Skip to main content
SpringerLink
Log in

2-METHYLPYRIDINIUM SALT OF PENTAIODOBENZOIC ACID: ROLE OF THE HALOGEN BOND IN THE FORMATION OF A CRYSTAL PACKING

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

In the reaction of pentaiodobenzoic acid (PIBA) and 2-methylpyridine in N,N′-dimethylformamide (2-MePyH)PIBA·DMF salt (1) is formed, whose structure is studied by X-ray crystallography. The structure of 1 contains noncovalent interactions of the I⋯O type of the halogen bond, whose energies are estimated by quantum chemical calculations.

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

Similar content being viewed by others

REFERENCES

  1. G. R. Desiraju, P. S. Ho, L. Kloo, A. C. Legon, R. Marquardt, P. Metrangolo, P. Politzer, G. Resnati, and K. Rissanen. Pure Appl. Chem., 2013, 85, 1711-1713.

    Article  CAS  Google Scholar 

  2. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, and G. Terraneo. Angew. Chem., Int. Ed., 2008, 47, 6114-6127.

    Article  CAS  Google Scholar 

  3. G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, and G. Terraneo. Chem. Rev., 2016, 116, 2478-2601.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. A. S. Mikherdov, A. S. Novikov, V. P. Boyarskiy, and V. Y. Kukushkin. Nat. Commun., 2020, 11, 2921.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. U. Dabranskaya, D. M. Ivanov, A. S. Novikov, Y. V. Matveychuk, N. A. Bokach, and V. Y. Kukushkin. Cryst. Growth Des., 2019, 19, 1364-1376.

    Article  CAS  Google Scholar 

  6. A. A. Eliseeva, D. M. Ivanov, A. S. Novikov, and V. Y. Kukushkin. CrystEngComm, 2019, 21, 616-628.

    Article  CAS  Google Scholar 

  7. M. Bulatova, A. A. Melekhova, A. S. Novikov, D. M. Ivanov, and N. A. Bokach. Z. Kristallogr. - Cryst. Mater., 2018, 233, 371-377.

    Article  CAS  Google Scholar 

  8. I. Yushina, N. Tarasova, D. Kim, V. Sharutin, and E. Bartashevich. Crystals, 2019, 9, 506.

    Article  CAS  Google Scholar 

  9. Y. V. Matveychuk, M. V. Ilkaeva, E. A. Vershinina, V. I. Batalov, R. S. Morozov, and E. V. Bartashevich. J. Mol. Struct., 2016, 1119, 227-234.

    Article  CAS  Google Scholar 

  10. X. Ding, M. J. Tuikka, P. Hirva, V. Y. Kukushkin, A. S. Novikov, and M. Haukka. CrystEngComm, 2016, 18, 1987-1995.

    Article  CAS  Google Scholar 

  11. I. D. Yushina, A. E. Masunov, D. Lopez, A. A. Dyakov, and E. V. Bartashevich. Cryst. Growth Des., 2018, 18, 5069-5079.

    Article  CAS  Google Scholar 

  12. E. A. Katlenok, M. Haukka, O. V. Levin, A. Frontera, and V. Y. Kukushkin. Chem. - Eur. J., 2020, 26, 7692-7701.

    Article  CAS  PubMed  Google Scholar 

  13. J. K. Salunke, N. A. Durandin, T.-P. Ruoko, N. R. Candeias, P. Vivo, E. Vuorimaa-Laukkanen, T. Laaksonen, and A. Priimagi. Sci. Rep., 2018, 8, 14431.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. J. J. Brown, A. J. Brock, M. C. Pfrunder, J. P. Sarju, A. Z. Perry, A. C. Whitwood, D. W. Bruce, J. C. McMurtrie, and J. K. Clegg. Aust. J. Chem., 2017, 70, 594-600.

    Article  CAS  Google Scholar 

  15. V. V. Sivchik, A. I. Solomatina, Y.-T. Chen, A. J. Karttunen, S. P. Tunik, P.-T. Chou, and I. O. Koshevoy. Angew. Chem., Int. Ed., 2015, 54, 14057-14060.

    Article  CAS  Google Scholar 

  16. Y. V. Torubaev, D. K. Rai, I. V. Skabitsky, S. Pakhira, and A. Dmitrienko. New J. Chem., 2019, 43, 7941-7949.

    Article  CAS  Google Scholar 

  17. L. E. Zelenkov, D. M. Ivanov, M. S. Avdontceva, A. S. Novikov, and N. A. Bokach. Z. Kristallogr. - Cryst. Mater., 2019, 234, 9-17.

    Article  CAS  Google Scholar 

  18. A. M. Afanasenko, M. S. Avdontceva, A. S. Novikov, and T. G. Chulkova. Z. Kristallogr. - Cryst. Mater., 2016, 231, 435-440.

