Crystal Structure of Tetrahymanol Hemihydrate

David A. Langs, William L. Duax, H. L. Carrell, Helen Berman, Eliahu Caspi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The crystal structure of a hemihydrate of the pentacyclic triterpenoid tetrahymanol, C30H52O·1/2H2O [monoclinic, P21, a = 7.417 (1) Å, b = 11.438 (2), c = 30.248 (4), β = 91.95°, Z = 4,R = 0.076] has been determined. Steric overcrowding warps the gross conformation of the two molecules in the asymmetric unit and generates unusually long carbon-carbon single bonds. The observed weakening of the C8–C14 bond, whose average length is 1.61 Å, is consistent with its scission observed in mass spectral experiments. Although the molecular skeleton possesses rotational symmetry, the observed conformations are markedly asymmetric, appear to be independent of the hydroxyl moiety, and suggest the presence of conformational isomers in solution.

Original languageEnglish (US)
Pages (from-to)2134-2137
Number of pages4
JournalJournal of Organic Chemistry
Volume42
Issue number12
DOIs
StatePublished - Jun 1 1977
Externally publishedYes

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Conformations
Carbon
Crystal structure
Isomers
Hydroxyl Radical
Molecules
Experiments
tetrahymanol
single bond

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Langs, D. A., Duax, W. L., Carrell, H. L., Berman, H., & Caspi, E. (1977). Crystal Structure of Tetrahymanol Hemihydrate. Journal of Organic Chemistry, 42(12), 2134-2137. https://doi.org/10.1021/jo00432a025
Langs, David A. ; Duax, William L. ; Carrell, H. L. ; Berman, Helen ; Caspi, Eliahu. / Crystal Structure of Tetrahymanol Hemihydrate. In: Journal of Organic Chemistry. 1977 ; Vol. 42, No. 12. pp. 2134-2137.
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Langs, DA, Duax, WL, Carrell, HL, Berman, H & Caspi, E 1977, 'Crystal Structure of Tetrahymanol Hemihydrate', Journal of Organic Chemistry, vol. 42, no. 12, pp. 2134-2137. https://doi.org/10.1021/jo00432a025

Crystal Structure of Tetrahymanol Hemihydrate. / Langs, David A.; Duax, William L.; Carrell, H. L.; Berman, Helen; Caspi, Eliahu.

In: Journal of Organic Chemistry, Vol. 42, No. 12, 01.06.1977, p. 2134-2137.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Crystal Structure of Tetrahymanol Hemihydrate

AU - Langs, David A.

AU - Duax, William L.

AU - Carrell, H. L.

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AU - Caspi, Eliahu

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AB - The crystal structure of a hemihydrate of the pentacyclic triterpenoid tetrahymanol, C30H52O·1/2H2O [monoclinic, P21, a = 7.417 (1) Å, b = 11.438 (2), c = 30.248 (4), β = 91.95°, Z = 4,R = 0.076] has been determined. Steric overcrowding warps the gross conformation of the two molecules in the asymmetric unit and generates unusually long carbon-carbon single bonds. The observed weakening of the C8–C14 bond, whose average length is 1.61 Å, is consistent with its scission observed in mass spectral experiments. Although the molecular skeleton possesses rotational symmetry, the observed conformations are markedly asymmetric, appear to be independent of the hydroxyl moiety, and suggest the presence of conformational isomers in solution.

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