2-Hydroxyacetophenone arylhydrazones. Supramolecular arrangements based on C–H · · · O(H), CH · · · O(NO), N–H · · · O(H), N–H · · · O(NO), C–H · · · π or π · · · π interactions

Thomas C. Baddeley, Luciana de Souza Franca, R. Alan Howie, Geraldo M. de Lima, Jan Skakle, Jose Dias de Souza, James L. Wardell, Solange M. S. V. Wardell

Research output: Contribution to journalArticle

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Abstract

Crystal structures, NMR and IR spectra and EI-MS+ of 2-hydroxyacetophenone arylhydrazones, 2-HOC6H4C(Me)=NNHC6H4Y (1: Y = 2-O2N, 3-O2N, 4-O2N, 4-Me, 4-MeO, H and 4-I) are reported. Two polymorphs of (1: Y = 2-O2N), triclinic and orthorhombic forms, have been identified. While strong intramolecular O-H center dot center dot center dot N(H) hydrogen bonds and layers of molecules are found for all solid 1, supramolecular arrangements of individual members are various and are derived from different combinations of intramolecular interactions, which include C-H center dot center dot center dot O(H), C-H center dot center dot center dot O(NO), N-H center dot center dot center dot O(H), N-H center dot center dot center dot O(NO) and C-H center dot center dot center dot pi hydrogen bonds, as well as pi center dot center dot center dot pi stacking interactions. Intermolecular N-H center dot center dot center dot O hydrogen-bonds involving the phenolic OH group are present in (1: Y = H, 4-O2N, 4-Me, 4-MeO and 4-1), but are absent in ortho-and Iri-(1: Y = 20,N) and (1: Y = 3-O2N). Instead, ortho-(1: Y = 2-O2N) exhibits intermolecular C-H center dot center dot center dot O(H) hydrogen bonds, while no intermolecular hydrogen bonds involving the OH group occur in either triclinic-(1: Y = 2-O2N) or (1: Y = 3-O2N). EI+-MS revealed the presence of olgomeric species, such as (nM + M')(+), where n is up to 4, and M' = H, Na or K.

Original languageEnglish
Pages (from-to)213-224
Number of pages12
JournalZeitschrift für Kristallographie
Volume224
Issue number4
DOIs
Publication statusPublished - Sep 2009

Keywords

  • arylhydrazones
  • supramolecular arrangements
  • hydrogen bonds
  • hydrogen-bonded sheets
  • rings
  • 2,4-dinitrophenylhydrazone
  • 4-nitrophenylhydrazone
  • combination
  • framework
  • chains

Cite this

2-Hydroxyacetophenone arylhydrazones. Supramolecular arrangements based on C–H · · · O(H), CH · · · O(NO), N–H · · · O(H), N–H · · · O(NO), C–H · · · π or π · · · π interactions. / Baddeley, Thomas C.; Franca, Luciana de Souza; Howie, R. Alan; de Lima, Geraldo M.; Skakle, Jan; de Souza, Jose Dias; Wardell, James L.; Wardell, Solange M. S. V.

In: Zeitschrift für Kristallographie, Vol. 224, No. 4, 09.2009, p. 213-224.

Research output: Contribution to journalArticle

Baddeley, Thomas C. ; Franca, Luciana de Souza ; Howie, R. Alan ; de Lima, Geraldo M. ; Skakle, Jan ; de Souza, Jose Dias ; Wardell, James L. ; Wardell, Solange M. S. V. / 2-Hydroxyacetophenone arylhydrazones. Supramolecular arrangements based on C–H · · · O(H), CH · · · O(NO), N–H · · · O(H), N–H · · · O(NO), C–H · · · π or π · · · π interactions. In: Zeitschrift für Kristallographie. 2009 ; Vol. 224, No. 4. pp. 213-224.
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abstract = "Crystal structures, NMR and IR spectra and EI-MS+ of 2-hydroxyacetophenone arylhydrazones, 2-HOC6H4C(Me)=NNHC6H4Y (1: Y = 2-O2N, 3-O2N, 4-O2N, 4-Me, 4-MeO, H and 4-I) are reported. Two polymorphs of (1: Y = 2-O2N), triclinic and orthorhombic forms, have been identified. While strong intramolecular O-H center dot center dot center dot N(H) hydrogen bonds and layers of molecules are found for all solid 1, supramolecular arrangements of individual members are various and are derived from different combinations of intramolecular interactions, which include C-H center dot center dot center dot O(H), C-H center dot center dot center dot O(NO), N-H center dot center dot center dot O(H), N-H center dot center dot center dot O(NO) and C-H center dot center dot center dot pi hydrogen bonds, as well as pi center dot center dot center dot pi stacking interactions. Intermolecular N-H center dot center dot center dot O hydrogen-bonds involving the phenolic OH group are present in (1: Y = H, 4-O2N, 4-Me, 4-MeO and 4-1), but are absent in ortho-and Iri-(1: Y = 20,N) and (1: Y = 3-O2N). Instead, ortho-(1: Y = 2-O2N) exhibits intermolecular C-H center dot center dot center dot O(H) hydrogen bonds, while no intermolecular hydrogen bonds involving the OH group occur in either triclinic-(1: Y = 2-O2N) or (1: Y = 3-O2N). EI+-MS revealed the presence of olgomeric species, such as (nM + M')(+), where n is up to 4, and M' = H, Na or K.",
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T1 - 2-Hydroxyacetophenone arylhydrazones. Supramolecular arrangements based on C–H · · · O(H), CH · · · O(NO), N–H · · · O(H), N–H · · · O(NO), C–H · · · π or π · · · π interactions

AU - Baddeley, Thomas C.

AU - Franca, Luciana de Souza

AU - Howie, R. Alan

AU - de Lima, Geraldo M.

AU - Skakle, Jan

AU - de Souza, Jose Dias

AU - Wardell, James L.

AU - Wardell, Solange M. S. V.

PY - 2009/9

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N2 - Crystal structures, NMR and IR spectra and EI-MS+ of 2-hydroxyacetophenone arylhydrazones, 2-HOC6H4C(Me)=NNHC6H4Y (1: Y = 2-O2N, 3-O2N, 4-O2N, 4-Me, 4-MeO, H and 4-I) are reported. Two polymorphs of (1: Y = 2-O2N), triclinic and orthorhombic forms, have been identified. While strong intramolecular O-H center dot center dot center dot N(H) hydrogen bonds and layers of molecules are found for all solid 1, supramolecular arrangements of individual members are various and are derived from different combinations of intramolecular interactions, which include C-H center dot center dot center dot O(H), C-H center dot center dot center dot O(NO), N-H center dot center dot center dot O(H), N-H center dot center dot center dot O(NO) and C-H center dot center dot center dot pi hydrogen bonds, as well as pi center dot center dot center dot pi stacking interactions. Intermolecular N-H center dot center dot center dot O hydrogen-bonds involving the phenolic OH group are present in (1: Y = H, 4-O2N, 4-Me, 4-MeO and 4-1), but are absent in ortho-and Iri-(1: Y = 20,N) and (1: Y = 3-O2N). Instead, ortho-(1: Y = 2-O2N) exhibits intermolecular C-H center dot center dot center dot O(H) hydrogen bonds, while no intermolecular hydrogen bonds involving the OH group occur in either triclinic-(1: Y = 2-O2N) or (1: Y = 3-O2N). EI+-MS revealed the presence of olgomeric species, such as (nM + M')(+), where n is up to 4, and M' = H, Na or K.

AB - Crystal structures, NMR and IR spectra and EI-MS+ of 2-hydroxyacetophenone arylhydrazones, 2-HOC6H4C(Me)=NNHC6H4Y (1: Y = 2-O2N, 3-O2N, 4-O2N, 4-Me, 4-MeO, H and 4-I) are reported. Two polymorphs of (1: Y = 2-O2N), triclinic and orthorhombic forms, have been identified. While strong intramolecular O-H center dot center dot center dot N(H) hydrogen bonds and layers of molecules are found for all solid 1, supramolecular arrangements of individual members are various and are derived from different combinations of intramolecular interactions, which include C-H center dot center dot center dot O(H), C-H center dot center dot center dot O(NO), N-H center dot center dot center dot O(H), N-H center dot center dot center dot O(NO) and C-H center dot center dot center dot pi hydrogen bonds, as well as pi center dot center dot center dot pi stacking interactions. Intermolecular N-H center dot center dot center dot O hydrogen-bonds involving the phenolic OH group are present in (1: Y = H, 4-O2N, 4-Me, 4-MeO and 4-1), but are absent in ortho-and Iri-(1: Y = 20,N) and (1: Y = 3-O2N). Instead, ortho-(1: Y = 2-O2N) exhibits intermolecular C-H center dot center dot center dot O(H) hydrogen bonds, while no intermolecular hydrogen bonds involving the OH group occur in either triclinic-(1: Y = 2-O2N) or (1: Y = 3-O2N). EI+-MS revealed the presence of olgomeric species, such as (nM + M')(+), where n is up to 4, and M' = H, Na or K.

KW - arylhydrazones

KW - supramolecular arrangements

KW - hydrogen bonds

KW - hydrogen-bonded sheets

KW - rings

KW - 2,4-dinitrophenylhydrazone

KW - 4-nitrophenylhydrazone

KW - combination

KW - framework

KW - chains

U2 - 10.1524/zkri.2009.1121

DO - 10.1524/zkri.2009.1121

M3 - Article

VL - 224

SP - 213

EP - 224

JO - Zeitschrift für Kristallographie

JF - Zeitschrift für Kristallographie

SN - 0044-2968

IS - 4

ER -