    Article  CAS  Google Scholar 

  19. D. M. Ivanov, A. S. Novikov, G. L. Starova, M. Haukka, and V. Y. Kukushkin. CrystEngComm, 2016, 18, 5278-5286.

    Article  CAS  Google Scholar 

  20. A. S. Novikov, D. M. Ivanov, M. S. Avdontceva, and V. Y. Kukushkin. CrystEngComm, 2017, 19, 2517-2525.

    Article  CAS  Google Scholar 

  21. Y. V. Torubaev, I. V. Skabitsky, G. A. Saratov, and P. Y. Barzilovich. Mendeleev Commun., 2021, 31, 58-61.

    Article  CAS  Google Scholar 

  22. Y. V. Torubaev and I. V. Skabitsky. Z. Kristallogr. - Cryst. Mater., 2020, 235, 599-607.

    Article  CAS  Google Scholar 

  23. Y. V. Torubaev, K. A. Lyssenko, and A. E. Popova. Russ. J. Coord. Chem., 2019, 45, 788-794.

    Article  CAS  Google Scholar 

  24. Y. V. Torubaev, I. V. Skabitskiy, P. Rusina, A. A. Pasynskii, D. K. Rai, and A. Singh. CrystEngComm, 2018, 20, 2258-2266.

    Article  CAS  Google Scholar 

  25. Y. V. Torubaev, A. A. Pasynskii, A. V. Pavlova, and M. M. Shaikh. Mendeleev Commun., 2017, 27, 141-143.

    Article  CAS  Google Scholar 

  26. T. A. Shestimerova, N. A. Yelavik, A. V. Mironov, A. N. Kuznetsov, M. A. Bykov, A. V. Grigorieva, V. V. Utochnikova, L. S. Lepnev, and A. V. Shevelkov. Inorg. Chem., 2018, 57, 4077-4087.

    Article  CAS  PubMed  Google Scholar 

  27. T. A. Shestimerova, N. A. Golubev, N. A. Yelavik, M. A. Bykov, A. V. Grigorieva, Z. Wei, E. V. Dikarev, and A. V. Shevelkov. Cryst. Growth Des., 2018, 18, 2572-2578.

    Article  CAS  Google Scholar 

  28. Y. V. Torubaev, I. V. Skabitskiy, A. V. Pavlova, and A. A. Pasynskii. New J. Chem., 2017, 41, 3606-3611.

    Article  CAS  Google Scholar 

  29. O. B. Ryabchenko, L. A. Kuarton, and I. V. Svistunova. J. Mol. Struct., 2021, 1227, 129532.

    Article  CAS  Google Scholar 

  30. N. G. Shikhaliyev, A. M. Maharramov, G. T. Suleymanova, G. V. Babayeva, G. Z. Mammadova, I. M. Shikhaliyeva, A. A. Babazade, and V. G. Nenajdenko. ARKIVOC, 2021, 2021, 67-75.

    Article  CAS  Google Scholar 

  31. V. G. Nenajdenko, N. G. Shikhaliyev, A. M. Maharramov, K. N. Bagirova, G. T. Suleymanova, A. S. Novikov, V. N. Khrustalev, and A. G. Tskhovrebov. Molecules, 2020, 25, 5013.

    Article  CAS  PubMed Central  Google Scholar 

  32. N. S. Soldatova, V. V. Suslonov, T. Y. Kissler, D. M. Ivanov, A. S. Novikov, M. S. Yusubov, P. S. Postnikov, and V. Y. Kukushkin. Crystals, 2020, 10, 230.

    Article  CAS  Google Scholar 

  33. P. Smart, Á. Bejarano-Villafuerte, R. M. Hendry, and L. Brammer. CrystEngComm, 2013, 15, 3160-3167.

    Article  CAS  Google Scholar 

  34. Ö. Aydın, N. Çaylak Delibaş, H. Necefoğlu, and T. Hökelek. Acta Crystallogr., Sect. E: Struct. Rep. Online, 2012, 68, m409-m410.

    Article  Google Scholar 

  35. J. A. Ridenour, K. P. Carter, and C. L. Cahill. CrystEngComm, 2017, 19, 1190-1203.

    Article  CAS  Google Scholar 

  36. K. P. Carter, M. Kalaj, A. Kerridge, and C. L. Cahill. CrystEngComm, 2018, 20, 4916-4925.

    Article  CAS  Google Scholar 

  37. M. Kalaj, K. P. Carter, A. V. Savchenkov, M. M. Pyrch, and C. L. Cahill. Inorg. Chem., 2017, 56, 9156-9168.

    Article  CAS  PubMed  Google Scholar 

  38. J. Halaška, A. Pevec, Z. Růžičková, M. K. Lawson, M. Koman, M. Valko, B. Kozlevčar, and J. Moncol. Monatsh. Chem., 2018, 149, 1017-1030.

