Interplay of hydrogen bonds, iodo...nitro interactions and aromatic p...p stacking interactions in iodo-nitroanilines

S. J. Garden, S. P. Fontes, J. L. Wardell, Janet Mabel Scott Skakle, C. Glidewell

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Molecules of 2-iodo-5-nitroaniline (I) are linked by N-H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic pi...pi stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo ... nitro interactions into sheets of two types, each containing only a single type of molecule: pi...pi stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N-H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic pi...pi stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

Original languageEnglish
Pages (from-to)701-709
Number of pages8
JournalActa Crystallographica Section B, Structural Science
VolumeB58
DOIs
Publication statusPublished - 2002

Keywords

  • C-METHYLATED NITROANILINES
  • CRYSTAL-STRUCTURES
  • MOLECULES
  • 1,4-DIIODOBENZENE
  • DIFFRACTION
  • COMPLEXES
  • PATTERNS
  • ACID

Cite this

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic p...p stacking interactions in iodo-nitroanilines. / Garden, S. J.; Fontes, S. P.; Wardell, J. L.; Skakle, Janet Mabel Scott; Glidewell, C.

In: Acta Crystallographica Section B, Structural Science, Vol. B58, 2002, p. 701-709.

Research output: Contribution to journalArticle

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AU - Fontes, S. P.

AU - Wardell, J. L.

AU - Skakle, Janet Mabel Scott

AU - Glidewell, C.

PY - 2002

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N2 - Molecules of 2-iodo-5-nitroaniline (I) are linked by N-H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic pi...pi stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo ... nitro interactions into sheets of two types, each containing only a single type of molecule: pi...pi stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N-H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic pi...pi stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

AB - Molecules of 2-iodo-5-nitroaniline (I) are linked by N-H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic pi...pi stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo ... nitro interactions into sheets of two types, each containing only a single type of molecule: pi...pi stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N-H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic pi...pi stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

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KW - COMPLEXES

KW - PATTERNS

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