Structures of E- and Z-isomers of 1-methyl-5-[(2,4,6-trimethylphenyl)methylene]imidazolidine-2,4-dione

Drew, Michael G. B.; Mok, K. F.; Ang, K. P.; Tan, S. F.

doi:10.1107/s0108270187093399

Acta Crystallogr C

1987

DOI: 10.1107/s0108270187093399

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Structures of E- and Z-isomers of 1-methyl-5-[(2,4,6-trimethylphenyl)methylene]imidazolidine-2,4-dione

Michael G. B. Drew¹,

K. F. Mok²,

K. P. Ang³

et al.

Abstract: Abstract. CI4HI6N202, M r= 244.30, monoclinic, P2Jc, for both isomers. E-isomer: a=8.203 (7), b=8-278(7), c=18.939 (9) Owing to the presence of methyl groups in the ortho positions of the benzene ring, the plane of this ring is rotated away from that of the imidazolidine-2,4-dione ring but the angle of rotation is smaller in the case of the E-isomer at 57.1 (3) ° than in the case of the Z-isomer in which the two planes are almost perpendicular at 84.2 (3) ° .

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NMR spectroscopic study of configurations and conformations of 5‐pyridylmethylenehydantoins

Tan

Ang

How

1990

J of Physical Organic Chem

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Nine 5‐pyridylmethylenehydantoins were prepared. Each of the 1‐methyl‐substitute compounds was obtained in two stereoisomeric forms. Only one form of each of the 3‐methyl‐substituted and N‐unsubstituted compounds was obtained directly from synthesis but could be partially converted into the other stereoisomer photochemically. The Z/E configurations and the conformational relationship between the pyridine and hydantoin rings were studied by 1H and 13C NMR spectroscopy, including variable‐temperature 1H NMR. The existence of NH…︁N or CH…︁N interactions and the possibility of tautomerism are suggested for some of the compounds. The Z‐isomers of compounds with 2‐ or 3‐pyridyl rings prefer an s‐cis conformation whereas the E‐isomers prefer an s‐trans conformation.

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NMR spectroscopic study of configurations and conformations of 5‐pyridylmethylenehydantoins

Tan

Ang

How

1990

J of Physical Organic Chem

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The structure of hydantoins in solution and in the solid state

Kleinpeter

1997

Struct Chem

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The results of NMR spectroscopic and X-ray crystallographic studies are critically discussed with respect to the structure of hydantoins, their tautomerism, and their acidity. The imide NH proton of the preferred, nearly planar 2,4-imidazolidine-dione tautomer proved to be more acidic than the corresponding amide NH proton. Phenyl substituents at the ring nitrogen atoms and at C-5 are twisted from the plane of the hydantoin ring; in case of ortho substituents restricted rotation about the N-aryl bond was found and the barrier to rotation determined by dynamic NMR spectroscopy.For 5-benzyl substituents, a folded conformation of the two rings, due to intramolecular interactions, was found and for 5-exo-methylene substituted hydantoins the relevant E/Z isomerism at the exo-cyclic C, C double bond was studied. In addition, the IH and 13C chemical shifts of the hydantoins proved to excellently indicate the electronic distribution along the hydantoin ring moiety. Finally, the mass spectrometric fragmentation of the hydantoins is critically discussed.

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Methylmercury and dimethylthallium complexes of 5-(4′-dimethylaminobenzylidene)-2-thiohydantoin (HDABTd)

et al. 1999

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Structures of E- and Z-isomers of 1-methyl-5-[(2,4,6-trimethylphenyl)methylene]imidazolidine-2,4-dione

Cited by 3 publications

References 1 publication

NMR spectroscopic study of configurations and conformations of 5‐pyridylmethylenehydantoins

NMR spectroscopic study of configurations and conformations of 5‐pyridylmethylenehydantoins

The structure of hydantoins in solution and in the solid state

Methylmercury and dimethylthallium complexes of 5-(4′-dimethylaminobenzylidene)-2-thiohydantoin (HDABTd)

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