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Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation

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Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation. / Arthur, Richard J. ; Coogan, Michael; Casadesus, Meritxell et al.
In: CrystEngComm, Vol. 11, No. 4, 2009, p. 610-619.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Arthur, RJ, Coogan, M, Casadesus, M, Haigh, R, Headspith, DA, Grazia Francesconi , M & Laye, RH 2009, 'Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation', CrystEngComm, vol. 11, no. 4, pp. 610-619. https://doi.org/10.1039/B814424A

APA

Arthur, R. J., Coogan, M., Casadesus, M., Haigh, R., Headspith, D. A., Grazia Francesconi , M., & Laye, R. H. (2009). Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation. CrystEngComm, 11(4), 610-619. https://doi.org/10.1039/B814424A

Vancouver

Arthur RJ, Coogan M, Casadesus M, Haigh R, Headspith DA, Grazia Francesconi M et al. Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation. CrystEngComm. 2009;11(4):610-619. doi: 10.1039/B814424A

Author

Arthur, Richard J. ; Coogan, Michael ; Casadesus, Meritxell et al. / Stereostructural behaviour of N–N atropisomers : two conglomerate crystallisations and a crystallisation-induced deracemisation. In: CrystEngComm. 2009 ; Vol. 11, No. 4. pp. 610-619.

Bibtex

@article{5dacfe4c2c9c44759f8594d70c43a0bd,
title = "Stereostructural behaviour of N–N atropisomers: two conglomerate crystallisations and a crystallisation-induced deracemisation",
abstract = "The solid state behaviour of a number of compounds which show hindered rotation around an N–N bond, in some cases leading to axial chirality is described. A diacyl hydrazine, bisanthranoly hydrazine, 1 crystallises in the chiral space group P212121, presenting an example of conglomerate crystallisation. A tetra-acyl hydrazine derived from lactic acid, 2, shows kinetic resolution by crystallisation, as of the two isomers observed in the solution NMR, only one crystallises, again in the space group P212121. Two cyclic acyl hydrazines in the form of biquinazolinones are studied: 2,2′diphenyl-3,3-biquinazolinone, 3 crystallises in the achiral space group Pbca, while 3,3′-dimethyl-2,2′-biquinazoline-4′-thio-4-one, 4 crystallises in the chiral space group P21 giving another example of a conglomerate crystallisation. The single crystal structures of each of the species have been compared to powder XRD data to confirm that the single crystal structures are representative of the bulk material.",
author = "Arthur, {Richard J.} and Michael Coogan and Meritxell Casadesus and Robert Haigh and Headspith, {D. A.} and {Grazia Francesconi}, M. and Laye, {Rebecca H.}",
year = "2009",
doi = "10.1039/B814424A",
language = "English",
volume = "11",
pages = "610--619",
journal = "CrystEngComm",
issn = "1466-8033",
publisher = "Royal Society of Chemistry",
number = "4",

}

RIS

TY - JOUR

T1 - Stereostructural behaviour of N–N atropisomers

T2 - two conglomerate crystallisations and a crystallisation-induced deracemisation

AU - Arthur, Richard J.

AU - Coogan, Michael

AU - Casadesus, Meritxell

AU - Haigh, Robert

AU - Headspith, D. A.

AU - Grazia Francesconi , M.

AU - Laye, Rebecca H.

PY - 2009

Y1 - 2009

N2 - The solid state behaviour of a number of compounds which show hindered rotation around an N–N bond, in some cases leading to axial chirality is described. A diacyl hydrazine, bisanthranoly hydrazine, 1 crystallises in the chiral space group P212121, presenting an example of conglomerate crystallisation. A tetra-acyl hydrazine derived from lactic acid, 2, shows kinetic resolution by crystallisation, as of the two isomers observed in the solution NMR, only one crystallises, again in the space group P212121. Two cyclic acyl hydrazines in the form of biquinazolinones are studied: 2,2′diphenyl-3,3-biquinazolinone, 3 crystallises in the achiral space group Pbca, while 3,3′-dimethyl-2,2′-biquinazoline-4′-thio-4-one, 4 crystallises in the chiral space group P21 giving another example of a conglomerate crystallisation. The single crystal structures of each of the species have been compared to powder XRD data to confirm that the single crystal structures are representative of the bulk material.

AB - The solid state behaviour of a number of compounds which show hindered rotation around an N–N bond, in some cases leading to axial chirality is described. A diacyl hydrazine, bisanthranoly hydrazine, 1 crystallises in the chiral space group P212121, presenting an example of conglomerate crystallisation. A tetra-acyl hydrazine derived from lactic acid, 2, shows kinetic resolution by crystallisation, as of the two isomers observed in the solution NMR, only one crystallises, again in the space group P212121. Two cyclic acyl hydrazines in the form of biquinazolinones are studied: 2,2′diphenyl-3,3-biquinazolinone, 3 crystallises in the achiral space group Pbca, while 3,3′-dimethyl-2,2′-biquinazoline-4′-thio-4-one, 4 crystallises in the chiral space group P21 giving another example of a conglomerate crystallisation. The single crystal structures of each of the species have been compared to powder XRD data to confirm that the single crystal structures are representative of the bulk material.

U2 - 10.1039/B814424A

DO - 10.1039/B814424A

M3 - Journal article

VL - 11

SP - 610

EP - 619

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

IS - 4

ER -