetic acid and 10 ml of 48% aqueous hydrobromic acid, by cooling in an icehalt bath, and by then adding a solution of 0.45 g of sodium nitrite in 5 ml of water below the surface of the stirring mixture over a period of 10 min. After 8 min more of stirring, 0.1 g of urea was added for a further 8 min of stirring.…”

Section: -Deuteriofluorene (La) 2-bromofluorene (050 G)mentioning

confidence: 99%

The additivity of NMR carbon–carbon spin–spin coupling constants

1979

View full text Add to dashboard Cite

Fl~orene-9-~'C, fl~orenone-9-~'C, acenaphthenone-ll-"C, a~enaphthenone-l2-~~C, 1-methylcydopentanoll-13C and l-methylcycl~pentene-l-~~C were synthesized to obtain J(CC) values between the natural carbons and the labeled carbons. Each of these compounds possessed at least one asymmetric dual-path coupling, i.e., coupling between the labeled carbon and another carbon via simultaneous two-and three-bonded coupling paths. Model "C-labeled compounds were Synthesized where necessary to give expected values of the constituent mono-path couplings. Values of these dual-path couplings (2+3'6 suggested that the observed value is the (at least approximate) algebraic sum of the two constituent J values.

show abstract

Section: -Deuteriofluorene (La) 2-bromofluorene (050 G)mentioning

confidence: 99%

The additivity of NMR carbon–carbon spin–spin coupling constants

1979

View full text Add to dashboard Cite

show abstract

A ¹³C NMR study of hindered rotation in N¹,N¹‐penta‐ and N¹, N¹‐hexa‐methylene‐N²‐substituted‐phenylformamidines

Wawer

1987

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

Rates of rotations about the C-N' partial double bond in a series of six N',N' penta-and six N',N'-hexa-methyleneNz-substituted-phenyformamidines were determined from 13C DNMR line shape analysis.Electron accepting substituents at the phenyl ring increase the barrier to rotation, and electron donating substituents decrease the barrier, compared with the nonsubstituted compound. Linear relationships are shown to exist between AG* and the I3C chemical shifts of the functional carbon or the pK, of formamidines.

show abstract

Bandshape analysis with internal resolution standard. Barriers to internal rotation in 3,5‐dimethyl‐4‐(N,N‐dimethylthio‐carbamoyl)pyrazoles

1977

Self Cite

View full text Add to dashboard Cite

The barriers to rotation of the dimethylamino group in a series of 4-N,N-dimethylthiocarbamoylpyrazoles have been determined by the 'I3n.m.r. technique. For one of the compounds the rate constants have been determined over a temperature interval of 113 degrees by monitoring the exchange rate in the fast and slow exchange regions by the intensity of the resonances of the exchanging protons relative to an internal reference signal, and in the intermediate region by the conventional complete bandshape technique. The entropy and enthalpy of activation have been calculated, and the values obtained by the intensity method are in reasonable agreement with those obtained by the complete bandshape analysis. For the other compounds the usual coalescence approximation has been used. The thiocarbamoylpyrazoles were prepared by reaction between N,N-dimethyl-a,a-diacetylthioacetamide and the appropriate hydrazines.

show abstract

Hindered rotation of the dimethylamino and dimethylthioamide groups in two ortho substituted N,N‐dimethylthiobenzamides

Cited by 11 publications

References 5 publications

The additivity of NMR carbon–carbon spin–spin coupling constants

The additivity of NMR carbon–carbon spin–spin coupling constants

A ¹³C NMR study of hindered rotation in N¹,N¹‐penta‐ and N¹, N¹‐hexa‐methylene‐N²‐substituted‐phenylformamidines

Bandshape analysis with internal resolution standard. Barriers to internal rotation in 3,5‐dimethyl‐4‐(N,N‐dimethylthio‐carbamoyl)pyrazoles

Contact Info

Product

Resources

About

Hindered rotation of the dimethylamino and dimethylthioamide groups in two ortho substituted N,N‐dimethylthiobenzamides

Cited by 11 publications

References 5 publications

The additivity of NMR carbon–carbon spin–spin coupling constants

The additivity of NMR carbon–carbon spin–spin coupling constants

A 13C NMR study of hindered rotation in N1,N1‐penta‐ and N1, N1‐hexa‐methylene‐N2‐substituted‐phenylformamidines

Bandshape analysis with internal resolution standard. Barriers to internal rotation in 3,5‐dimethyl‐4‐(N,N‐dimethylthio‐carbamoyl)pyrazoles

Contact Info

Product

Resources

About

A ¹³C NMR study of hindered rotation in N¹,N¹‐penta‐ and N¹, N¹‐hexa‐methylene‐N²‐substituted‐phenylformamidines