N,N'-Bis-(2-methoxybenzylidene) adducts of 1,2-ethanediamine, 1,3-propanediamine and 1,4-butanediamine

J. Reglinski, M.K. Taylor, A.R. Kennedy

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

We have isolated and crystallographically characterized the three homologous compounds N,N'-bis(2-methoxy­benzyl­idene)­ethane-1,2-di­amine (MeSalen), C18H20N2O2, N,N'-bis(2-methoxy­benzyl­idene)­propane-1,3-di­amine (MeSalpr), C19H22N2O2, and N,N'-bis(2-methoxy­benzyl­idene)­butane-1,4-di­amine (MeSalbu), C20H24N2O2. In contrast with MeSalpr, the mol­ecules of MeSalen and MeSalbu, which have an even number of methyl­ene units, have crystallographic symmetry. Comparing these methoxy-substituted species with their hydroxy equivalents shows that the aryl rings rotate upon removal of the O - HN hydrogen bonds. The packing of MeSalen and MeSalpr is controlled by C - Hπ interactions, whereas that of MeSalbu has only van der Waals contacts.
LanguageEnglish
Pageso169-o172
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume60
Issue number3
DOIs
Publication statusPublished - 10 Feb 2004

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ethylenediamine
Putrescine
Amines
Propane
Ethane
Hydrogen
Hydrogen bonds
trimethylenediamine

Keywords

  • isolated
  • crystallographically characterized
  • homologous compounds
  • MeSalpr
  • MeSalbu
  • MeSalen
  • methyl­ene units
  • hydroxy equivalents
  • hydrogen bonds

Cite this

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title = "N,N'-Bis-(2-methoxybenzylidene) adducts of 1,2-ethanediamine, 1,3-propanediamine and 1,4-butanediamine",
abstract = "We have isolated and crystallographically characterized the three homologous compounds N,N'-bis(2-methoxy­benzyl­idene)­ethane-1,2-di­amine (MeSalen), C18H20N2O2, N,N'-bis(2-methoxy­benzyl­idene)­propane-1,3-di­amine (MeSalpr), C19H22N2O2, and N,N'-bis(2-methoxy­benzyl­idene)­butane-1,4-di­amine (MeSalbu), C20H24N2O2. In contrast with MeSalpr, the mol­ecules of MeSalen and MeSalbu, which have an even number of methyl­ene units, have crystallographic symmetry. Comparing these methoxy-substituted species with their hydroxy equivalents shows that the aryl rings rotate upon removal of the O - HN hydrogen bonds. The packing of MeSalen and MeSalpr is controlled by C - Hπ interactions, whereas that of MeSalbu has only van der Waals contacts.",
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N,N'-Bis-(2-methoxybenzylidene) adducts of 1,2-ethanediamine, 1,3-propanediamine and 1,4-butanediamine. / Reglinski, J.; Taylor, M.K.; Kennedy, A.R.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 60, No. 3, 10.02.2004, p. o169-o172.

Research output: Contribution to journalArticle

TY - JOUR

T1 - N,N'-Bis-(2-methoxybenzylidene) adducts of 1,2-ethanediamine, 1,3-propanediamine and 1,4-butanediamine

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N2 - We have isolated and crystallographically characterized the three homologous compounds N,N'-bis(2-methoxy­benzyl­idene)­ethane-1,2-di­amine (MeSalen), C18H20N2O2, N,N'-bis(2-methoxy­benzyl­idene)­propane-1,3-di­amine (MeSalpr), C19H22N2O2, and N,N'-bis(2-methoxy­benzyl­idene)­butane-1,4-di­amine (MeSalbu), C20H24N2O2. In contrast with MeSalpr, the mol­ecules of MeSalen and MeSalbu, which have an even number of methyl­ene units, have crystallographic symmetry. Comparing these methoxy-substituted species with their hydroxy equivalents shows that the aryl rings rotate upon removal of the O - HN hydrogen bonds. The packing of MeSalen and MeSalpr is controlled by C - Hπ interactions, whereas that of MeSalbu has only van der Waals contacts.

AB - We have isolated and crystallographically characterized the three homologous compounds N,N'-bis(2-methoxy­benzyl­idene)­ethane-1,2-di­amine (MeSalen), C18H20N2O2, N,N'-bis(2-methoxy­benzyl­idene)­propane-1,3-di­amine (MeSalpr), C19H22N2O2, and N,N'-bis(2-methoxy­benzyl­idene)­butane-1,4-di­amine (MeSalbu), C20H24N2O2. In contrast with MeSalpr, the mol­ecules of MeSalen and MeSalbu, which have an even number of methyl­ene units, have crystallographic symmetry. Comparing these methoxy-substituted species with their hydroxy equivalents shows that the aryl rings rotate upon removal of the O - HN hydrogen bonds. The packing of MeSalen and MeSalpr is controlled by C - Hπ interactions, whereas that of MeSalbu has only van der Waals contacts.

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KW - MeSalbu

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KW - methyl­ene units

KW - hydroxy equivalents

KW - hydrogen bonds

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