Skip to main content
SpringerLink
Log in

Experimental and DFT studies of ethyl N′-3-(1H-imidazol-1-yl) propylcarbamoyl benzohydrazonate monohydrate

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The Imidazole compound, Ethyl N′-3-(1H-imidazol-1-yl) propylcarbamoyl benzohydrazonate monohydrate, has been synthesized and characterized by IR, NMR, electronic spectroscopy, and X-ray single-crystal determination. Molecular geometry from X-ray experiment of the title compound in the ground state has been compared using the density functional method (B3LYP) with 6-31G+(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by DFT calculations with respect to two selected degrees of torsional freedom, which were varied from −180° to +180° in steps of 10°. Besides, molecular electrostatic potential (MEP), natural bond orbitals (NBO), frontier molecular orbitals (FMO), and thermodynamic properties were performed at B3LYP/6-31G+(d) level of theory.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Zhang Y, Guo ZJ, You XZ (2001) J Am Chem Soc 123:9378. doi:10.1021/ja0023938

    Article  CAS  Google Scholar 

  2. Proft FD, Geerlings P (2001) Chem Rev 101:1451. doi:10.1021/cr9903205

    Article  Google Scholar 

  3. Fitzgerald G, Andzelm J (1991) J Phys Chem 95:10531. doi:10.1021/j100179a003

    Article  CAS  Google Scholar 

  4. Ziegler T (1991) Pure Appl Chem 63:873. doi:10.1351/pac199163060873

    Article  CAS  Google Scholar 

  5. Andzelm J, Wimmer E (1992) J Chem Phys 95:1208

    Google Scholar 

  6. Scuseria GE (1992) J Chem Phys 97:7528. doi:10.1063/1.463977

    Article  CAS  Google Scholar 

  7. Dickson RM, Becke AD (1993) J Chem Phys 99:3898. doi:10.1063/1.466134

    Article  CAS  Google Scholar 

  8. Johnson BG, Gill PMW, Pople JA (1993) J Chem Phys 98:5612. doi:10.1063/1.464906

    Article  CAS  Google Scholar 

  9. Oliphant N, Bartlett RJ (1994) J Chem Phys 100:6550. doi:10.1063/1.467064

    Article  CAS  Google Scholar 

  10. Gilchrist TL (eds) (1997) In: Heterocyclic chemistry, 3rd edn. Chap 8. Longman, Singapore

  11. Grimmett MR (1980) In: Katritzky AR, Boulton AJ (eds) Advances in heterocyclic chemistry, vol 27. Academic Press, New York

    Google Scholar 

  12. Wilkes JS (2002) Green Chem 4:73. doi:10.1039/b110838g

    Article  CAS  Google Scholar 

  13. Welton T (1999) Chem Rev 99:2071. doi:10.1021/cr980032t

    Article  CAS  Google Scholar 

  14. Gu Y, Shi F, Deng Y (2004) J Org Chem 69:391. doi:10.1021/jo0351365

    Article  CAS  Google Scholar 

  15. Rosa JN, Afonso CAM, Santos AG (2001) Tetrahedron 57:4189. doi:10.1016/S0040-4020(01)00316-7

    Article  CAS  Google Scholar 

  16. Kim EJ, Ko SY, Song CE (2003) Helv Chim Acta 86:894. doi:10.1002/hlca.200390087

    Article  CAS  Google Scholar 

  17. Hagiwara R, Ito Y (2000) J Fluor Chem 105:221. doi:10.1016/S0022-1139(99)00267-5

    Article  CAS  Google Scholar 

  18. Gordon CM, Holbrey JD, Kennedy AR, Seddon KR (1998) J Mater Chem 8:2627. doi:10.1039/a806169f

    Article  CAS  Google Scholar 

  19. Stoe Cie (2002) X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany

    Google Scholar 

  20. Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, Germany

    Google Scholar 

  21. Burnett MN, Johnson CK (1996) ORTEP III Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA

    Google Scholar 

  22. Schlegel HB (1982) J Comput Chem 3:163. doi:10.1002/jcc.540030212

    Article  Google Scholar 

  23. Peng C, Ayala PY, Schlegel HB, Frisch MJ (1996) J Comput Chem 17:49. doi:10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0

    Article  CAS  Google Scholar 

  24. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision E.01. Gaussian Inc, Wallingford CT

    Google Scholar 

  25. Frisch A, Dennington RII, Keith T, Millam J, Nielsen AB, Holder AJ, Hiscocks J (2007) GaussView Reference, vol 4.0. Gaussian Inc, Pittsburgh

    Google Scholar 

  26. Politzer P, Landry SJ, Warnheim T (1982) Phys Chem 86:4767. doi:10.1021/j100221a024

    Article  CAS  Google Scholar 

  27. Politzer P, Abrahmsen L, Sjoberg P (1984) J Am Chem Soc 106:855. doi:10.1021/ja00316a005

    Article  CAS  Google Scholar 

  28. Politzer P, Laurence PR, Abrahmsen L, Zilles BA, Sjoberg P (1984) Chem Phys Lett 111:75. doi:10.1016/0009-2614(84)80439-X

    Article  CAS  Google Scholar 

  29. Murray JS, Lane P, Brinck T, Politzer P, Sjoberg P (1991) J Phys Chem 95:14

    Google Scholar 

  30. Zuxing Y, Siping W, Wenhai W, Hua C, Jingbo L (2008) Acta Crystallogr E64:o631

    Google Scholar 

  31. Jian FF, Zhao PS, Bai ZS, Zhang L (2005) Struct Chem 16:635. doi:10.1007/s11224-005-8254-z

    Article  CAS  Google Scholar 

  32. Scrocco E, Tomasi J (1978) Adv Quantum Chem 11:115. doi:10.1016/S0065-3276(08)60236-1

    Article  CAS  Google Scholar 

  33. Luque FJ, Lopez JM, Orozco M (2000) Theor Chem Acc 103:343. doi:10.1007/s002149900013

    CAS  Google Scholar 

  34. Okulik N, Jubert AH (2005) Internet Electron J Mol Des 4:17

    CAS  Google Scholar 

  35. Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, London

    Google Scholar 

  36. Merrick JP, Moran D, Radom L (2007) J Phys Chem A 111:11683. doi:10.1021/jp073974n

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported by the Tubitak Research Fund, Project No. 2007.1407 (Ankara/Turkey).

Author information

Authors and Affiliations

  1. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, Samsun, 55139, Turkey

    Hasan Tanak, Metin Yavuz & Şamil Işık

  2. Samsun Vocational School, Ondokuz Mayıs University, Kurupelit, Samsun, 55139, Turkey

    Yavuz Köysal

  3. Department of Chemistry, Faculty of Arts and Sciences, Karadeniz Technical University, Trabzon, 61080, Turkey

    Yasemin Ünver & Kemal Sancak

Authors
  1. Hasan Tanak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yavuz Köysal
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yasemin Ünver
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Metin Yavuz
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Şamil Işık
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kemal Sancak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hasan Tanak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tanak, H., Köysal, Y., Ünver, Y. et al. Experimental and DFT studies of ethyl N′-3-(1H-imidazol-1-yl) propylcarbamoyl benzohydrazonate monohydrate. Struct Chem 20, 409–416 (2009). https://doi.org/10.1007/s11224-009-9425-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-009-9425-0

Keywords

Search

Navigation