Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates

Thais C. M. Noguiera; Alessandra C. Pinheiro; James L. Wardell; Marcus V. N. De Souza; Jordan Paul Abberley; William T. A. Harrison

doi:10.1107/S2056989015010440

Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates

Thais C. M. Noguiera, Alessandra C. Pinheiro, James L. Wardell, Marcus V. N. De Souza, Jordan Paul Abberley, William T. A. Harrison

Chemistry

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Abstract

The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-
methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tertbutyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopropan-2-yl]-carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H O hydrogen bonds, but with significant differences between them.

Original language	English
Pages (from-to)	752-756
Number of pages	5
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
DOIs	https://doi.org/10.1107/S2056989015010440
Publication status	Published - 2015

Keywords

carbohydrazide
methylation
hydrogen bonds
chain
crystal structure

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Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates
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Noguiera, T. C. M., Pinheiro, A. C., Wardell, J. L., De Souza, M. V. N., Abberley, J. P., & Harrison, W. T. A. (2015). Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates. Acta Crystallographica Section E: Structure Reports Online, 71, 752-756. https://doi.org/10.1107/S2056989015010440

Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates. / Noguiera, Thais C. M.; Pinheiro, Alessandra C.; Wardell, James L. et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, 2015, p. 752-756.

Research output: Contribution to journal › Article › peer-review

Noguiera, TCM, Pinheiro, AC, Wardell, JL, De Souza, MVN, Abberley, JP & Harrison, WTA 2015, 'Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates', Acta Crystallographica Section E: Structure Reports Online, vol. 71, pp. 752-756. https://doi.org/10.1107/S2056989015010440

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title = "Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates",

abstract = "The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tertbutyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopropan-2-yl]-carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H O hydrogen bonds, but with significant differences between them. ",

keywords = "carbohydrazide, methylation, hydrogen bonds, chain, crystal structure",

author = "Noguiera, {Thais C. M.} and Pinheiro, {Alessandra C.} and Wardell, {James L.} and {De Souza}, {Marcus V. N.} and Abberley, {Jordan Paul} and Harrison, {William T. A.}",

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T1 - Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates

AU - Noguiera, Thais C. M.

AU - Pinheiro, Alessandra C.

AU - Wardell, James L.

AU - De Souza, Marcus V. N.

AU - Abberley, Jordan Paul

AU - Harrison, William T. A.

PY - 2015

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N2 - The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tertbutyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopropan-2-yl]-carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H O hydrogen bonds, but with significant differences between them.

AB - The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tertbutyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopropan-2-yl]-carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H O hydrogen bonds, but with significant differences between them.

KW - carbohydrazide

KW - methylation

KW - hydrogen bonds

KW - chain

KW - crystal structure

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DO - 10.1107/S2056989015010440

M3 - Article

SN - 1600-5368

VL - 71

SP - 752

EP - 756

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

ER -

Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates

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Keywords

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