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Isolation and crystal structures of triethylenediamine-hydroquinone (1/1) and triethylenediamine-phenol (1/2)

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Abstract

Two crystalline adducts of triethylenediamine with hydroquinone [N(CH2CH2)3N·C6H4(OH)2,I] and phenol [N(CH2CH2)3N·2C6H5OH,II] have been isolated and characterized by X-ray analysis. ComplexI crystallizes in the monoclinic space groupC2/c, witha=11.944(2),b=9.491(2),c=11.986(2) Å,β=121.70(1)°, andZ=4. Both molecular components occupy sites of symmetry 2, and are linked alternately by N ⋯ H-O hydrogen bonds to form infinite zigzag chains. Crystals ofII are also monoclinic, with space groupP21/c,a=12.987(2),b=6.376(1),c=21.350(3) Å,β=106.94(1)°, andZ=4. The structure is composed of discrete hydrogen-bonded molecular aggregates corresponding to the stoichiometric formula. The triethylenediamine moieties in both adducts closely approximate to the idealizedD 3 h conformation. The structures have been refined toR values of 0.097 (I) and 0.092 (II) using, respectively, 479 and 1580 observed MoKα data.

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References

  • DeTitta, G. T., Edmond, J. W., Langs, D. A., and Hauptman, H. (1975)Acta Cryst. A 31, 472–479.

    Google Scholar 

  • Diamond, R. (1969)Acta Cryst. A 25, 43–55.

    Google Scholar 

  • Doedens, R. J. (1969) InCrystallographic Computing, F. R. Ahmed, ed. (Munksgaard, Copenhagen), pp. 198–199.

    Google Scholar 

  • Ermer, O., and Dunitz, J. D. (1969)Helv. Chim. Acta 52, 1861–1886.

    Google Scholar 

  • Farkas, A., and Mills, G. A. (1962)Adv. Catal. 13, 393–446.

    Google Scholar 

  • International Tables for X-Ray Crystallography (1974) Vol. IV (Kynoch Press, Birmingham), pp. 99, 149.

  • Jordan, T. H., and Mak, T. C. W. (1970)J. Chem. Phys. 52, 3790–3794.

    Google Scholar 

  • Lam, Y.-S., and Mak, T. C. W. (1978)Acta Cryst. B 34, 1915–1918.

    Google Scholar 

  • Mak, T. C. W., Tse, C.-S., Chong, Y.-H., and Mok, F.-C. (1977)Acta Cryst. B 33, 2980–2982.

    Google Scholar 

  • Mak, T. C. W., Lau, O. W., Ladd, M. F. C., and Povey, D. (1978a)Acta Cryst. B 34, 1290–1294.

    Google Scholar 

  • Mak, T. C. W., Yu, W.-H., and Lam, Y.-S. (1978b)Acta Cryst. B 34, 2061–2063.

    Google Scholar 

  • Mak, T. C. W., and Lam, Y.-S. (1978)Acta Cryst. B 34, 1732–1735.

    Google Scholar 

  • Mak, T. C. W. (1982)J. Chem. Soc., Perkin Trans. 2, 1435–1437.

    Google Scholar 

  • Nimmo, J. K., and Lucas, B. W. (1976)Acta Cryst. B 32, 348–353.

    Google Scholar 

  • Saunders, J. H., and Frisch, K. C. (1962)Polyurethanes: Chemistry and Technology, Part I (Interscience, New York).

    Google Scholar 

  • Schomaker, V., and Trueblood, K. N. (1968)Acta Cryst. B 24, 63–72.

    Google Scholar 

  • Sheldrick, G. M. (1982) InComputational Crystallography, D. Sayre, ed. (Oxford University Press, New York), pp. 506–514.

    Google Scholar 

  • Sparks, R. A. (1976) InCrystallographic Computing Techniques, F. R. Ahmed, ed. (Munksgaard, Copenhagen), pp. 452–467.

    Google Scholar 

  • Trotter, J., and Mak, T. C. W. (1979)Acta Cryst. B 35, 2367–2369.

    Google Scholar 

  • Tse, C.-S., Wong, Y.-S., and Mak, T. C. W. (1977)J. Appl. Cryst. 10, 68–69.

    Google Scholar 

  • Wallwork, S. C., and Powell, H. M. (1980)J. Chem. Soc., Perkin Trans. 2, 641–646.

    Google Scholar 

  • Yokozeki, A., and Kuchitsu, K. (1971)Bull. Chem. Soc. Jpn. 44, 72–77.

    Google Scholar 

  • Yu, P.-Y., and Mak, T. C. W. (1978)Acta Cryst. B 34, 3053–3056.

    Google Scholar 

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Mak, T.C.W., Yip, WH. & Book, L. Isolation and crystal structures of triethylenediamine-hydroquinone (1/1) and triethylenediamine-phenol (1/2). Journal of Crystallographic and Spectroscopic Research 14, 457–465 (1984). https://doi.org/10.1007/BF01160694

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