Skip to main content
SpringerLink
Log in

Crystal and Molecular Structure of Two Organic Salts from 3,5-Dimethylpyrazole and Organic Acids

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Two compounds (3,5-dimethylpyrazole): (4-nitro-phthalic acid) (1) [(HL)+·(Hnpa)−, Hnpa = 4-nitro-hydrogenphthalate], and (3,5-dimethylpyrazole): (naphthalene-1,5-disulfonic acid) (2) [(HL+)2·(nds2−), nds2− = 1,5-naphthalenedisulfonate] were obtained from self-assembly of the corresponding acids with the 3,5-dimethylpyrazole, and their structures were fully characterized. Both compounds are ionic, with proton transfer occurring to the N of the 3,5-dimethylpyrazole moiety. The two structures adopted hetero supramolecular synthons. Compound 1 crystallizes in the monoclinic, space group P2(1), with a = 7.843(3) Å, b = 6.8506(12) Å, c = 12.816(2) Å, β = 92.0710(10)°, V = 688.1(3) Å3, Z = 2. Compound 2 crystallizes in the triclinic, space group P-1, with a = 8.0883(13) Å, b = 8.2960(15) Å, c = 8.9223(14) Å, α = 75.502(14)°, β = 89.975(13)°, γ = 80.197(14)°, V = 570.60(16) Å3, Z = 1. Supramolecular architectures of the compounds 1–2 involve O–H···O/N–H···O/N–H···S hydrogen bonds as well as other noncovalent associations. The role of these noncovalent interactions in the crystal packing is analysed. Both salts displayed 3D framework structure for the synergistic effect of the various noncovalent interactions.

Graphical Abstract

The crystal structures of the 3,5-dimethylpyrazole salts with 4-nitro-phthalic acid, and naphthalene-1,5-disulfonic acid show extensive hydrogen bonding as well as C–H···O, CH3···O, and C···π interections, giving three-dimensional networks.

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
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Janiak CJ (2000) J Chem Soc Dalton Trans 21:3885

    Article  Google Scholar 

  2. Desiraju GR (2005) Chem Commun 224:2995

    Article  Google Scholar 

  3. Lehn JM, Atwood JL, Davies JED, MacNicol DD, Vögtle F (1996) (Eds) Comprehensive Supramolecular Chemistry, Pergamon, Oxford, UK

  4. Wood PA, Allen FH, Pidcock E (2009) CrystEngComm 11:1563

    Article  CAS  Google Scholar 

  5. Veljković DŽ, Janjić GV, Zarić SD (2011) CrystEngComm 13:5005

    Article  Google Scholar 

  6. Desiraju GR (2011) Cryst Growth Des 11:896

    Article  CAS  Google Scholar 

  7. Burrows AD (2004) Struct Bonding 108:55

    Article  CAS  Google Scholar 

  8. Braga D, Maini L, Polito M, Grepioni F (2004) Struct Bonding 111:1

    Article  CAS  Google Scholar 

  9. Aakeröy CB, Beatty AM (2001) Aust J Chem 54:409

    Article  Google Scholar 

  10. Etter MC (1990) Acc Chem Res 23:120

    Article  CAS  Google Scholar 

  11. Holman KT, Pivovar AM, Swift JA, Ward MD (2001) Acc Chem Res 34:107

    Article  CAS  Google Scholar 

  12. Gould PJ (1986) Int J Pharm 33:201

    Article  CAS  Google Scholar 

  13. Shan N, Bond AD, Jones W (2002) Cryst Eng 5:9

    Article  CAS  Google Scholar 

  14. Bhogala BR, Basavoju S, Nangia A (2005) CrystEngComm 7:551

    Article  CAS  Google Scholar 

  15. Desiraju GR (1989) Crystal engineering. The design of organic solids. Elsevier, Amsterdam

    Google Scholar 

  16. Leiserowitz L (1976) Acta Crystallogr B32:775

    Article  CAS  Google Scholar 

  17. Kolotuchin SV, Fenlon EE, Wilson SR, Loweth CJ, Zimmerman SC (1995) Angew Chem Int Ed Engl 34:2654

    Article  CAS  Google Scholar 

  18. Kuduva SS, Craig DC, Nangia A, Desiraju GR (1999) J Am Chem Soc 121:1936

    Article  CAS  Google Scholar 

  19. MacDonald JC, Dorrestein PC, Pilley MM (2001) Cryst Growth Des 1:29

    Article  CAS  Google Scholar 

  20. Highfill ML, Chandrasekaran A, Lynch DE, Hamilton DG (2002) Cryst Growth Des 2:15

    Article  CAS  Google Scholar 

  21. Vishweshwar P, Nangia A, Lynch VM (2002) J Org Chem 67:556

    Article  CAS  Google Scholar 

  22. Nichol GS, Clegg W (2009) Cryst Growth Des 9:1844

    Article  CAS  Google Scholar 

  23. Men YB, Sun JL, Huang ZT, Zheng QY (2009) CrystEngComm 11:978

    Article  CAS  Google Scholar 

  24. Wei SS, Jin SW, Hu ZF, Zhou Y, Zhou YP (2012) Acta Cryst E68:o3117

    Google Scholar 

  25. Xu YC, Jin SW, Zhu JL, Liu YJ, Shi CC (2011) Acta Cryst E67:o2528

    Google Scholar 

  26. Jin SW, Zhang WB, Liu L, Gao HF, Wang DQ, Chen RP, Xu XL (2010) J Mol Struct 975:128

    Article  CAS  Google Scholar 

  27. Jin SW, Zhang WB, Liu L, Wang DQ, He HD, Shi T, Lin F (2011) J Mol Struct 991:1

    Article  CAS  Google Scholar 

  28. Jin SW, Liu L, Wang DQ, Guo JZ (2011) J Mol Struct 1005:59

    Article  CAS  Google Scholar 

  29. Jin SW, Wang DQ, Wang XL, Guo M, Zhao QJ (2008) J Inorg Organomet Polym 18:300

    Article  CAS  Google Scholar 

  30. Bruker, Smart and Saint. Bruker AXS, Madison (2004)

  31. Sheldrick GM (2000) SHELXTL, Structure determination Software Suite, version 6.14. Bruker AXS, Madison

  32. Dale SH, Elsegood MRJ, Hemmings M, Wilkinson AL (2004) CrystEngComm 6:207

    Article  CAS  Google Scholar 

  33. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support of the Zhejiang Provincial Natural Science Foundation (LY14B010006), the financial support of the Education Office Foundation of Zhejiang Province (Project No. Y201017321) and the financial support of the Zhejiang A & F University Science Foundation (Project No. 2009FK63).

Author information

Authors and Affiliations

  1. Tianmu College ZheJiang A & F University, Zhuji, 311800, People’s Republic of China

    Shouwen Jin, Jing Zhang, MengJia Zhou, Lin Tao & Yinyan Shen

  2. Department of Chemistry, Liaocheng University, Liaocheng, 252059, People’s Republic of China

    Daqi Wang

Authors
  1. Shouwen Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Daqi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jing Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. MengJia Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lin Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yinyan Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shouwen Jin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jin, S., Wang, D., Zhang, J. et al. Crystal and Molecular Structure of Two Organic Salts from 3,5-Dimethylpyrazole and Organic Acids. J Chem Crystallogr 44, 394–400 (2014). https://doi.org/10.1007/s10870-014-0528-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-014-0528-0

Keywords

Search

Navigation