Skip to main content
SpringerLink
Log in

Dielectric and conductivity studies of stereo-selectively synthesized d- and l-nor-ephedrine

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

The stereo isomers, d- and l-phenyl propanolamine hydrochloride (nor-ephedrine) were stereo-selectively synthesized from benzaldehyde and nitroethane followed by catalytic reduction using hydrogen and Raney nickel. The nor-ephedrine was characterized by UV, IR, and LC/MS analysis. The purity of the synthesized nor-ephedrine hydrochlorides was analyzed using HPLC. Resolution of d- and l-isomer of PPA hydrochloride was carried out using the resolving agent, d-3-formyl-2,2,5,5-tetramethyl-1,3-thiazolidine-4-carboxylicacid. Optical rotation was found to be ±36°. The temperature and frequency dependence of dielectric constant, dielectric loss, and conductivity of d- and l-isomers of nor-ephedrine were studied over a range of frequency (50 Hz–5 MHz) and temperature (40–140 °C). It was found that d-isomer possesses higher dielectric constant and AC conductivity values compared to l-isomer. The band gap of 1.35 and 1.69 eV for d- and l-isomers, respectively, indicates that these two compounds behave as organic semiconductor materials.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18

Similar content being viewed by others

References

  1. Nogradi M. Stereoselective synthesis: a practical approach. 2nd ed. New York: Wiley-VCH; 1995.

    Google Scholar 

  2. Bhushan R, Martens J, Arora M. Direct resolution of \((\pm )\)-ephedrine and atropine into their enantiomers by impregnated TLC. Biomed Chromatogr. 2001;15:151–4.

    Article  CAS  Google Scholar 

  3. Drew CD, Knight GT, Hughes DT, Bush M. Comparison of the effects of d-(-)-ephedrine and l-(+)-pseudoephedrine on the cardiovascular and respiratory systems in man. J Clin Pharmacol. 1978;6:221–5.

    Article  CAS  Google Scholar 

  4. Wilen SH, Collet A, Jacques J. Strategies in optical resolutions. Tetrahedron. 1976;33:2725–36.

    Article  Google Scholar 

  5. Shao G, Wu F, Wang DS, Zhu R, Luo X. Quantitative analysis of l-ephedrine and d-pseudoephedrine in plasma by high-performance liquid chromatography with fluorescence detection. Acta Pharm Sin. 1995;30:384–9.

    CAS  Google Scholar 

  6. Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S. The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? Anesth Analg. 2003;97:1239–45.

    Article  CAS  Google Scholar 

  7. Jonscher AK. The universal dielectric response. Nature. 1977;267:673–9.

    Article  CAS  Google Scholar 

  8. Porta M, Zumeta E. Implementing the Stockholm treaty on persistent organic pollutants. Occup Environ Med. 2002;59:651–2.

    Article  CAS  Google Scholar 

  9. Health effects of PCBs. http://www.epa.gov/epawaste/hazard/tsd/pcbs/pubs/effects.htm. Accessed 02 Nov 2013.

  10. Manske RHF, Johnson TB. Synthesis of ephedrine and structurally similar compounds. I. A new synthesis of ephedrine. J Org Chem. 1929;51:580–2.

    CAS  Google Scholar 

  11. Hoover FW, Hass HB. Synthesis of 2-amino-1-phenyl-1-propanol and its methylated derivatives. J Org Chem. 1947;12:506–9.

    Article  CAS  Google Scholar 

  12. Jonas K. Synthesis of (1r*,2s*)-1-phenyl-2-nitropropanol. European Patent 960,876.

  13. Lee HK, Kang S, Choi EB. Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution. J Org Chem. 2013;77:5454–60.

    Article  Google Scholar 

  14. Bhagavannarayana G, Ananthamurthy RV, Budakoti GC, Kumar B, Bartwal KS. A study of the effect of annealing on fe-doped LiNbO\(_3\) by HRXRD, XRT FT-IR. J Appl Crystallogr. 2005;38:768–71.

    Article  CAS  Google Scholar 

  15. Dyer JR. Applications of absorption spectroscopy of organic compounds. New Delhi: Prentice Hall of India; 1989.

    Google Scholar 

  16. Nakamoto K. Infrared and Raman Spectra of inorganic and coordination compounds. 3rd ed. Hoboken: Wiley; 1978.

    Google Scholar 

  17. Boomadevi S, Mittal HP, Dhansekaran R. Synthesis, crystal growth characterization of 3-methyl 4-nitropyridine 1-oxide (POM) single crystals. Cryst Growth. 2004;261:55–62.

