Deviations from C3 symmetry of the tri-O-thymotide molecule in different crystalline environments.

Williams, David J.; Lawton, D. M.

doi:10.1016/s0040-4039(00)72484-1

Cited by 25 publications

(4 citation statements)

References 10 publications

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“…Similar geometric isomers have been observed in other systems: initial investigations of medium-sized rings based on tri- o -thymotide in solution by Stoddard − and the support of these findings using single-crystal X-ray diffraction , and 13 C NMR spectroscopy revealed the presence of isomers. Recently, conformational diastereomers of a related trianthranilide have been isolated …”

supporting

confidence: 64%

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

et al. 1997

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supporting

confidence: 64%

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

et al. 1997

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“…-1722 (10) 5025 ( 9) 5609 (5) 2C( 26) 3151( 11) 3080( 10) 8445 (5) 1C (27) -1156 (9) 4242( 9) 5317(4) 2C( 27) 2277 ( 11) 3716( 10) 8141 (5)…”

Section: (4)unclassified

“…1 C(30) -1684 (10) 6488( 9) 6420 (5) 2C( 30) 3779 (10) 1407 (9) 8938(6) 1 C (31) 7358 ( 13) 6026( 12) 6654( 6) 2C( 31) 4723( 13) 1007( 12) 8589( 6)…”

Section: (4)unclassified

Cis-trans photoisomerization in a tri-o-thymotide clathrate. Crystal structure of tri-o-thymotide clathrates of cis- and trans-stilbene

Arad‐Yellin¹,

Brunie²,

Green³

et al. 1979

J. Am. Chem. Soc.

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New clathrate inclusion complexes of tri-o-thymotide (TOT) which contain cfs-stilbene or iraní-stilbene have been prepared and characterized; both crystallize in the triclinic space group PI and have closely similar cell constants. Each unit cell of the ímní-stilbenecomplex contains four TOT molecules and two stilbene molecules; the stilbenes lie on crystallographic centers of symmetry within two crystallographically independent sausage-like channels. The c/T-stilbene-TOT complex contains partially empty channels, the TOT:stilbene ratio being approximately 2.5:1, and the disordered guest molecules could not be located. On irradiation through Pyrex, the m-stilbene-TOT clathrate is transformed to ira/u-stilbene-TOT clathrate; phenanthrene is also formed. The experimental results are consistent with a pathway involving photoisomerization of the c/i-stilbene within the clathrate inclusion complex. The photoreactivity of the rá-stilbene complex, and stability of the transstilbene clathrate, may be ascribed to the disorder, larger volume, and higher energy of the cis species, but we ascribe particular importance to the coincidence or noncoincidence of molecular symmetry and cavity symmetry. The centrosymmetric cavity appears to stabilize centrosymmetric molecules and favor reaction pathways from noncentrosymmetric reactants to centrosymmetric products. The cis and trans isomers of methyl cinnamate also form triclinic TOT clathrate crystals, but here, where neither reactant nor product can achieve the symmetry of the cavity, irradiation yields approximately equal amounts of cis and trans isomer starting from either pure cisor pure rzarw-cinnamate clathrate.

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“…The crystal structure determination of this compound has been carried out as part of a general study of the TOT clathrates. During the course of this work, Williams & Lawton (1975) reported an independent determination of the structure of pure TOT, and also gave details of some previously deterl O 9…”

mentioning

confidence: 99%

The clathrate of tri-o-thymotide (TOT) and pyridine

Brunie¹,

Navaza²,

Tsoucaris³

et al. 1977

Acta Crystallogr Sect B

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Deviations from C3 symmetry of the tri-O-thymotide molecule in different crystalline environments.

Cited by 25 publications

References 10 publications

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Cis-trans photoisomerization in a tri-o-thymotide clathrate. Crystal structure of tri-o-thymotide clathrates of cis- and trans-stilbene

The clathrate of tri-o-thymotide (TOT) and pyridine

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Deviations from C3 symmetry of the tri-O-thymotide molecule in different crystalline environments.

Cited by 25 publications

References 10 publications

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)3·3CA Using 1H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)3·3CA Using 1H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Cis-trans photoisomerization in a tri-o-thymotide clathrate. Crystal structure of tri-o-thymotide clathrates of cis- and trans-stilbene

The clathrate of tri-o-thymotide (TOT) and pyridine

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Product

Resources

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Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)₃·3CA Using ¹H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid