Skip to main content
SpringerLink
Log in

An unusually stable pyridine-2-selenenyl chloride: structure and reactivity

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

Abstract

According to an X-ray diffraction study, pyridine-2-selenenyl chloride (1) characterized by unusually high stability both in solutions and in the solid state adopts a dimeric structure formed by two secondary intermolecular Se···N interactions. However, it slowly transforms into zwitterionic T-shaped pyridinium-2-selenenyl dichloride (2) in a dichloromethane solution. Conformational features, electronic structures, and reactivities of 1 and 2 are discussed on the basis of experimental and theoretical (quantum chemical calculations) data.

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
Scheme 1
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. du Mont W-W, Kubiniok S, Peters K, von Schnering H-G (1987) Angew Chem Int Ed Engl 26:780–781

    Article  Google Scholar 

  2. Klapötke TM, Krumm B, Mayer P, Piotrowski H, Vogt M (2003) Z Anorg Allg Chem 629:1117–1123

    Article  Google Scholar 

  3. Back TG, Moussa Z, Parvez M (2004) Phosphorus Sulfur Silicon 179:2569–2579

    Article  CAS  Google Scholar 

  4. Ranganathan S, Muraleedharan KM, Vaish NK, Jayaraman N (2004) Tetrahedron 60:5273–5308

    Article  CAS  Google Scholar 

  5. Młochowski J (2008) Phosphorus Sulfur Silicon 183:931–938

    Article  Google Scholar 

  6. Klapötke TM, Krumm B, Polborn K (2008) Z Anorg Allg Chem 634:1287–1290

    Article  Google Scholar 

  7. Mukherjee AJ, Zade SS, Singh HB, Sunoj RB (2010) Chem Rev 110:4357–4416

    Article  CAS  Google Scholar 

  8. Selvakumar K, Singh HB, Butcher RJ (2010) Chem Eur J 16:10576–10591

    Article  CAS  Google Scholar 

  9. Drabowicz J, Midura WH, Krasowska D (2011) Selenium and tellurium (1,2,3)-oxygen-containing acids and derivatives. In: Rappoport Z (ed) The chemistry of organic selenium and tellurium compounds. Wiley, New York, pp 1027–1082

    Google Scholar 

  10. Selvakumar K, Singh VP, Shah P, Singh HB (2011) Main Group Chem 10:141–152

    CAS  Google Scholar 

  11. Pöllnitz A, Lippolis V, Arca M, Silvestru A (2011) J Organomet Chem 696:2837–2844

    Article  Google Scholar 

  12. Santi C, Santoro S (2012) In: Wirth T (ed) Organoselenium chemistry: synthesis and reactions, 1st edn. Wiley, New York

    Google Scholar 

  13. Zade SS, Singh HB (2014) Synthesis of organoselenium compounds. In: Rappoport Z, Liebman JF, Marek I, Patai S (eds) The chemistry of organic selenium and tellurium compounds, vol 4. Wiley, New York, pp 1–180

    Google Scholar 

  14. Santi C, Tidei C (2014) Electrophilic selenium/tellurium reagents: reactivity and their contribution to green chemistry. In: Rappoport Z, Liebman JF, Marek I, Patai S (eds) The chemistry of organic selenium and tellurium compounds, vol 4. Wiley, New York, pp 569–656

    Google Scholar 

  15. Nakanishi W, Hayashi S, Hashimoto M, Arca M, Aragoni MC, Lippolis V (2013) Recent advances of structural chemistry of organoselenium and organotellurium compounds. In: Organic selenium and tellurium. John Wiley & Sons, Ltd., New York

  16. Borisov AV, Matsulevich ZhV, Fukin GK, Baranov EV (2010) Russ Chem Bull 59:581–583

    Article  CAS  Google Scholar 

  17. Toshimitsu A, Owada H, Terao K, Uemura S, Okano M (1984) J Org Chem 49:3796–3800

    Article  CAS  Google Scholar 

  18. Khrustalev VN, Matsulevich ZV, Lukiyanova JM, Aysin RR, Peregudov AS, Leites LA, Borisov AV (2014) Eur J Inorg Chem (22):3582–3586

  19. Borisov AV, Matsulevich ZhV (2009) Chem Heterocycl Compd 45:884–885

    Article  CAS  Google Scholar 

  20. Borisov AV, Matsulevich ZhV, Osmanov VK, Borisova GN, Naumov VI, Mammadova GZ, Maharramov AM, Khrustalev VN, Kachala VV (2012) Russ Chem Bull 61:91–94

    Article  CAS  Google Scholar 

  21. Sheldrick GM (2003) SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin

  22. Sheldrick GM (2008) Acta Crystallogr A 64:112–122

    Article  CAS  Google Scholar 

  23. 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, AlLaham 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

    Google Scholar 

  24. Perdew JP, Burke K, Ernzerhof M (1997) Phys Rev Lett 78:1396

    Article  CAS  Google Scholar 

  25. Zhao Y, Truhlar DG (2008) Theor Chem Acc 120:215–241

    Article  CAS  Google Scholar 

  26. Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650–654

    Article  CAS  Google Scholar 

  27. McLean AD, Chandler GS (1980) J Chem Phys 72:5639–5648

    Article  CAS  Google Scholar 

  28. AIMAll (Version 14.11.23), Keith TA (2014) TK Gristmill Software, Overland Park KS, USA (aim.tkgristmill.com)

  29. Cambridge Structural Database, Release 2016, Cambridge, UK.

  30. Khrustalev VN, Ismaylova SR, Aysin RR, Matsulevich ZV, Osmanov VK, Peregudov AS, Borisov AV (2012) Eur J Inorg Chem (33):5456–5460

  31. Minyaev RM, Orlova GV (1985) J Struct Chem 26:157–164

    Article  Google Scholar 

  32. Demartin F, Devillanova FA, Isaia F, Lippolis V, Boyle PD, Godfrey SM (2000) J Chem Soc Dalton Trans (12):1959–1960

  33. Mammadova GZ, Matsulevich ZhV, Osmanov VK, Borisov AV, Khrustalev VN (2012) Acta Crystallogr Sect E 68:o1381

    Article  CAS  Google Scholar 

  34. Mammadova GZ, Matsulevich ZhV, Osmanov VK, Borisov AV, Khrustalev VN (2011) Acta Crystallogr Sect E 67:o3050

    Article  CAS  Google Scholar 

  35. Husebye S, Lindeman SV, Rudd MD (1997) Acta Crystallogr Sect C 53:809–811

    Article  Google Scholar 

  36. Makarov AG, Makarov AYu, Bagryanskaya IYu, Shakirov MM, Zibarev AV (2012) J Fluor Chem 144:118–123

    Article  CAS  Google Scholar 

  37. Espinosa E, Molins E, Lecomte C (1998) Chem Phys Lett 285:170–173

    Article  CAS  Google Scholar 

  38. Borisov AV, Osmanov VK, Borisova GN, Matsulevich ZV, Fukin GK (2009) Mendeleev Commun 19(1):49–51

    Article  CAS  Google Scholar 

  39. Borisov AV, Matsulevich ZV, Osmanov VK, Borisova GN, Fukin GK (2010) 2-Pyridineselenenyl- and tellurenyl chlorides as building blocks for derivatives of 2,3-dihydro[1,3]selen(tellur)azolo[3,2-a]pyridin-4-ium. In: Nylund K, Johansson P (eds) Heterocyclic compounds: synthesis, properties and applications. Nova Science Publishers Inc, New York, pp 211–218

    Google Scholar 

  40. Borisov AV, Matsulevich ZhV, Osmanov VK, Borisova GN, Savikhina EV (2007) Chem Heterocycl Compd 43:525–526

    Article  CAS  Google Scholar 

  41. Borisov AV, Matsulevich ZhV, Tyurin YuM (2011) Chem Heterocycl Compd 47:649–650

    Article  CAS  Google Scholar 

  42. Borisov AV, Matsulevich ZhV, Osmanov VK, Borisova GN (2012) Chem Heterocycl Compd 48:492–496

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the Russian Foundation for Basic Research (Grant No. 14-03-00914) and the Russian Academy of Sciences in the framework of the program “Theoretical and experimental study of chemical bonding and mechanisms of chemical reactions and processes” for financial support of this work.

Author information

Authors and Affiliations

  1. Peoples’ Friendship University of Russia, Miklukho-Maklay St., 6, Moscow, Russian Federation, 117198

    Victor N. Khrustalev

  2. A. N. Nesmeyanov Institute of Organoelement Compounds of RAS, Vavilov St., 28, Moscow, Russian Federation, 119991

    Victor N. Khrustalev & Rinat R. Aysin

  3. R. E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, Nizhny Novgorod, Russian Federation, 603950

    Zhanna V. Matsulevich, Julia M. Lukiyanova & Alexander V. Borisov

  4. G. A. Razuvaev Institute of Metalloorganic Chemistry of RAS, Tropinin St., 49, Nizhny Novgorod, Russian Federation, 603137

    Georgy K. Fukin

  5. National Research Center “Kurchatov Institute”, Acad. Kurchatov Sq., 1, Moscow, Russian Federation, 123182

    Yan V. Zubavichus

  6. Baku State University, Z. Khalilov St., 23, 1148, Baku, Azerbaijan

    Rizvan K. Askerov & Abel M. Maharramov

Authors
  1. Victor N. Khrustalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhanna V. Matsulevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rinat R. Aysin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Julia M. Lukiyanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Georgy K. Fukin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yan V. Zubavichus
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Rizvan K. Askerov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Abel M. Maharramov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Alexander V. Borisov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Victor N. Khrustalev.

Additional information

This paper is dedicated to Prof. Vladimir Shevchenko (Institute of Silicate Chemistry of Russian Academy of Sciences, Saint-Petersburg, Russia) on the occasion of his 75th anniversary.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khrustalev, V.N., Matsulevich, Z.V., Aysin, R.R. et al. An unusually stable pyridine-2-selenenyl chloride: structure and reactivity. Struct Chem 27, 1733–1741 (2016). https://doi.org/10.1007/s11224-016-0845-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-016-0845-3

Keywords

Search

Navigation