    Article  CAS  Google Scholar 

  18. Meena M, Mahadevan CK. Growth and electrical characterization of l-arginine added KDP and ADP single crystals. Cryst Res Technol. 2008;43:166–72.

    Article  CAS  Google Scholar 

  19. Kanagathara N, Anbalagan G. Growth, optical and dielectric studies on pure and l-Lysine doped KDP crystals. Int J Optics. 2012;2012:6.

    Article  Google Scholar 

  20. Binitha MP, Pradyumnan PP. Thermal degradation, dielectric and magnetic studies on copper tartrate trihydrate crystals. J Therm Anal Calorim. 2013;114:665–9.

    Article  CAS  Google Scholar 

  21. Suresh S, Ramanand A, Jayaraman D, Mani P, Anand K. Growth, optical, theoretical and dielectric studies on l-valine single crystals. Int J ChemTech Res. 2011;13:122–5.

    Google Scholar 

  22. Ortiz RP, Facchetti A, Marks TJ. High-k organic, inorganic, and hybrid dielectrics for low-voltage organic field-effect transistors. Chem Rev. 2010;110:205–39.

    Article  CAS  Google Scholar 

  23. Hu X, Wang Z, Gao B, Shi Z, Kan H, Luo X, Tao W. Equivalent conductivity and its activation energy of \(\text{ NaF-AlF }_3\) melts. Trans Nonferr Metal Soc. 2009;19:719–23.

    Article  CAS  Google Scholar 

  24. Mahamoud H, Louati B, Hlel F, Guidara K. Conductivity and dielectric studies on \((\text{Na}_{0.4}\,\text{Ag}_{0.6})_2\,\text{PbP}_2\text{O}_7\) compound. Bull Mater Sci. 2011;34:1069–75.

    Article  CAS  Google Scholar 

  25. Rais D, Hain J, Pich A, Pochekailov S, Nespurek S, Adler HJP, Smacek A, Reboun J. Electrical conductivity in thin films fabricated from nanoparticles of a polymeric composite based on PEDOT. Mat Sci. 2009;27:769–80.

    CAS  Google Scholar 

  26. Indris S, Heitjans P, Ulrich M, Bunde A. AC and DC conductivity in nano and microcrystalline \(\text{Li}_2\text{O}\) a \(\text{B}_2\text{O}_3\) composites: experimental results and theoretical models. Phys Chem. 2005;219:89–103.

    CAS  Google Scholar 

  27. Vzquez H, Gao W, Flores F, Kahn A. Energy level alignment at organic heterojunctions: role of the charge neutrality level. Phys Rev B. 2005;71:1–4.

    Google Scholar 

  28. Stadler P, Track AM, Ullah M, Sitter H, Matt GJ, Koller G, Singh TB, Neugebauer H, Sariciftci NS, Ramsey MG. The role of the dielectric interface in organic transistors: a combined device and photoemission study. Org Electron. 2010;11:207–11.

    Article  CAS  Google Scholar 

  29. Greiner MT, Helander MG, Tang WM, Wang ZB, Qiu J, Lu ZH. Universal energy-level alignment of molecules on metal oxides. Nat Mater. 2012;11:76–81.

    Article  CAS  Google Scholar 

  30. Niu Y, Bai Y, Yu K, He L, Xiang F, Wang H. Fabrication, structure, and property of epoxy-based composites with metal insulator core shell structure fillers. J Mater Res. 2012;28:2644–9.

    Article  Google Scholar 

Download references

Acknowledgements

The authors thank the Head of the Department of Physics, Loyola College, Chennai for providing facilities for conducting dielectric studies.

Author information

Authors and Affiliations

  1. Department of Chemistry, Loyola College, Chennai, 600034, India

    A. Jeya Rajendran, M. Prabhu, K. Eswara Moorthi & I. R. Celine Rose

  2. Department of Chemistry, Vel Tech Dr. Rangarajan Dr. Sakunthala Engineering College, Avadi, Chennai, 600062, India

    D. Santhanaraj

  3. Department of Physics, Loyola College, Chennai, 600034, India

    K. Sugandhi

  4. Department of Physics, S. T. Hindu College, Nagercoil, 629001, Tamilnadu, India

    S. Radhika

Authors
  1. A. Jeya Rajendran
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Prabhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Eswara Moorthi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. R. Celine Rose
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. Santhanaraj
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. Sugandhi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. Radhika
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Jeya Rajendran.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jeya Rajendran, A., Prabhu, M., Eswara Moorthi, K. et al. Dielectric and conductivity studies of stereo-selectively synthesized d- and l-nor-ephedrine. J Therm Anal Calorim 119, 369–379 (2015). https://doi.org/10.1007/s10973-014-4159-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-014-4159-7

Keywords

Search

Navigation