Journal of Chemical Crystallography

, Volume 40, Issue 12, pp 1045–1048 | Cite as

Synthesis and Characterization of N,N-di(prop-2-ynyl)-p-toluidine

Original Paper
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Abstract

In order to investigate the intramolecular [4 + 2] cycloaddition, we prepared some new tertiary N-(5-substituted-2-furfuryl)-N-prop-2-ynyl-p-toluidines [Hergold-Brundić et al., Acta Cryst C56:e520, 2000; Mance and Jakopčić, Mol Divers 9:229, 2005; Mance, “unpublished results”] by the alkylation of secondary N-(5-substituted-2-furfuryl)-p-toluidines with the propargyl-bromide [Mance and Šindler-Kulyk, Synth Commun 26:923, 1996]. In the course of preparation of N-(5-methoxy-2-furfuryl)-N-prop-2-ynyl-p-toluidine [Mance, “unpublished results”], besides the main product (compound 1) (Scheme 1) we obtained N,N-di(prop-2-ynyl)-p-toluidine (compound 2) as the colourless crystals. The title compound 2, N,N-di(prop-2-ynyl)-p-toluidine, C13H13N, crystallizes in monoclinic C 2/c space group with unit cell parameters: a = 19.5319(9) Å, b = 7.5230(3) Å, c = 15.9000(7) Å, β = 112.554(5)°, V = 2157.64(18) Å3, Z = 8. The crystal structure is dominated by van der Waals forces only. The bond distances around amine N atom correspond to σ dominated bonds (1.467(2), 1.462(2) and 1.419(2) Å). The angles sum around amine N atom is in accord with sp3 hybridization (343°).

Graphical Abstract

The title compound is a by-product in the preparation of N-(5-methoxy-2-furfuryl)-N-prop-2-ynyl-p-toluidine and its crystal and molecular structure has been obtained by X-ray single crystal diffractometry method.

Keywords

Tertiary amines N, N-di(prop-2-ynyl)-p-toluidine Synthesis IR NMR and XRD 
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Notes

Acknowledgement

The Ministry of Science and Technology of the Republic of Croatia, Zagreb (Grant No. 0125012 and 098-1191344-2943) supported this work. G.P. gratefully acknowledges for diffraction time to record data to the scientific project 119-1193079-1332 under the framework of the scientific programme “Ligands, complexes, proteins-synthesis and structure-properties relationship”.

References

  1. 1.
    Mance AD, Borovička B, Jakopčić K, Pavlović G, Leban I (2002) J Heterocycl Chem 39:277; references cited thereinGoogle Scholar
  2. 2.
    Mance AD, unpublished resultsGoogle Scholar
  3. 3.
    Oxford Diffraction Ltd (2004) CrysAlis software (Version 1.171.26.). Abingdon, Oxfordshire OX14 4RX, UKGoogle Scholar
  4. 4.
    Sheldrick GM (2008) Acta Cryst A64:112CrossRefGoogle Scholar
  5. 5.
    Spek L (2003) J Appl Cryst 36:7CrossRefGoogle Scholar
  6. 6.
    Macrae CF, Bruno IJ, Chisholm, JA, Edgington, PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor, R, van de Streek JP, Wood A (2008) J Appl Crystallogr 41:466CrossRefGoogle Scholar
  7. 7.
    Hergold-Brundić A, Pavlović G, Mance AD, Jakopčić K (2000) Acta Cryst C56:e520Google Scholar
  8. 8.
    Mance AD, Jakopčić K (2005) Mol Divers 9:229CrossRefGoogle Scholar
  9. 9.
    Mance AD, Šindler-Kulyk M (1996) Synth Commun 26:923CrossRefGoogle Scholar
  10. 10.
    Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG (1987) J Chem Soc Perkin Trans II S1Google Scholar
  11. 11.
    Calabrese JC, McPhail A T, Sim GA (1970) J Chem Soc B:282Google Scholar
  12. 12.
    Steiner Th (1995) Z Kristallogr 210:459CrossRefGoogle Scholar
  13. 13.
    Steiner Th, Schreurs AMM, Kanters JA, Kroon J, van der Maas J, Lutz B (1997) J Mol Struct 436Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  1. 1.Department of Applied Chemistry, Faculty of Textile TechnologyUniversity of ZagrebZagrebCroatia
  2. 2.Faculty of Chemical Engineering and Technology, Department of Organic ChemistryUniversity of ZagrebZagrebCroatia

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