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X-ray crystal structure conformational studies on r-4,c-6-dimethyl-1,3- dithian and its oxides, r-4,c-6-dimethyl-1,3-dithian t-1-oxide, and r-4,c-6-dimethyl-1,3-dithian t-1,t-3-dioxide

Publication ,  Journal Article
McPhail, AT; Onan, KD; Koskimies, J
Published in: Journal of the Chemical Society, Perkin Transactions 2
January 1, 1976

The crystal structures of the title compounds [the 1,3-dithian (I), and its oxides (II) and (III)] have been determined from X-ray diffractometer data. Monoclinic crystals of (I) and (II) are isomorphous, space group C2/c. with for (I) : a = 20.08(1), b = 5.71(1), c = 15.69(1) Å, β = 118.4(1)°: and for (II) : a = 20.33(1), b = 5.68(1), c = 16.11(1) Å, β = 119.0(1)°. Crystals of (III) are also monoclinic, space group P2 1/c, with a = 5.49(1), b = 15.52(1), c = 10.81(1) Å, β = 105.9(1)°. The structures were solved by the heavy-atom method and atomic parameters were refined by full-matrix least-squares calculations to R 0.047 (I), 0.044 (II), and 0.072 (III) over 1 129, 1 594, and 1 241 statistically significant reflections. In all three molecules the dithian rings adopt chair conformations which are increasingly more puckered as the number of substituents increases. The C-S distances in (I) and (II) reveal interesting differences which depend upon the degree of substitution at the carbon atoms.

Duke Scholars

Published In

Journal of the Chemical Society, Perkin Transactions 2

DOI

ISSN

1472-779X

Publication Date

January 1, 1976

Issue

9

Start / End Page

1004 / 1008

Related Subject Headings

  • Organic Chemistry
 

Citation

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McPhail, A. T., Onan, K. D., & Koskimies, J. (1976). X-ray crystal structure conformational studies on r-4,c-6-dimethyl-1,3- dithian and its oxides, r-4,c-6-dimethyl-1,3-dithian t-1-oxide, and r-4,c-6-dimethyl-1,3-dithian t-1,t-3-dioxide. Journal of the Chemical Society, Perkin Transactions 2, (9), 1004–1008. https://doi.org/10.1039/P29760001004
McPhail, A. T., K. D. Onan, and J. Koskimies. “X-ray crystal structure conformational studies on r-4,c-6-dimethyl-1,3- dithian and its oxides, r-4,c-6-dimethyl-1,3-dithian t-1-oxide, and r-4,c-6-dimethyl-1,3-dithian t-1,t-3-dioxide.” Journal of the Chemical Society, Perkin Transactions 2, no. 9 (January 1, 1976): 1004–8. https://doi.org/10.1039/P29760001004.
McPhail, A. T., et al. “X-ray crystal structure conformational studies on r-4,c-6-dimethyl-1,3- dithian and its oxides, r-4,c-6-dimethyl-1,3-dithian t-1-oxide, and r-4,c-6-dimethyl-1,3-dithian t-1,t-3-dioxide.” Journal of the Chemical Society, Perkin Transactions 2, no. 9, Jan. 1976, pp. 1004–08. Scopus, doi:10.1039/P29760001004.

Published In

Journal of the Chemical Society, Perkin Transactions 2

DOI

ISSN

1472-779X

Publication Date

January 1, 1976

Issue

9

Start / End Page

1004 / 1008

Related Subject Headings

  • Organic Chemistry