Skip to main content
SpringerLink
Log in

A theoretical study of the structure and aromaticity of nitrogen-containing thiocarbon

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

Abstract

Density functional theory has been used to investigate the structure, stability, and aromaticity of a series of nitrogen-containing thiocarbons, which are related to C n S 2− n (n = 3–5). We have identified a large number of minimum-energy species which might be synthesized and calculated their aromaticity using the nucleus-independent chemical shift (NICS) method of Schleyer and magnetic susceptibility. Successive substitution of carbon by nitrogen reduces their stability, as reflected in the calculated bond orders. In general, there is no close correlation between the stability and π-aromaticity of the species studied.

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

Similar content being viewed by others

References

  1. Cyrañski MK, Krygowski TM, Katritzky AR, Schleyer Pv R (2002) J Org Chem 67:1333–1338

    Article  Google Scholar 

  2. Cyrański MK, Schleyer Pv R, Krygowski TM (2003) Tetrahedron 59:1657–1665

    Article  Google Scholar 

  3. Cyrański MK (2005) Chem Rev 105:3773–3811

    Article  Google Scholar 

  4. Pauling L (1939) J Chem Phys 43:825–839

    Article  Google Scholar 

  5. Katritzky AR, Barczynski P, Musumarra G, Pisano D, Szafran M (1989) J Am Chem Soc 111:7–15

    Article  CAS  Google Scholar 

  6. Katritzky AR, Karelson M, Wells AP (1996) J Org Chem 61:1619–1623

    Article  CAS  Google Scholar 

  7. Krygowski TM, Cyrański MK, Czarnocki Z, Hfelinger G, Katritzky AR (2000) Tetrahedron 56:1783–1796

    Article  CAS  Google Scholar 

  8. London F (1937) J Phys Radium 8:397–409

    Article  CAS  Google Scholar 

  9. Schleyer P v R, Maerker C, Dransfeld A, Jiao H, Hommes N J R v E (1996) J Am Chem Soc 118:6317–6318

    Article  CAS  Google Scholar 

  10. Piekarski AM, Mills NS, Yousef A (2008) J Am Chem Soc 130:14883–14890

    Article  CAS  Google Scholar 

  11. Chen Z, Sutton LR, Moran D, Hirsch A (2001) J Phys Chem A 105:10689–10693

    Article  Google Scholar 

  12. Krygowski TM, Cyrański MK (2001) Chem Rev 101:1385–1420

    Article  CAS  Google Scholar 

  13. Krygowski TM (1993) J Chem Inf Comput Sci 33:70–78

    CAS  Google Scholar 

  14. West R (ed) (1980) Oxocarbons. Academic Press, New York

  15. Serratosa F (1983) Acc Chem Res 16:170–176

    Article  CAS  Google Scholar 

  16. Seitz G, Imming P (1992) Chem Rev 92:1227–1260

    Article  CAS  Google Scholar 

  17. Minkin VI, Glukhovtsev MN, Simkin BY (1994) Aromaticity and antiaromaticity: electronic and structural aspects. Wiley, New York

    Google Scholar 

  18. Schleyer P v R, Jiao H (1996) Pure Appl Chem 68:209–218

    Article  CAS  Google Scholar 

  19. Lloyd D (1996) J Chem Inf Comput Sci 36:442–447

    CAS  Google Scholar 

  20. West R, Niu N-Y, Powell DL, Evans MV (1960) J Am Chem Soc 82:6204–6205

    Article  CAS  Google Scholar 

  21. Schleyer P v R, Najafian K, Kiran B, Jiao H (2000) J Org Chem 65:426–431

    Article  CAS  Google Scholar 

  22. Quinonero D, Frontera A, Ballester P, Deya PM (2000) Tetrahedron Lett 41:2001–2005

    Article  CAS  Google Scholar 

  23. Quinonero D, Garau C, Frontera A, Ballester P, Costa A, Deya PM (2002) Chem Eur J 8:433–438

    Article  CAS  Google Scholar 

  24. Keith TA, Bder RF (1993) Chem Phys Lett 210:223–231

    Article  CAS  Google Scholar 

  25. Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251–8260

    Article  CAS  Google Scholar 

  26. Ditchfield R (1972) J Chem Phys 56:5688–5691

    Article  CAS  Google Scholar 

  27. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven JT, 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, 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 (2003) Gaussian 03, revision B. 03. Gaussian Inc, Pittsburgh, PA

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Wen-Xiu Gu, Li-Juan Xing, Hai-Jun Wang & Zhi-Xiang Song

Authors
  1. Wen-Xiu Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li-Juan Xing
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hai-Jun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhi-Xiang Song
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hai-Jun Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gu, WX., Xing, LJ., Wang, HJ. et al. A theoretical study of the structure and aromaticity of nitrogen-containing thiocarbon. Struct Chem 21, 1221–1226 (2010). https://doi.org/10.1007/s11224-010-9664-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-010-9664-0

Keywords

Search

Navigation