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

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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 languageEnglish
Pages (from-to)752-756
Number of pages5
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
DOIs
Publication statusPublished - 2015

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Carbamates
Hydrogen
Crystal structure
crystal structure
Methylation
hydrazine
Hydrazine
hydrogen
Hydrogen bonds
Derivatives
Molecules
methylation
hydrazines
Serine
hydrogen bonds
synthesis
molecules

Keywords

  • carbohydrazide
  • methylation
  • hydrogen bonds
  • chain
  • crystal structure

Cite this

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.; De Souza, Marcus V. N.; Abberley, Jordan Paul; Harrison, William T. A.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, 2015, p. 752-756.

Research output: Contribution to journalArticle

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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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