Skip to main content
SpringerLink
Log in

X-ray crystal structure of 2-hydroxy-2′-(1,4-bisoxo-6-hexanol)-1,1′-biphenyl

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The X-ray crystal structure of 2-hydroxy-2′-(1,4-bisoxo-6-hexanol)-1,1′-biphenyl, 3, is presented. This molecule crystallizes in the monoclinic space group P21/n (a = 9.440(2), b = 12.679(3), c = 11.679(3) Å β = 94.60(2)° V = 1382.5(5) Å3; Z = 4). One of the unique features of the X-ray structure of 3 is the intramolecular hydrogen bonding. The hydrogens of the phenolic and hydroxy groups occupies bridging positions via hydrogen bonding to an ether oxygen (O1) and a phenolic oxygen (O4), respectively. This hydrogen bonding does not affect the interplanar angle between phenyl rings (49.34°), which is in the range expected for ortho-disubstituted biphenyl compounds. The hydrogen bonding of this type explains why it is difficult to alkylate both phenoxy groups of 2,2′-biphenol with tetrahydropyranyl protected 2-(2′-chloroethoxy)ethanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Pedersen, C.J.; J. Am. Chem. Soc. 1967, 89, 2495

    Google Scholar 

  2. Pedersen, C.J.; ibid 1967, 89, 7017.

    Google Scholar 

  3. Reinhoudt, D.N.; De Jong, F.; Van De Vondervoort, E.M.; Tetrahedron 1981, 37, 1753.

    Google Scholar 

  4. Bartsch B.A.; Czech B.; Czech, A.; Heterocyclic Chem. 1994, 21, 341.

    Google Scholar 

  5. Kyba E.P.; Helgeson R.C.; Madar, K.; Gokel G.W.; Tarnowski T.L.; Moore S.S.; Cram D.J.; J. Am. Chem. Soc. 1977 95, 2564.

    Google Scholar 

  6. Lin, W.O.; da Costa J.B.N.; Alt H.G.; Rogers R.D.; Z. Naturforsch. Teil B 1989 44, 1331.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, The University of Alabama at Birmingham, 901 South 14th Street, Room 201, Birmingham, Alabama, 35294-1240

    Maheswaran Hariharasarma & Gary M. Gray

Authors
  1. Maheswaran Hariharasarma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gary M. Gray
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hariharasarma, M., Gray, G.M. X-ray crystal structure of 2-hydroxy-2′-(1,4-bisoxo-6-hexanol)-1,1′-biphenyl. Journal of Chemical Crystallography 28, 297–301 (1998). https://doi.org/10.1023/A:1021805404077

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1021805404077

Search

Navigation