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Solvent-free synthesis and crystal structures of s-cis and s-trans N,N′-bis(2-hydroxycyclohexyl)ethane-1,2-diamine

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Abstract

The symmetrical amino alcohol synthesis via ring opening of cyclohexene oxide with ethylendiamine is illustrated by synthesis and characterization of β-amino alcohols s-cis-(SSSS)-cy2en (1) and s-trans-(SSRR)-cy2en (2) (cy2en = N,N′-bis(2-hydroxycyclohexyl)ethane-1,2-diamine) in one step and with high yield. The reaction was carried out in a microwave reactor under solvent-free conditions. These products were characterized by IR and Raman spectroscopy, elemental analysis, thermal methods (TGA, DTG and DTA), mass spectrometry and 1H and 13C NMR spectroscopy. The crystal structures of 1 and 2 were determined by single crystal X-ray structural analysis, followed by DFT calculations. Intramolecular hydrogen bond was observed in 1 with C 2 symmetry, but not in 2 with C i symmetry. The nature of intramolecular hydrogen bond in 1 has been investigated by AIM and NBO analyses. The molecules in 1 are linked into an infinite chain along the [001] direction, giving rise to R 44 (8) graph-set motif, while the molecules in 2 are linked into a 2D network in the bc plane, giving rise to R 22 (10) and R 33 (12) motifs. The protonation equilibria of 1 and 2 have been studied by pH-potentiometry, with pK 1 9.01 and pK 2 5.50 determined for 1 and pK 1 8.58 and pK 2 5.26 determined for 2.

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References

  1. Ojima I (ed) (1996) Enantioselective synthesis of β-amino acids. VCD Publishers, New York (and references cited therein)

  2. Cole DC (1994) Tetrahedron 50:9517

    Article  CAS  Google Scholar 

  3. Juraristi E, Quintana D, Escalante J (1994) Aldrichim Acta 27:3

    Google Scholar 

  4. Cardillo G, Tomasini C (1996) Chem Soc Rev 25:117

    Article  CAS  Google Scholar 

  5. Ager DJ, Prakash I, Schaad DR (1996) Chem Rev 96:835

    Article  CAS  Google Scholar 

  6. Bergmeier SC (2000) Tetrahedron 56:2561

    Article  CAS  Google Scholar 

  7. Chini M, Crotti P, Macchia F (1991) J Org Chem 56:5939

    Article  CAS  Google Scholar 

  8. Huerta G, Contreras-Ordoñez G, Alvarez-Toledano C, Santes V, Gomez E, Toscano RA (2004) Synth Commun 34:2393

    Article  CAS  Google Scholar 

  9. Deyrup JA, Moyer CL (1969) J Org Chem 34:175

    Article  CAS  Google Scholar 

  10. Chini M, Crotti P, Macchia F (1990) Tetrahedron Lett 31:4661

    Article  CAS  Google Scholar 

  11. Chandrasekhar S, Ramachandar S, Prakash JS (2000) Synthesis 13:1817

    Article  Google Scholar 

  12. Reddy LR, Reddy MA, Bhanumathi N, Rao KR (2001) Synthesis 6:831

    Article  Google Scholar 

  13. Sekar G, Singh VK (1999) J Org Chem 64:287

    Article  CAS  Google Scholar 

  14. Chandrasekhar S, Reddy CR, Babu BN, Chandrasekhar G (2002) Tetrahedron Lett 43:3801

    Article  CAS  Google Scholar 

  15. Currini M, Epifano F, Marcotullio MC, Rosati O (2001) Eur J Org Chem 21:4149

    Article  Google Scholar 

  16. Napitupulu M, Griggs BL, Luo S-X, Turner P, Maeder M, Lawrance GA (2009) J Heterocycl Chem 46:243

    Article  CAS  Google Scholar 

  17. Caddick S (1995) Tetrahedron 51:10403

    Article  CAS  Google Scholar 

  18. Maeder M, Neuhold YM (2007) Practical data analysis in chemistry. Elsevier, Amsterdam

    Google Scholar 

  19. Takacs-Novak K, Tam KY (2001) Anal Chim Acta 434:157

    Article  Google Scholar 

  20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stramann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci BP, Omelli C, Adamo C, Cliford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Ai-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill B, Johson PMW, Chen W, Johson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) GAUSSIAN 98, Revision A.7, Gaussian Inc., Pittsburgh, PA

  21. Becke ADJ (1993) Chem Phys 98:5648

    CAS  Google Scholar 

  22. Biegler-Koenig FW, Schonbohm J, Bayles D (2001) J Comput Chem 22:545

    Article  Google Scholar 

  23. Oxford Diffraction (2009) CrysAlisPro, version 171.33.53. Oxford Diffraction Ltd, Abingdon

    Google Scholar 

  24. Sheldrick GM (2008) Acta Crystallogr A64:112

    CAS  Google Scholar 

  25. Spek AL (2003) J Appl Crystallogr 36:7

    Article  CAS  Google Scholar 

  26. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

  27. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood JPA (2008) J Appl Crystallogr 41:466

    Article  CAS  Google Scholar 

  28. Gustafson RL, Martell AE (1959) J Am Chem Soc 81:525

    Article  CAS  Google Scholar 

  29. Bhattacharyya RG, Paul AB, Chatterjee AB, Bag SP (1990) Indian J Chem 29A:986

    CAS  Google Scholar 

  30. Allen H, Kennard O, Watson DG, Brammer L, Orpen AG (1987) J Chem Soc Perkin Trans II:S1

    Google Scholar 

  31. de Sousa AS, Hlam Z, Fernandes MA, Marques HM (2010) Acta Crystallogr C66:o553

    Google Scholar 

  32. Lechner B-D, Merzweiler K (2010) Acta Crystallogr E66:o122

    CAS  Google Scholar 

  33. Etter MC, MacDonald JC, Bernstein J (1990) Acta Crystallogr B46:256

    CAS  Google Scholar 

  34. Allen FH (2002) Acta Crystallogr B58:380

    CAS  Google Scholar 

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Acknowledgments

This research was supported by Payame Noor University of Tehran, Iran.

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Authors and Affiliations

  1. Chemistry Department, Payame Noor University, 19395-4697, Tehran, Iran

    Mohammad Hakimi & Leila Pouyanmehr

  2. Laboratory of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000, Zagreb, Croatia

    Boris-Marko Kukovec

  3. Chemistry Department, Birjand University, 13179, Birjand, South Khorasan, Iran

    Heidar Raissi

  4. Fachbereich C—Anorganische Chemie, Bergische Universität Wuppertal, 42119, Wuppertal, Germany

    Fabian Mohr & Esther Schuh

Authors
  1. Mohammad Hakimi
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  2. Boris-Marko Kukovec
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  3. Heidar Raissi
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  4. Leila Pouyanmehr
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  5. Fabian Mohr
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  6. Esther Schuh
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Correspondence to Mohammad Hakimi or Boris-Marko Kukovec.

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Hakimi, M., Kukovec, BM., Raissi, H. et al. Solvent-free synthesis and crystal structures of s-cis and s-trans N,N′-bis(2-hydroxycyclohexyl)ethane-1,2-diamine. Struct Chem 24, 81–88 (2013). https://doi.org/10.1007/s11224-012-0017-z

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  • DOI: https://doi.org/10.1007/s11224-012-0017-z

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