    Article  CAS  Google Scholar 

  39. M. A. Shmelev, G. N. Kuznetsova, F. M. Dolgushin, Y. K. Voronina, N. V. Gogoleva, M. A. Kiskin, V. K. Ivanov, A. A. Sidorov, and I. L. Eremenko. Russ. J. Coord. Chem., 2021, 47, 127-143.

    Article  CAS  Google Scholar 

  40. M. A. Shmelev, N. V. Gogoleva, G. N. Kuznetsova, M. A. Kiskin, Y. K. Voronina, I. A. Yakushev, T. M. Ivanova, Y. V. Nelyubina, A. A. Sidorov, and I. L. Eremenko. Russ. J. Coord. Chem., 2020, 46, 557-572.

    Article  CAS  Google Scholar 

  41. M. V. Chernysheva, M. Bulatova, X. Ding, and M. Haukka. Cryst. Growth Des., 2020, 20, 7197-7210.

    Article  CAS  Google Scholar 

  42. D. L. Mattern. J. Org. Chem., 1984, 49, 3051-3053.

    Article  CAS  Google Scholar 

  43. S. A. Adonin, M. A. Bondarenko, A. S. Novikov, P. A. Abramov, M. N. Sokolov, and V. P. Fedin. CrystEngComm, 2019, 21, 6666-6670.

    Article  CAS  Google Scholar 

  44. G. M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3-8.

    Article  Google Scholar 

  45. A. Bondi. J. Phys. Chem., 1966, 70, 3006-3007.

    Article  CAS  Google Scholar 

  46. J. Da Chai and M. Head-Gordon. Phys. Chem. Chem. Phys., 2008, 10, 6615-6620.

    Article  CAS  PubMed  Google Scholar 

  47. C. L. Barros, P. J. P. de Oliveira, F. E. Jorge, A. Canal Neto, and M. Campos. Mol. Phys., 2010, 108, 1965-1972.

    Article  CAS  Google Scholar 

  48. A. Canal Neto and F. E. Jorge. Chem. Phys. Lett., 2013, 582, 158-162.

    Article  CAS  Google Scholar 

  49. R. C. de Berrêdo and F. E. Jorge. J. Mol. Struct.: THEOCHEM, 2010, 961, 107-112.

    Article  CAS  Google Scholar 

  50. F. E. Jorge, A. Canal Neto, G. G. Camiletti, and S. F. Machado. J. Chem. Phys., 2009, 130, 064108.

    Article  CAS  PubMed  Google Scholar 

  51. R. F. W. Bader. Chem. Rev., 1991, 91, 893-928.

    Article  CAS  Google Scholar 

  52. T. Lu and F. Chen. J. Comput. Chem., 2012, 33, 580-592.

    Article  CAS  PubMed  Google Scholar 

  53. A. A. Eliseeva, D. M. Ivanov, A. S. Novikov, A. V. Rozhkov, I. V. Kornyakov, A. Y. Dubovtsev, and V. Y. Kukushkin. Dalton Trans., 2020, 49, 356-367.

    Article  CAS  PubMed  Google Scholar 

  54. M. A. Kinzhalov, A. A. Eremina, D. M. Ivanov, A. S. Novikov, E. A. Katlenok, K. P. Balashev, and V. V. Suslonov. Z. Kristallogr. - Cryst. Mater., 2017, 232, 797-805.

    Article  CAS  Google Scholar 

  55. A. S. Novikov, D. M. Ivanov, Z. M. Bikbaeva, N. A. Bokach, and V. Y. Kukushkin. Cryst. Growth Des., 2018, 18, 7641-7654.

    Article  CAS  Google Scholar 

  56. E. V Bartashevich and V. G. Tsirelson. Russ. Chem. Rev., 2014, 83, 1181-1203.

    Article  CAS  Google Scholar 

Download references

Funding

The work was supported by RFBR (project No. 20-33-70010).

Author information

Authors and Affiliations

  1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    M. A. Bondarenko, M. N. Sokolov & S. A. Adonin

  2. St. Petersburg State University, St. Petersburg, Russia

    A. S. Novikov

  3. Kazan (Volga region) Federal University, Butlerov Institute of Chemistry, Kazan, Russia

    M. N. Sokolov

  4. Irkutsk National Research Technical University, Irkutsk, Russia

    K. V. Chernova

Authors
  1. M. A. Bondarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. V. Chernova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. N. Sokolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. A. Adonin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Adonin.

Ethics declarations

The authors declare that they have no conflict of interests.

Additional information

Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 8, pp. 1325-1330.https://doi.org/10.26902/JSC_id78529

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bondarenko, M.A., Novikov, A.S., Chernova, K.V. et al. 2-METHYLPYRIDINIUM SALT OF PENTAIODOBENZOIC ACID: ROLE OF THE HALOGEN BOND IN THE FORMATION OF A CRYSTAL PACKING. J Struct Chem 62, 1237–1242 (2021). https://doi.org/10.1134/S0022476621080096

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476621080096

Keywords

Search

Navigation