Stereochemistry of Benzanilides and N-Methylbenzanilides
Bibliographic Information
- Other Title
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- ベンズアニリド及びN-メチルベンズアニリドの立体化学
- ベンズアニリド オヨビ N メチルベンズアニリド ノ リッタイ カガク
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Abstract
Conformations of benzanilide (1), N-methylbenzanilide (2) and those with a methyl group (s) ortho to the amide bond (11-16, 21-26) in solution and in the crystal have been studied. N-Methylbenzanilide (2) exists in cis-amide (E) form in the crystal. In CDCl3 solution, cis-amide form is also predominant (99%), while benzanilide (1) exists in trans-amide (Z) form in the crystal and in solution. In the crystal, all the methyl-substituted benzanilides (11-16) exist in trans-amide conformation and the introduction of an ortho-methyl group (s) makes the interplanar angles of the aromatic rings and the amide group (Ar-amide) larger. N-Methylbenzanilides (21-25) exist in cis form in the crystal except the compound (26) which has four methyl groups ortho to the amide bond. For the N-methylbenzanilides, the effects of introduction of one or two ortho-methyl groups on the dihedral angles of Ar-amide are smaller than that for the secondary benzanilides. In solution, benzanilides (11-16) exist exclusively in trans conformation except for the compound 12 which has a minor cis conformer (3%) in CDCl3, whereas N-methylbenzanilides (21-25) exist in equilibrium between the major cis-form and the minor trans-form. The tetramethyl derivative (26) exists in trans conformation in solution as observed in the crystal. For N-methyl-benzanilides, an introduction of a methyl group (s) ortho to the amide bond seems to destabilize the cis-amide conformation in solution, resulting in an increased ratio of the trans-amide conformation.
Journal
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- YAKUGAKU ZASSHI
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YAKUGAKU ZASSHI 114 (6), 414-430, 1994
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001206155458816
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- NII Article ID
- 110003649503
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- NII Book ID
- AN00284903
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- ISSN
- 13475231
- 00316903
- http://id.crossref.org/issn/00316903
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- NDL BIB ID
- 3885946
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed