N-Thiocinnamoylmorpholine

Kerr, K. A.; Roey, P. M. A. O. Van

doi:10.1107/s0567740879006087

Cited by 3 publications

(1 citation statement)

References 6 publications

(6 reference statements)

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“…This angle is determined mainly by the non-bonded contacts noted in Table 6. When the less sterically demanding styryl group is introduced in place of the phenyl group as in 4-thiocinnamoylmorpholine (Kerr & Van Roey, 1979c) the torsional angle is reduced below 2 ° with a consequent lengthening of the C-N bond to 1.339 (3) A. Winkler & Dunitz (1971) have shown that most amides deviate from the planar conformation normally assumed to be the lowest-energy form.…”

Section: Discussionmentioning

confidence: 99%

The structure of 1-(2-hydroxythiobenzoyl)piperidine: room-temperature X-ray diffraction and 20 K neutron diffraction study

Roey¹,

Kerr²

1981

Acta Crystallogr Sect B

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Intramolecular steric contacts cause the o-hydroxyphenyl group to be rotated out of the plane of the thioamide moiety by 68.5 (2) ° at 293 K and by 66.4 (3) ° at 20 K. This conformation is similar to those observed for other N,N-dialkylthiobenzamides and shows that intermolecular hydrogen bonding and differences in packing arrangements do not have large effects on the molecular conformation. The neutron diffraction study shows the geometry of the O-H... S hydrogen bond to be typical of hydrogen bonds of intermediate strength.

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Section: Discussionmentioning

confidence: 99%

The structure of 1-(2-hydroxythiobenzoyl)piperidine: room-temperature X-ray diffraction and 20 K neutron diffraction study

Roey¹,

Kerr²

1981

Acta Crystallogr Sect B

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Organic Section

Iball¹

1984

Organic Section

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Crystal Structure of N-Cinnamoyl-8-oxa-6-azabicyclo[3.2.1]octan-7-one

Yamane¹,

Ashida²,

Hashimoto³

et al. 1992

Bulletin of the Chemical Society of Japan

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The crystal structure of the title compound has been determined in order to study the structure-reactivity relationship of a bicyclo compound. C15H15O3, M 257.29, monoclinic, space group P21/a, a = 24.122(6), b = 6.990(2), c = 7.800(2) Å, β = 94.27(2)°, V = 1311.5(6) Å3, Z = 4, Dx = 1.304 g cm−3, μ = 7.56 cm−1 for Kα. The final R-value is 0.062 for 1948 reflections. The molecular structure is essentially the same as that of the N-benzoyl derivative of the bicyclo compound. An elongation of the C–N bond distance in the lactam-amide moiety, which had been found in the N-benzoyl derivative, was observed and compared with that in the unmodified bicyclo compound. There seems to be little extension of the conjugation of the olefinic group to the carbonyl or phenyl groups in a cinnamoyl moiety, according to the C=C and Csp2–Csp2 distances.

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N-Thiocinnamoylmorpholine

Cited by 3 publications

References 6 publications

The structure of 1-(2-hydroxythiobenzoyl)piperidine: room-temperature X-ray diffraction and 20 K neutron diffraction study

The structure of 1-(2-hydroxythiobenzoyl)piperidine: room-temperature X-ray diffraction and 20 K neutron diffraction study

Organic Section

Crystal Structure of N-Cinnamoyl-8-oxa-6-azabicyclo[3.2.1]octan-7-one

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